We started Saturday with another failed attempt at lovemaking. Within about 30 seconds of Beth playing with my penis, I gave in and came. I wasn't even erect, but just the sight of my beautiful, stunning girlfriend playing with me was enough to tip me over the edge.
Once again, like last night, there was no evident frustration from Beth. Only embarrassment from me. In fact, she seemed amused.
"Aw. Such a pretty penis!” Beth remarked, grinning and playing with it in its flaccid state. "It's perfectly formed in every way, only slightly... petite."
"Petite! What do you mean? You've never said anything before!"
She just carried on stroking it and diffused my irritation completely with another smile. Beth could do that to me.
"Don't be so sensitive baby! I don't mind. In fact, I love your penis. It's cute, and much less threatening than other men's. In fact, your penis is the cutest little penis in the whole wide world! Just perfect!"
There wasn't much I could say to that. I always knew I was smaller than average. I guess I should be grateful that Beth liked it so much.
We ate breakfast in our dressing gowns, then headed upstairs for my first lesson.
"Right then my gorgeous little thing. Lesson number one, and the first thing you'll need to know to help Amy out. Why do women wear dresses?”
"I don't know. Er…to look hot?"
"Well, sort of. Sometimes. We know we look hot in the right dress, but it goes deeper than that.”
“In what way?”
“Well, firstly, all women are different, and there are lots of different occasions when we choose to wear a dress. You have to remember, we've been wearing dresses since we were little girls, and constantly been receiving attention and compliments for wearing them. 'Doesn't she look pretty', and that sort of thing.”
I knew what Beth was talking about. My sisters would always get compliments growing up about their outfits. I never did.
Beth continued. "Take me, for instance. There are a few reasons I love to wear a dress. One, to look pretty. Dresses ARE pretty. They flatter my shape, emphasise my chest if I want, skirt over my hips, and show off my legs. They come in pretty colours and shapes. They appeal…well I guess to the deepest essence of my femininity. There is nothing like wearing a very pretty dress to make me FEEL pretty."
I was thinking that Beth didn’t need to wear a dress to look pretty.
"Secondly, because they're beautiful. Dresses can be like…a work of art. And wearing the right dress makes me feel special. Sort of like a wonderful diamond ring. Except prettier! Thirdly? Because dresses feel nice to wear. And they’re simple. There's nothing simpler than slipping on a cute sundress on a hot day. Cool, simple, and the pretty bodice and flowing skirt against my legs feel amazing."
I loved hearing Beth talk about this. It’s why she’s such a hit at work. She’s passionate about fashion.
"Four. To feel like a woman. Wearing a gorgeous dress and being held by a big, strapping man makes me feel, well, like more of a woman. As if it accentuates the difference between my man and me. I feel more feminine in a dress. The same goes for skirts."
I gulped, wondering if she felt just as feminine being held by me. I was hardly her big, strapping man. Is that what she wants?
"Five. To impress other women. We are competitive, and we want to be the most attractive girl at the party, or in the office. Which often means wearing a dress no one else has, and looking fabulous in it. There are five reasons for starters. And they're just some of my reasons. Every girl will have her own.”
“Why is that important?” I asked.
“So you are listening! Well, when you're providing the kind of personal advisory service that Amy needs you to provide, it's important to consider how a girl is going to feel in a dress. Why she wants it. What her goal is. Got it?"
"I think so."
"Don't worry honey. The more time you spend in a dress shop with other women, the more you'll understand."
Other women? Did I hear her right?
Beth then proceeded to take me through a descriptive tour of different dress types, using examples from her walk-in wardrobe. She wore each dress as she went. Beth was clearly having a great time showing them off…
Sheath dress. Skater style. Baby doll. Empire line. Shift dress. Tea length. Cocktail. Sundress. Knee length. Above the knee. Below the knee. Mini dress. Wrap dress. Bodycon dress. Slip dress. Halter-neck.
Then different types of skirts…
Pencil. A-line. Ballet skirt. Mini skirt. Pleated skirt. Wrap skirt. Tulip skirt. Tennis skirt. Fishtail skirt. Peasant skirt. Ruffle skirt…
Different materials too, and the way they draped against her legs.
"Amy will brief you on which skirts or dresses suits particular body types."
