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Perfect Holiday

Perfect Holiday

by: christine

When we boarded the plane, everything looked like I was going on the holiday of my dreams – and I was – although it was a holiday I had never dared to dream of. Sitting next to me on the plane was Julie, my lovely girlfriend. She is quite tall and not what you would call a full figure, she has rather small tits, a slim figure and long legs. She never dresses “sexy” like us men would like the girls to but she sure turnes some heads when we go out. So, after a long time of both of us working in our jobs we were finally off to our hard-earned vacation in the sun.

When we finally got off the plane after ten hours of a daytime flight, we got stuck at the baggage-claim. Her suitcase – always twice the size of mine, got out right away but we waited for mine till the moving band stopped.

“So” I said. “I guess that’s it. We gotta talk to lost and found.” And we did that, went through the charts and I described my aluminum suitcase, its contents and sure, I had my nametag on it all right. We grabbed a cab after spending two hours at the airport and arrived at the hotel all wasted and smelling like a person who has just spent an entire day in his clothes. You know what your clothes are like after a flight like this. The receptionist didn’t care, I guess she was used to this. I left a note that should my luggage arrive I wanted to be notified immediately.

The room was finally a break. A great bed, a spacious bathroom with a separate restroom and a nice balcony with an oceanview. While I was checking out the remote and buzzed through the channels, Julie hopped into the shower. After twenty minutes she got out and kissed me. “Oh Dear” she said, “you could use a shower, too!” – “Yeah, I know” I answered. She started to drag some fresh clothes out of her suitcase. A thong, a tanktop and an ankle-long skirt. “Problem is, I wont have anything to wear after the shower.” – “Don’t worry, sweetie, your suitcase can be over here any minute.”

So I went into the shower. There was the reason for her twenty-minute-shower, her lady’s razor. She always got carried away shaving her legs and yes, her clit. She always spared plenty of hair on top of it but started to shave her labia a while ago. I suggested it, because I love to eat her out and she loves it too and she agreed that her hair doesn’t really help the licking and sucking. I had asked her to shave me once, and she did, but she didn’t like the feel of my “sparks” as she would like to call the short hair growing back rubbing on her clit. But for me it was quite a sensation to see my naked cock and feel my soft skin touch her clit. Anyways, I sometimes used her razor to shave around my balls and my “bikini-line” as they call it in the women’s mags. And so I did now, making sure I could quickly put the razor away, in case she’d come in. Even more difficult was avoiding a hard-on from shaving, but after years of practice I could do without. And she didn’t come in. I got out of the bathroom with a towel wrapped around my waist. My clothes, which had been spread out on the bed, were gone. “Julie, where’d you put my clothes?” – “I had the laundry guy come and pick them up.” – “But what am I gonna wear for dinner?” – “Don’t worry honey, dinner won’t be before eight and the laundry guy said he’ll be back at 7.30.” – “Okay, but….” – “Don’t be silly honey, you couldn’t have worn this for dinner!” And she was right, again.

“Come on over honey, I have something in mind that doesn’t require any clothes” she added. And she lay me down on bed, on my back and climbed on top of me, undressing herself. She started rubbing her chest at mine and took off my towel. “C’mon baby, caress my little pussy, make it moist and lick me off, won’t you?” I didn’t need any further asking. I used my fingers on her labia and boy it felt good to touch that freshly shaved pussy. I turned her around and buried my head between her legs. I licked and sucked and swallowed all I could. I love the taste I love the sensation I love just to please HER. And what better way to do that than licking her into a frenzy. After a while she rolled back on top of me and started rubbing her clit on my dick and balls while pressing them on my belly. She usually drives me really crazy doing this and she knows it. She only doesn’t know, why, I always thought. I love being her “toy” and getting her off without fucking her, i.e. me entering her sacred pussy. Finally, I’m allowed to enter her. She rolls over, grabs my penis and my balls with one hand and drags my manhood into her, gives it a few strokes and I can’t help to come right away. The feeling of her being in control of my dick, fucking herself with it like a dildo turns me on so much, I can never hold my juices for long. And she knows that for sure. But I thought that she loves it when I get off and that’s why she does it – not cause she knows what I’m feeling and thinking, while she’s doing it to me.

I roll over to my back and slide out off her pussy. I would love to lick her clean now, but I just don’t dare to mention these things. She gets up, takes another shower, and gets dressed, while I also showered again.

It was close to 7:30 and I was still hanging around our hotel room with a towel around my thighs with my girlfriend dressed up and made up for dinner. “Hon, when’d you say the laundry will come?” – “Seven thirty, but you can call housekeeping to make sure. Dial 6 or 7.” I called and received some exciting news. Sure, they said, laundry will be there at 7:30, tomorrow morning that is! I stuttered something like “Sure thanks!” and was perplexed for the moment. “Anything wrong, honey?” I burst out laughing. “My clothes won’t be here before 7:30 tomorrow morning.” Julie started giggling. “Looks like I’m gonna call roomservice and have dinner here.” – “O no darling, you just can’t do that.” – “But Julie, I…” – “Tonight’s the receptioning dinner and you know that, too. There’s a special six-course dinner and I want to start enjoying my vacation as it is with you starting right now.” – “But Julie, there’s no…” – “Don’t be silly, darling, I’m sure we can find something for you to wear in my suitcase. It’s not like I only brought a miniskirt.” She was very insisting and I know there was no use in trying to start an argument over this. She’d burst into tears in no time and we’d have a relationship from hell for two straight days.

