Holiday Preparation

Beep beep.

For the third time that day my wife was texting me. “You haven’t forgotten your appointment with Laura have you?”

As if I could forget it. Since my experience in the department store on the Saturday I’d thought of little else. We’d been getting things ready for our summer vacation when my wife had decided that my comfortable but admittedly old swimming trunks no longer fit the bill. Hence I found myself in her favourite department store getting fitted for new swimwear. That would have been fine, except that my wife took me to her own personal shopper, Laura, who was of course based in the ladieswear section. Laura didn’t seem to think that was an issue at all, she led me off into the ladies’ changing area and proceeded to measure me up for a new costume whilst one of her assistants, Ginny helped my wife find something more in vogue.

To ensure she got an accurate measurement of my size Laura stripped me not only to my underwear but completely naked and left me in the changing cubical while she took my clothes for safeguarding behind the counter. That left me at the mercy of a couple of ladies who had been trying clothes on in the changing area, resulting in me getting very aroused. Then when my wife and Ginny returned with some costumes to try on Ginny had gained confidence as I tried on first one then the other pair of trunks. But not before I’d completely embarrassed myself by ejaculating almost into Ginny’s face following which she finished by sucking me clean.

Finally, before we left, Laura had then discussed the shabby state of my equally old boxers with my wife and the pair of them had agreed that I needed a full set of replacements. Since then I’d been dreading my return to the store tonight after work. How could I face Laura again? And worse, how could I face Ginny? Had they talked about me to each other? Of course they must have done. Who wouldn’t?

So that’s how I ended up returning to the store after work on Monday. Nervous, embarrassed and a little afraid of what the evening had in store for me, or at least what Laura might have in store for me. I walked up to the ladieswear department slowly, trying to delay the inevitable. Laura spotted me approaching and came over to greet me.

“So good to see you again, Dani.” She embraced me, her arms instantly wrapped around me, her hands on my butt pulling me in towards her chest. Her full breasts squashed in the process but I was more aware of her hands than her boobs. She gave my bum another squeeze and then stepped back, before taking me by the hand as we walked. The short redhead started talking.

“I’m afraid I can’t look after you myself today, Dani. Now don’t worry, I’ve talked to some of the other staff about what you need and Kerry and Ginny, you remember Ginny right?” How could I forget Ginny? “Well, Kerry and Ginny have volunteered to help you with new underwear. Kerry works in the lingerie team so she knows everything about underwear, let’s introduce you.” She spoke as fast as we walked and I realised we were already in the lingerie half of the floor. What Laura thought the benefit of knowing about lingerie was for me getting new boxers I hadn’t quite grasped but I saw Ginny who then waved at me and another girl about Ginny’s age walk over to greet us.

“Hi Dani,” Ginny smiled

“This is Kerry,” Laura made the introductions, then excused herself. “I’ll leave you in their capable hands, Dani. If you get really stuck, girls, then give me a call, but I’m sure you’ll be fine. Dani’s no trouble at all, are you dear?”

Ginny took my hand next and Kerry walked on my other side as Ginny guided me into another ladies’ changing area. This one was a little different. One wall was a ceiling to floor mirror whilst opposite were a number of changing cubicles that seemed enormous compared to the tight space I’d been in before. The middle of the room was open with a few chairs at one end. Ginny guided us all into one of the curtained off cubicles before Kerry finally spoke.

“He’s a bit older than I expected, Ginny,” she whispered.

“Oh don’t worry about that, Kes, he’s ok. And he tastes delicious, don’t you, Dani?” My face reddened immediately, as if cumming into Ginny’s face on Saturday hadn’t been bad enough, now she was admitting it to another twenty year old girl. “Awe are you feeling shy today, Dani?” Ginny continued her banter. “Right let’s see what we have to work with. Can you kick your shoes off please, Dani?” Casually Ginny began to unbutton my shirt. “Give us a hand, Kes.” I jumped at the touch of two pairs of hands working on removing my shirt. That’s when I noticed the curtains of the cubicle hadn’t been pulled across after we walked in.

“Um, Ginny,” I began, “don’t you want to pull the curtains?” I asked timidly.

Ginny looked across at the wide opening.

“Nah, not really, it’s only us in here and besides, Kes and I need to have a clear view of any other customers arriving.”

She didn’t seem worried by the fact that anyone walking into the changing area would also have a clear view of me.