"I'll look forward to it."
"Okay", Beth laughed. "Don't get sarcastic. Now let's have some fun and see if you've been listening. A test. Remember, you'll have to empathise with every single customer. Quality of service and advice is a key differentiator of Amy's business. Take your dressing gown off."
"But Beth, I'm naked underneath. And I am NOT wearing any of that stuff."
"Don't be silly! I'm not asking you to wear anything. It's just a test, and you can't do it in your dressing gown. Take it off."
"Ok." I removed my dressing gown. Beth was still wearing the last dress she tried on, a pretty pink and white lacy knee length number. The dress was cute, and she made it cuter.
"Now close your eyes. I'm going to hold a dress against you, and by it's length, touch and shape, you guess what type of dress it is."
"But this is silly."
"Humour me. It'll help you instinctively know the dress styles without having to think. Now close your eyes."
Beth stood in front of me, and pressed the shoulder straps of the first dress up against the shoulders of my naked body. I immediately felt the skirt of the dress tickle my upper thighs, and innocently flirt with my penis. It almost felt like I was wearing it. It felt... sort of...good. It’s fair to say that in that moment I started to get scared.
"Beth, this is stupid."
"Don't be silly Rich. I promise you this will help. Trust me. Now keep your eyes closed. Ok. What type of dress is it?"
"I don't know. Can I touch it?"
"Of course baby. Touch away."
I felt the dress. As I did so I pressed the light material up against the front of my body. I moved my hands down, over my hips and along the length of the short skirt. In the deepest, most private recesses of my mind, I couldn't help imagining I was wearing it.
"It's a baby doll dress."
"How do you know?" Beth asked.
I had to think hard. "Because…I can feel the skirt end around the mid thigh area, and where the waist nips in is…higher than usual."
"Well done! You're a natural! And how do you feel, wearing it?"
"Sorry? Say again? I'm not wearing it!"
"Let me rephrase. How do you think a girl feels, wearing this dress?"
"Er...exposed... flirtatious... sexy... feminine."
"Possibly. Very good! Next one"
Beth took the dress away from my body, and immediately noticed that I was semi-erect. Initially she looked shocked. Then, saying nothing, just smiling, she handed me a pair of panties that suspiciously came immediately to hand.
"Put these on."
"What? I can't wear those. They're ... they're your panties."
"Oh don't be a prude. I can't have you making a mess on my dresses, and I can tell you're turned on. These panties were just near me. Anyway, it wouldn't work using your underwear. Remember, I said that you needed to empathise? This will help."
By now my face was beetroot red. This was the first time I'd remained in any way erect for any reasonable length of time in Beth’s presence, it was because of a dress.
"It's okay. I get it, so don't be embarrassed", Beth said. "The dress material feels nice against your skin. Especially the soft skirt. I know what that's like, remember. It can be quite nice. I feel it too, sometimes. Now slip on those panties, and let's do the next dress."
Beth handed me the panties. I pulled them up my legs, the very first pair of panties I'd ever worn. They were made of black lace, with a small bow in the front. The material felt so soft and feminine over my crotch. Beth stifled a laugh as I tucked my penis in. Despite my half erection, the material still covered my whole penis, which didn't even reach halfway to my belly button even when it was hard.
"Right my pretty little cherub. Next dress. Close your eyes."
This time Beth moved around behind me. She stood directly up against my back. The folds of the skirt of her soft lace dress were already lapping up against the backs of my legs. Her breasts were pressing into me too.
Then she reached around the front, and pinned the straps of the next dress up against my shoulders.
"Hold the straps here babe", Beth asked. I complied, pinning the straps to my shoulders with my fingertips. Beth then moved her hands down my body to hold the waist of the dress against me around the side of each hip.
With my eyes closed, and the combination of Beth's dress against my back, allied to a similarly long dress pinned up against my front, it TOTALLY felt like I was wearing a dress.
"Ok. Before you guess what type of dress it is, tell me how you feel."
"I ... I ..."
"Come on honey. You need to learn to empathise with Amy's customers. How do you think a girl feels wearing this dress?"
"I... d...d...don't know."
Beth knew I was struggling. The combination of the panties, Beth's dress and body against my back, and the dress at my front...it was all too much.