“Okay honey I’ll try and do it for you. Let’s see what you got for me.” Julie quickly started to look through her suitcase and produced a number of clothes for me to try on. It was not silk and laces but it all had some distinct feminine touch to it. First she inspected her assortment of panties and ended up handing me two to choose from: A white silk french knicker “loose fit!” she commented, and a pink plain cotton slip with floral ornaments and a cotton-coated button on the front “the regular one”. Then she handed me loose khaki pants with sort of like a ribbon to tie them up at the waist. “I’m sure you’ll manage to get into them!” And her denim pants. “But you probably won’t be able to slip into them.” Next came a loose shortsleeve white linen blouse and a grey blouse with a trimmed waist cut. “Hurry up honey, try it all on, we don’t want to be late for dinner.” I had all the clothes piled up on my arms. I started to head towards the bathroom, I was too embarrassed to change in front of her. “Where are you going, darling. I want to see how it looks on you.” I started to feel a little tension building up against the towel wrapped around my thighs. I couldn’t help feeling a little aroused. Just like I use to, when I’m shaving. But I know how to handle this. Just think of something completely different, something about my job. And it did the trick! I quickly slid on the pink cotton slip – and there it was again. Uncontrollable this time. My dick started pounding and swelling. And this panty slip was so little, it would hardly contain my cock and balls anyways. I turned away from Julie in embarrassment. “Turn around, I want to see you!” I did as she told me. Why?

“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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This sissy is with You now for off and on 3-4 years and slowly but surely she gets Your program and discovers her true nature. In the beginning she was just a sissy on occasion and at “certain” times. But… Read more “sissychelle”

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It was really great to know this site. i have obviously missed a lot not getting onto this site before. your suggestions will definitely make this slut a better maid and keep her Mistress happy and satisfied forever. this whore’s… Read more “diana”

This sissy is infinitely grateful that you have welcomed her into the House and given her a safe haven among like-minded people. Although she has only been here for a short time, she has made tremendous progress in her deep… Read more “sissy fraenzi”

my Wife has ordered me to write You again and tell You how much She enjoys Your site and the ideas it has given Her. She says She never realized how nice it would be to have a sissy maid/slut… Read more “kelli ann”

It is now almost three months since my Wife and i have begun reading your site, and it has made a radical difference in Her approach to my feminization. She has decided, much to my humiliation, that i must be… Read more “sondra”

i just wanted to drop a line to say that Your web-site, “The House Of Sissify” is an artistic masterpiece (mistress-piece?) . .. it is alluring, entrancing, enchanting,exotic, exhilarating, breathtaking, mystifying, and sanctifying. Every page opens ones mind, heart and… Read more “michaela”

i would like to thank you for the information and amusement Youve given me. This really is a mind teasing site. informative, educative, seductive and fun at the same time.

This sissy wishes to thank her Superiors for providing the opportunity for learning. This sissy is so happy at being able to learn how to be a better sissy.Thank you for providing such great insight, and for allowing this sissy… Read more “sissy michelle”

Joining The House has been the best thing ever for this sissy. It has been about a week since joining and already sissy feels a tremendous turnaround in the way she feels and acts. she most certainly feels more feminine,… Read more “bobbiegirl”

This site is SOOOOO cool. Very well done & intelligent. Great graphics & a great staff. I even met someone & we are going to get together soon thanks to the International Sissy Network

Thanks for the chat room You have provided for us sissies. The help from my sisters has been wonderful.

i am so happy to have found your site, my Master sent me here. i am looking forward to becoming the perfect sissy slave, trained for the pleasure of others. Your site has given me real hope of achieving this… Read more “sissy slave domonique”

I would like to thank you for a great web site. When I first found it, well it was like receiving a gift. I wish you had been around when I was younger.

Thank You for accepting my application and allowing me the privilege of entering the interior of Your site. It has indeed had a profound effect on my psyche. i view myself as transgendered, and i have been progressing along the… Read more “jamie”

The House of Sissify is absolutely the best sissy site on the web. This sissy has learned so much since joining. The advice and support are wonderful. s.he has learned how to love, honor, obey, and worship Superiors and… Read more “stephanie kimberlie prince”

This sissy has just finished he.r second month with House of Sissify! I am amazed at how friendly and helpful everyone has been to this new sissy! Jamie is on chat almost every day for an hour or so catching… Read more “jamie”

I wanted to thank you for the insight into TransGendered Persons. As a Psych student doing a thesis on Gender Issues In Counseling your information helped to clarify and reify my own position with regard to gender identification psychology. I wish… Read more “Todd”