“But what if they see me, Ginny?”

“Stop worrying, Dani. I’m sure they’ll understand and wait their turn.” That wasn’t what I meant of course, but it seemed pointless in pursuing the conversation. The girls already had my shirt off and were working on my trousers. Ginny expertly undid my belt, button and zipper before Kerry, standing behind me, pulled them down to my ankles.

Ginny gave me a slight tug forward and as I stepped towards her Kerry slipped my feet out of my pants. If it hadn’t been for Ginny holding my hands I’d probably have fallen flat on my face.

“Ooh, socks.” Ginny giggled.

“What?” I was confused, of course I was wearing socks.

“Horrible look, Dani. Us girls don’t like to see a guy in socks.” I felt Kerry’s hands around my ankles and one at time she lifted my feet up and removed my socks.

“That’s better, now let’s have a look at you.” Ginny let go of my hands and both girls stepped away from me to get a better view. I stood in my old faded boxer shorts, my back to the changing area as they both stared at me.

“What do you think, Kes?” Ginny asked her friend.

“Grubby aren’t they?”

“Yeah, definitely time he had new ones. Think you can come up with something?”

“Probably, I’ll have to get some measurements though.” She slipped a tape measure out of her pocket and stepped back towards me.

“Um, don’t you have my measurements from last week already?” I thought I’d be helpful.

“Don’t worry, Dani, Kes is a professional. The ones I took last week were fine for general things but Kes is a stickler for detail. I’ll leave you with her for a moment, just need to check there’s no one waiting.” What? Where was she going? She left though, leaving me in the cubicle alone with Kes who simply smiled and unravelled her tape measure.

“Now, Dani, I’ll need you to keep completely still while I get your measurements sorted. Can you do that for me?” she almost cooed as she stood a few inches in front of me. At a head shorter than me she looked up into my face, her glossy red lips gently parted as she finished speaking. I nodded, finding it difficult to find words as I stood in front of this young girl, only wearing my underwear.

“Good, Dani. Just stand like that a moment and I’ll start.” She reached her hands around me and passed her tape around my waist. Our bodies touched as she stretched to complete the manouever. Her breasts pressed against my chest and I felt her short skirt against my thighs. The touch was over quickly as Kes dropped to kneel in front of me as she lowered her hands to my waist. Her head now level with my groin I felt her soft fingers flutter over my skin as she calculated my waist measurement. Her hands were cold and I shivered as they rubbed against me.

“Sorry, my hands are cold aren’t they.”

“A little yes.”

“They’ll soon warm up.” I looked down at her to try and understand what she meant, but could only see the top of her head as she concentrated on her tape.

“Good, Dani. Now your hips.” Her hands changed location and again she leaned further in to reach her hands behind me as she repositioned the tape. Now her face was buried in my groin, I could feel her nose pressed against my soft cock, that I knew wasn’t going to stay soft for long if this continued. This time Kes took longer, her hands fiddled behind my bum, her face still squashed into my front. I felt my cock twitch at the continued pressure and groaned inwardly. Please no, don’t let me get an erection now. I squirmed.

“Keep still, Dani,” Kes’ muffled voice rose from my underwear. Then she pulled back to speak more clearly.

“Sorry, Dani, It’s difficult to work out where your hips are.” She put her tape on the floor between my bare feet. Then swiftly, she put the palms of her hands on my waist. Slowly she slid them down until they rested on my slight hips.

“Hmm, you’re so skinny,” she giggled. Then she took hold of the waistband of my boxers. I thought she was going to pull them off like Ginny had done before. Instead she began to roll them down. Slowly, Kes curled them over and over until they passed my hips. She stopped when my hip bones were visible, my underwear rested half way down my bum cheeks, the fleshy tops of which were now exposed. It was the same at the front, my bushy pubic hair was clearly in view as Kes picked up her tape and leaned in to pass it around my half exposed arse.

