Ann Ch. 02

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Ann's first date.
21.6k words
4.81
9.4k
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Part 2 of the 8 part series

Updated 04/26/2024
Created 01/12/2024
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shecret
shecret
64 Followers

I woke up and had to pee. I remembered that I was in Jenny's bed and she was lying next to me. Carefully, I lifted my head to see the alarm clock on her bedstand. It was 04:50. I used to wake up early to help Dad on the farm, but since I left home, I often slept until the alarm clock woke me up at 7.

Jenny was asleep, and I moved very slowly, so I didn't wake her up. I got clear of the sheets and turned my head to watch where I put my feet on the floor. I hadn't moved much before I was stuck. My nipple was stuck to something. I looked down in surprise and found that it was held between a thumb and an index finger. I followed the hand and arm with my eyes and ended up looking into Jenny's eyes.

"Where do you think you are going?"

"I ... I was going to the bathroom. I need to pee."

Her face changed expression from strict to kind. I was a little confused.

"Oh, I thought that you were going to sneak out on me." She released her grip on my nipple.

"I'd never do that. Never ever!"

I bent over and kissed her forehead. She raised her head for a real kiss and let me go.

In the bathroom, I saw that my clothes lay on the bathroom floor and were still soaking wet. When I had peed, I hung them up on the rod for the shower curtain, they were dripping like they came from a bucket of water. Strange. I tried to wring them a little to get the water out, and I hoped that they would be dry in the morning.

Jenny was still awake when I returned to the bed, and after a long hug and a kiss equally long, we went to sleep again.

Jenny's phone woke us up at 6:45. Jenny had to be at the hospital later that morning. We cuddled a little before we left the bed for a morning bath. I was the first in the bathroom and saw that my clothes had fallen on the floor again, dripping wet. I put them aside and adjusted the shower to a good temperature. Jenny joined me and we washed each other. We kissed a lot too. I kissed her breasts and went south on her, but found out that all the stories I had read about pussy licking in the shower must be fakes. I couldn't breathe - my mouth and nose got full of water. I coughed and rose.

"Lesson learned. Why do they write that shit in the stories?"

Jenny laughed.

"Welcome to the real world where showers are wet and farts happen. By the way - how are you today? No cold?"

"I think I have a sore throat."

"Oh no! "

She felt my glands on the sides of my neck. They felt normal to me.

"Stick your tongue out. Does it hurt?"

I did as I was told. And nodded.

"Push against my finger. And this way. And this."

It hurt a little no matter which way I pushed her finger with my tongue.

"Aha. It's a standard NLS."

"NLS? What is that?"

"New Lesbian Syndrome. You have used your tongue too much in ways you are not used to. Like being sore after a workout. There is no cure for that except no kisses and no oral sex in a month."

"WHAT?"

"Just kidding, hon. It will be over soon. The doctor's orders are coffee and ice cream. I intend to benefit from that tongue tonight. Don't worry. And it has no name - I just made it up."

We did not spend much time in the shower - Jenny had a deadline. We toweled each other and she rubbed the lotion in my shaven area. She took another towel and took care of my hair. It was nice to be pampered that way, and afterward, Jenny brushed my hair before she took care of her own.

I looked at my wet clothes.

"Don't bother with them. I've got something you can borrow."

She went to another room, equipped with two desks and a wall of closets, and returned with some clothes - a pair of blue jeans, a black T-shirt with some flower print, a pair of socks, and a thong. I had never worn a thong before!

I would not be able to fit any jeans of Jenny's. Perhaps Rosie had left something behind. I didn't dare to ask her, I thought that she would tell me when she was ready.

I fumbled with the thong - it was hard to tell which side was front or back, in or out, and where the legs had to go, but finally, I was certain that I had it right and stepped into them. It was a strange feeling when they slid home - a thin piece of fabric going deep in the crack of my ass. It was new to me, arousing and exciting. The jeans were tight as in t-i-g-h-t. I finally got them on and managed to close the button on the third attempt. Jenny had already dressed and hugged me. Then she slid her hands to my ass, squeezing each buttock.

"Mmm - fits quite ok! Here is a T-shirt, let's have breakfast."

She held the T-shirt for me - I just had to put my arms into the sleeves and she helped it over my head. It wasn't as tight as the jeans, and the flower print concealed the two bumps my nipples made. Then we went to the kitchen.

Jenny had started the coffeemaker while I was cursing my wet clothes, and the coffee was ready. We heated some buns from the freezer in the microwave oven. I saw what else her freezer held and I wasn't impressed: Some TV dinners, frozen pizzas, and bags of ready-made buns. I had suspected something like that since I had spotted their shopping cart at the supermarket.

"I am afraid that I am not a kitchen person."

Jenny looked a little embarrassed.

"That's ok - I eat buns in the morning too."

At least she had a decent cheese and jam in good quality.

"I have a few things to talk about. I believe your letter and took a chance with a health issue that I take very seriously. But to be sure, I'd like both of us to take an STD test. I have patients to take care of and I am sure that you'd like to know you are safe too."