Beth now whispered words gently in my ear. She pressed her body against mine again.
"Feminine? Romantic? Girly? Smart? Pretty? Sexy? Desired? Adored? Wanted?"
Her left hand moved around to the front of my body, brushing lightly, once, twice, against my penis through the skirt of the dress and panties.
I came immediately.
Beth stepped back and looked shocked. She was clearly lost for words, despite the fact she’d known I was aroused. I just stood there, mortified, both hands over my crotch and the mess in my panties.
"Beth. I'm sorry. I don't know what happened..."
She just stared at me, looking horrified at first. Then the corners of her lips crept into a smile.
"Don't worry honey. But we definitely need to change those panties."
I moved into the adjacent bathroom, took the panties off and washed myself. As I walked back into the walk-in wardrobe, Beth was already holding another pair of her panties, with a huge grin on her face. I’m sure she was stifling laughter.
"Put these on. That's not likely to happen again soon, so I think my panties are safe!"
We spent the next two hours going through the remainder of the dresses and skirts. By the time we'd finished, I'd guessed 90% correctly, and had gone through three more pairs of Beth's panties.
THE PHONE CALL
After lessons, Saturday passed without further incident. Come Sunday, following yesterday's 'hard work', I woke up still feeling tired.
Why was I turned on by having skirts and dresses held up against me by Beth? Why did Beth's panties have such an effect? And how come Beth was taking it all in her stride?
I didn’t understand.
It was late morning, and we were still in bed. Beth was snuggled up against me in her sexy nightie, absentmindedly stroking my penis while talking.
"You did really well yesterday babe. Apart from making a mess in my panties, you dirty little kitten!" Beth was chuckling to herself. "I need to call Amy later, update her on how far we got with the lessons".
"You're not going to tell her about...?"
"Relax my darling boy. I'll only tell her what she needs to know."
I went downstairs to prepare Sunday brunch, with Beth's favourite foods of omelette and smoked salmon. We had a nice leisurely meal, and Beth left the kitchen to call Amy.
For some reason, about five minutes into the call, I got really nervous about it. What if Beth DID tell Amy what had happened? That would be SO embarrassing on my first day of work.
Beth was talking on the landline upstairs. I went upstairs to the bedroom, pressed the mute button and picked up the receiver.
"...Be just like old times Amy. I'm so excited about coming to model dresses again. It'll be fun swishing around in your clothes for a few evenings. Are you going to model some too? I mean, you've still got the looks girly..."
"Perhaps Beth, perhaps. Although it seems a bit self-serving to be designing, selling and modelling the clothes myself. Know what I mean?"
"I guess. But we'll have so much fun. And now Rich is helping you out with the selling, perhaps you'll have more time for other things."
"I hope so. It would be fun to model dresses again, especially with you. Maybe we can get some hunky male models in too. Remember Josh? The guy you dated? Wasn't he your first love?"
My interest peaked, and morale bottomed out, at this point. I'd never met or heard of Josh before. How would Beth respond?
"Yes. Of course I remember Josh. He was wonderful. One of the few guys I've ever met who was sensitive, caring and had a hot, ripped body. They're so hard to come by Amy."
"Tell me about it. I remember what you used to say about Josh's huge…you know...wasn't he your first?"
Beth wouldn't care about that. Surely...
"Oh god yes. I remember the first time I saw it. I almost had kittens. Fair play though - he sure knew how to use it. There's definitely a part of me that misses those days."
Beth sounded wistful. I was just upset. I knew Beth had boyfriends before me, and many of them. I mean, she's stunning, so it makes sense. But I had no idea she missed one of them so much! And she missed his huge penis...
Beth continued, "It's a shame he moved out to LA. I heard his modelling career really lifted off."
"Maybe I could book him!” Amy chuckled in response. "Seriously though. If things carry on taking off at the shop, soon I'll need a handsome, rugged male model. To sort of offset the femininity of the dresses. Play to women's aspirations. You know...get the dress, get the attention of your perfect alpha male."
"Oh Amy you are silly sometimes. It would be nice to see Josh again though."
What! Would be nice to see super-sized penis Josh?
Although if that was such an awful thought (and it really was), why was I now erect?
Amy replied, "Speaking of alpha males, how's Rich doing."