Her still cold fingers caressed the top of each cheek as she fished for the end of the tape, I felt one hand slide inside my rolled up underwear and then give my bum a cheeky squeeze. Of course, her face was again buried into my groin as she stretched her arms around me. Now I could feel her warm breath as it wafted across my pubic hair. My cock twitched again, this time lifting slightly and pressing against Kes’ chin. She must have felt it move as she stopped and then pressed her chin down against my now stiffening member. This was going to end only one way I thought as my cock reacted again. Again she pushed back, now her hands grabbed my arse as she forced her face harder into my groin. In seconds I was semi-hard, my cock tenting my old, tired boxers. Now Kes pulled the tape around to the front, positioned over my hips. She rocked back on her feet as her hands came to together in my nest of hair. She studied the tape as her fingers moved it into position, pressing as they did into the base of my cock my erection continued to harden. My tent now pointed straight towards her. She just nudged it downwards out of her way though, seemingly unconscious of what she was touching.

That’s when I heard noises behind me in the changing area, indistinct voices, ladies’ voices of course. I made to turn round and see but Kes immediately commanded me to be still.

“Don’t move, Dani. I haven’t finished yet. Just stand facing forwards please.”

I did as told but was sure the female voices were now giggles as I stared ahead of me towards the back of the cubicle. I just hoped that Ginny had pulled the curtain across when she left. Surely she had, right?

“That’s better, Dani.” Kes’ voice rose from below me. “Now, I just need an inseam measure, can you move your feet apart please?” I shuffled my feet slightly in response.

“A bit further.” I felt Kes’ hands on my ankles as she guided my feet to where she wanted them, more than shoulder width apart.

“Perfect.” Kes’ hands slid up my thighs, they reached the bottom of my boxer short legs but did not stop until she had a hand up each. I could feel her cool fingers against my balls as she passed the end of the tape from one hand to the other. She held the tape with one hand under my balls, almost against my bum hole I thought, whilst the other hand then descended my thigh, unravelling the tape as it went. I was fully aroused now, the rolled down boxers preventing me from pointing straight up. Kes’ hand moved against my balls as she made sure the end of her tape was where she wanted it. Eventually she finished, the tape fell to the floor whilst Kes let her fingers linger inside my boxers longer than was necessary.

She rocked back onto her heels and looked up at me, my tent poking right at her. She reached out and wrapped her hand around my erection and tugged it down, still encased in my underwear.

“This has a real habit of getting in the way,” she laughed as she gave it another tug. “It’s going to be interesting keeping it under control. Right I’m going to get some samples for you to try on. Stay there.” As if I was going to wander off anywhere in my underwear and with a hard-on.

Kes stood up and walked out of the cubicle, I turned as she passed me. Shit! The curtain had been wide open all this time, Ginny had set me up big time. I thought at least Kes would close it as she left, but no, she didn’t even seem to notice. I froze, almost naked and erect I couldn’t turn round completely. Instead I peered over my shoulder to watch her disappear. I scanned the changing area behind me but most of my view was obscured and I didn’t want to move closer to the cubicle entrance for fear of being seen. It was clear though, that I wasn’t alone, I could just make out a pair of high heels attached to two slender, stockinged legs. Someone was sat in the changing area. Startled, I shuffled deeper into my changing cubicle, hoping that Kes or indeed Ginny might return soon and at least close the curtains. I felt far too exposed to move close enough to pull them across myself. The only good thing about being left alone was that without Kes’s fingers all over it my erection was beginning to subside.

In fact I didn’t have too long to wait before Kes returned with a bundle of what turned out to be underwear.

“Here we go, Dani, I’ve brought in a few things to try on to get the size right.” She started to lay out the underwear on a chair in the corner of the cubicle. That’s when I took notice of what she’d brought.

“Er, Kes, aren’t they all female panties?”

“Yeah, this is the lingerie department, right.”

“I know, but I’m not here to buy ladies knickers.”

“Oh I know that, silly. It’s just to make sure we get your size right. Once I know which of these suit you best then I can convert that easily into menswear. Sorry, but it’s easier for me, I only dress women. Right get those horrible old things off and let’s start with these.” Kes held up a dark pair of cotton briefs.

I gulped and hesitated.

“Come on don’t be shy.”

“Can you at least close the curtain. Please!”

“What? Oh ok, sorry it’s usually only women in here, I forgot.”

Kes walked over to the cubicle curtain and finally closed it.

“Better?” I nodded.

“Good, now will you finally get rid of those grotty underwear.” Slowly I moved my hands to my hips where the rolled up tops of my boxers still rested.

“Hurry, up or I’ll pull them off myself,” Kes encouraged me.