"But of course! I had never thought of that. I could have done it in advance if I had known ..." Jenny waved me off.

"I am sure that everything is ok - if you haven't slept with anyone, you are most likely clean. But it is a principle of mine."

"Where can I get it? I have the day off and I just need to do a little shopping. You know - some clothes that a friend of mine wants me to wear on our date tonight."

Jenny found a notepad in a drawer and wrote a phone number and an address.

"Gee - you know the phone number to the STD clinic by heart? "

"You mean that I do this twice a week? No, it is the lab at my work. I call them almost daily. I'll tell them to sneak you into the queue and process your blood work today. I'll do the same when I meet at work this morning. Good, then this is dealt with."

"I am a little unsure what clothes to get. I am not shopping for clothes very much, and certainly not for a date."

"You can try here."

Jenny wrote a shop name and where I could find it.

"I want you to find something that you like. Skirt over the knee and nothing in black or some fancy fetish stuff you don't know if you like or not. Find something that you can wear at the summer party at work too. I can recommend this shop. Ask for Sofia and you will get the best help you can wish for."

"Thanks - I really appreciate your help."

I took the paper and pocketed it with some difficulties. I have never worn jeans so tight before.

"And by the way - I want you to wear those clothes until you need to change for our date; you'd better get used to tight jeans. When can you be here? Half past five? Then we have a long evening to get to know each other."

"That would be fine - I have plenty of time to get my things done. Half past five it is."

I poured us another cup of coffee. It was nice to have breakfast together, especially after a long evening of hot sex. I could easily be addicted to that.

We did some small talk until Jenny had to leave. I had my shoes and my house keys as my only possessions, the rest was borrowed. Jenny gave me the little tube of lotion for my skin and told me not to shave today. I put my phone number into her phone when she asked for it, and she sent me a message so I had her number.

Jenny got ready, and we left her apartment. We went down the stairs hand in hand, and before we opened the entrance door, we had a long hug and some kisses too. I couldn't believe that I was about to have a girlfriend. I didn't mind that I was entering (hopefully) a same-sex relationship; I felt it was a thing I had wanted for so long. It struck me that eventually, I had to tell friends and family, but that could wait, I wasn't in a hurry. As a first thing, I had to make sure that I really was the girl that she wanted. I couldn't fake anything, I just had to be observant, fast thinking, and play the game as well as I could.

"I don't expect you to chicken out, but if you do, please text me. A 'Sorry' will do."

"I won't chicken out. I am looking so much forward to our date. I have enjoyed last night very much and cannot thank you too much for your kindness. I like the way you have taken care of me."

We said our 'goodbye' and 'see you later' in the parking lot, and I headed home to get my phone and the keys to my bicycle. When I walked, I could feel the thong digging in my butt cleft. It sat all right over my pussy, but the general feeling of wearing a thong was completely new to me. Perhaps the tight jeans added to the feeling - it wasn't bad, just unfamiliar. And I felt like I was a little naughty.

At home, I got my phone and saw Jenny's message:

"Hi, Hon! What a night! See ya later today. Have fun."

I replied:

"I enjoyed your company so much. Thanks for everything - breakfast too. I am looking forward to seeing you again!"

I looked at the clock on my phone. It was a little early to go shopping - I guess the shops hadn't opened yet. I tried to memorize a shopping list: A skirt and a blouse. Perhaps a jacket, it was early spring and the evenings might be chilly. Oh, yes - I needed underwear. If I showed up in one of my plain white or skin-colored bras, Jenny would kick me out. And though I had a thong now, I thought that I wanted some panties of my own too - perhaps a bra set or two. I hoped I would be able to use bra set number two later this week, just as a little surprise. With such a short skirt, what about a pantyhose? No, stockings. I have never liked pantyhose and hadn't worn skirts for years for the same reason. And Jenny would not accept them, I was almost certain. I would have to ask in the shop about stockings. What was her name? Sofia, yes.

I added jeans to my list. I would try to find some similar to those I was wearing. I liked them. I realized that I needed shoes too. Suddenly, my long day off didn't seem that long at all.

The two mugs of coffee wanted to get out again, and I went to the toilet. As much as I struggled to get those jeans donned earlier, as much I struggled to get them off again. I just needed them down to my knees. I enjoyed pulling the thong down - it was much sexier than my own panties. I only had briefs - traditionally, boring and unsexy briefs in white. Well - some of them weren't completely white anymore, they used to be a very light grey after being washed a lot.

I managed to get my jeans up again after I had peed and got them buttoned on my second try. Then I made a call for the blood work, and they were very kind and asked me to go see them before ten o'clock.

I grabbed my rucksack. It is a practical bag for shopping when you go by bicycle. I really enjoyed riding my bicycle - the first couple of months I lived in this city, I always took the bus. My bicycle gave me more freedom and some exercise too. When my parents visited me this weekend, my mother mentioned that I had lost some weight again. It was good news to a girl who always had been a little on the chubby side.