"Ha ha Amy. You are a tease. Rich is doing really well. I really think he's going to be a big hit at the shop. And if that works out, hopefully the freelancing work will follow."
"How did the lessons go?” Amy asked.
"Well. I don't know what to say."
"What do you mean?"
"Something strange happened. Firstly, you have nothing to worry about. He knows all of the dress and skirt styles not just by sight, but also by touch. So I think he'll get off to a really good start."
Beth suddenly starting talking in a half-whispering voice.
"But you know the problems I told you about? The ones Rich has been having?"
"You mean the erection and, ahem...premature problems?” Amy asked.
"Yes. Well I thought they were just down to the stress of not having a job. And I know how stressful that must be. So I totally understood. I mean, I think I'm the only one from our degree course that has found work. And that was through my old dress modelling contacts. The other girls on the course are all pretty stressed."
"Go on", said Amy, sounding very interested now.
"But when I did the lessons yesterday, as I was testing him on the very first dress… Do you remember the lilac baby doll dress I wore when we were on holiday?"
"I remember", said Amy. "The silk one. It's gorgeous. You got so much male attention in that dress! I bought the pink version when we came back."
"That's the one. Well, I held it up against Rich naked, and..."
"You did what?"
"Silly I know. But I really want Rich to be ready to work at your shop. I wanted him to learn the dress styles from touch, and learn to empathise with the girls buying each style. That way he'd be able to give better advice to your customers."
"I appreciate the thought. But he agreed? What kind of man...? Never mind. What happened?"
"Well", Beth said, sounding a bit embarrassed. "I don't know how to say this...but he got...well... hard. He got erect when the dress material touched his body."
Amy started to laugh. Beth started laughing too. "What did you do next?" asked Amy.
"The only thing I could think of was 'don't make a mess over my dresses!' So I quickly grabbed a pair of my panties. I wasn't thinking, and we were in the walk-in wardrobe...they were right next to me."
"Don't tell me he put them on? Surely no man would agree to that?"
"Well, that's part of what's worrying me. He put up a tiny bit of a fight, sort of a token effort. And then he slid them on compliantly. But then I put the next dress up against him, and he... well he must have liked it, because he actually...you know...came!"
There were shrieks of laughter from Amy at the other end of the line. I couldn't believe Beth was telling Amy this. It felt like a huge betrayal of trust. But at the same time, Amy and Beth are such old friends, and Beth was worried about something...why shouldn't she discuss it with Amy? The problem is, from tomorrow, Amy is my boss!!
The conversation continued.
"You don't think he's gay do you? I mean, he was obviously aroused by wearing your panties. And having the dress up against him. Maybe he was thinking about wearing the dress. And panties, bra, heels...everything. Plus he was the only guy on your course, he struggles to get an erection for you, and you're stunning. AND he's hardly the most...well…masculine of men is he. How tall is he again?"
"My height", Beth replied. "5ft 7."
"And he's thin. I remember you telling me."
"He's thin because he used to swim lots. He can't help it that he's, well, small, for a man. And it's still totally possible that his erection problems are because he's out of work. It's not good for his libido. Plus, I knew him for years before we got together. He's sweet, caring, attractive and good company. And he's never shown any interest, or been involved, with any guys."
"And he wore your panties and gets turned on by contact with your skirts and dresses. Definitely not gay", replied Amy sarcastically.
"Yes. There is that", Beth admitted.
"So if he's not gay, what is he?"
"I don't know. It's probably nothing. But I'd like to find out more. I love him, so I need to know. Besides, despite what happened, I sort of...I don't know...liked the events of yesterday. Watching it made me feel...powerful. They were my clothes getting him into that state. It might be sort of fun to get to the bottom of it all."
"I agree. It could be fun. And I sort of get the 'power' thing too. I've never met a guy who's so easily persuaded to do those sorts of things. What man would agree to that? Anyway, I'm looking forward to meeting him tomorrow. Even more than before!"
With that I hung up. There was no way I could tell Beth that I'd been listening to her call. At the same time, I had to work for Amy the next day, and she knew EXACTLY what had happened. The panties. The dresses and skirts. Everything.
The thought that Beth and Amy were planning on having fun with this...that filled me with dread more than anything.
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