With no option left I peeled them down my legs and stepped out of them, my hands instinctively covering my genitals as I stood back up. My cock remained soft but I wasn’t sure how long that was going to last now I was fully exposed to Kerry’s gaze. She noticed the change immediately.

“Oh good, it’s gone down. Don’t move, I need a measurement.” What! But there was nothing I could do. Kes took out her tape once again and kneeled on the floor between my legs. In seconds she had her hands at the top of my thigh and pushed my hands away from my genitals.

“Now don’t you go getting excited again yet, I need to know how long you are like this so I know how much room you need in your knickers for it to hang.” I swallowed deeply as she began to move my cock around, her fingers tickled my balls as she worked her tape into place.

“There, got it. Now all I need is a measurement once it’s fully grown.” She looked up at me and smiled. Her red lipstick still glistened as she winked at me.

“But there’s no hurry,” she continued, “in the meantime let’s try these on.” She reached over to the chair and again picked up the dark briefs. I looked at them and took them out of her hands. They were thin cotton briefs, not unlike some I had at home. Except for the lace edging that made them most definitely girl’s wear. Still better to wear them than nothing so I slipped my feet into them and pulled them up. I’m a skinny guy so actually they fit fairly well, albeit the legs had a higher cut than I was used to, apart from the lace trim and the fact that the material was so thin they weren’t that bad I thought. Kes seemed to agree.

“Not bad, Dani.” She walked around me and looked from various angles. “Let’s see you walk in them.” She dragged open the curtain and beckoned me out into the main changing area.

“You can’t be serious,” I began but Kes took hold of my arm and walked me out towards the wide wall of mirrors on the opposite side.

“WooHoo,” a voice called from the right as I stepped across the room. It was the woman whose high heels I’d glimpsed, in her mid-thirties she sat on one of the many comfy chairs. “What have we here?” she added.

“Oh this is Dani, I was just fitting him for some underwear,” Kes responded as another woman’s voice called out of a cubicle a few curtains further on from mine.

“Is that you, Sam?” she asked, obviously directing her question to the blonde woman in the heels.

“Yeah, Jacqui, it’s fine. We have a guy in here though so you better cover up.”

“A guy? What the..”

“Nah it’s fine, he’s wearing less than you I suspect.” At this a redhead poked her head out of the cubicle and stared at me.

“Oh my. Whoah how cute.”

“Dani,” Kes broke in, “can you walk around for me please? I want to see how well they hold.” Kes got me to walk around the open space as she and the two women watched. Eventually she stopped me.

“Actually they are better than I expected for a first attempt,” she mused. “I think maybe you need something fuller at the back,” her hand caressed my bum cheeks as she spoke. “They cut across your cheeks a little,” she continued her fondling. “Would you like something fuller or are you happy like that?”

“He should try a g-string,” Sam proclaimed to Jacqui’s amusement.

“Oh, I don’t think that would work,” Kes began seriously. “A g-string wouldn’t offer much support in the front.” At this she began to fiddle with the panties. The legs were highly elastic so had formed a natural pouch for my bits to sit in. She slid a finger under the elastic and stroked my balls.

“Hmm, maybe you need a little more room in there though.” Kes dragged me back to my cubicle and rooted through the pile of underwear she’d brought in.

“Here, give these a try.” I turned to check that the curtain was closed but was shocked to see both Jacqui and Sam standing there. Jacqui I quickly noticed was only in her bra and jeans, she’d raced from her own cubicle so fast that she hadn’t finished dressing. Sam just stood there in her little black dress and heels.

“Can’t wait to see you in those,” Sam announced as Kes thrust a pair of panties into my hand.

“Come along, Dani,” Kes encouraged me, “here let me help and she knelt in front of me grasping hold of the waistband of the little briefs. My hands were full holding the new panties she’d given me and before I could do anything she’d pulled the briefs to my ankles. Behind me I heard both women gasp as my bare bum came into view.

“Step out of them, Dani,” Kes continued to undress me. There I was completely naked surrounded by three women. I held the panties I’d been given in front of me, even though Kes had already seen everything and had her hands on me.

“Nice butt,” one of the women behind called out.

“Yeah, so firm and round,” giggles of laughter.

“You’d die to have a butt like that wouldn’t you, Sam?”

Kes pulled the new panties out of my hands and opened them up for me to step into. My cock bobbed in front of her face as she knelt on the floor in front of me. I lifted one foot up for her to slip the panties over it.