I had all my belongings and got ready to leave. I looked at myself in the mirror and tried to look at my ass. As far as I could see, it was nice in those jeans. I was heading out shopping, looking sexy, for the first time.

Riding my bicycle in tight jeans was new to me too, because I was aware that everyone could see the real shape of my ass. I made myself a mantra, going 'Jenny wants me like this - it is ok, I like it.' I was hoping it would help me get the courage I needed. I watched the other girls in the street and realized that I was just dressed the same way as they were. It made me feel better, and I promised myself to be calm and try to act naturally. Of course, I had shopped for clothes before - now I just needed another kind of clothes.

I found the right place at the hospital quite easily. They were as kind as the girl on the phone, and they took five vials. I had thought that an STD test was just one tube, but they knew better. As I sat with the small cotton ball taped to my arm and pressing on it with two fingers, the nurse asked if I was ok with her taking a few swab samples as well. I was led to an examination seat behind a curtain and told to doff my jeans and panties. Each time I had to undress, I had fewer problems with the tight jeans, and I managed to get them off easier. The nurse returned and guided me on how to sit, and soon she had taken a few cervical swabs. She smiled at me and told me to dress again.

I left my phone number to get the results and thanked them. There wasn't any bill to pay - I guess it was because I was Jenny's new girlfriend. Sometimes it is a good thing to have friends.

The next stop was the shop that Jenny had recommended. I browsed the windows in the mall, just to get a hunch of what I was looking for. As I entered the shop, I was welcomed by a sales girl in her late twenties, I guess. Her name tag said 'Sofia'. How convenient - then I didn't have to ask for her.

"Can I help you?"

"Yes, I hope so. I have a date tonight and I need something to wear. I have thought of a skirt and a blouse, perhaps a jacket. And some underwear too."

"Do you know what style you are going for?"

"I saw the brown skirt in the window there. Do you have it a bit shorter? Like over the knee?"

"No, but I've got something similar. It is a little more pleated, let's look over here."

She showed me to the rack of short skirts, and we chose two different skirts I could try on.

"Let's find a blouse too, then you can try it all on together."

We looked for blouses, and she showed me different styles. I chose a few to try on, and Sofia suggested another one.

"The black trim makes it match black shoes if you go for such."

"I am not so sure. I wasn't supposed to be going for anything black."

"It will look fine on you, and she won't mind."

I stared at her until she made eye contact, and then I held her gaze.

"She?"

Her eyes widened.

"Oh, sorry. I just - I didn't - you see ... - All right, Jenny texted me that you would come."

She took her cell phone from her pocket, browsed for a few seconds, and held it out so I could read.

"I am sorry that I spilled the beans. Read yourself."

"Hi Sof! Ann needs a skirt and a blouse for our date tonight, perhaps more. I sent her your way. If she comes, help her find something not too kinky. I want it to be something she can use on other occasions too. Can I ask for a discount for her too? Jen."

"So, you know her?"

Sofia nodded.

"We are friends. Have you known her for long?"

"Not really. Our first real date is tonight. And it is my first date ever. I need some help."

"Let's find what you need, then you can try it all together. You mentioned underwear. You're probably going to wear a bra under this?"

I nodded.

"What size do you usually wear? Or are you going without like today?"

"No, I usually wear a 38C. My missing bra today is a long story."

Sofia looked at my bust.

"38C? Are you sure? Have you lost weight recently? "

"Yes, my mother noticed a weight loss this weekend. Salad and exercise."

She took a few black bras from a display and led me to the fitting room.

"Can I measure you without the T-shirt?"

"Sure."

We stepped inside and I doffed the T-shirt. I was comfortable with her. She was nice and knew her trade. But why are measuring tapes always cold?

"You are a 36D. A Big D! If you want, you can try a 38C, but try this first."

I put it on, and it sat better than my usual bras. Much better.

"There is a little push-up in this model. You'll need to adjust your puppies like this."

She showed me how, and I had never had a bra that sat better. I tried the blouses, and the one with the trim sat best and one of the skirts was perfect. We settled for the blouse in a cream color and the skirt in a medium brown color. She suggested a jacket, and we found one with room for my boobs.

"Are you going for stockings too? I have some good stay-ups in black."

"Yes, I guess that pantyhose is a no-go. I'll take them too."

"Let's try them on so you can see, what they look like."

I donned my first stay-ups the way Sofia instructed, and the top was covered all right by the skirt. I noticed that the hairs on my legs were visible through the stockings.

"I think that I need to shave my legs too. Those hairs are not pretty."

"Don't shave - wax! Or you will have bristles in a few days."

"Hmm, waxing. Isn't it something they do at beauty shops?"

"Yes. I can recommend a few."

She took a business card from a pocket and wrote two phone numbers.

"The first is both a hairdresser and a beauty shop. She's very popular and she's usually busy, but perhaps she's got a slot for you on short notice. The second one is a beauty shop I use from time to time. Try them as a second choice."

I thanked her and put her business card in my jeans pocket.

"By the way, since I have changed bra size, I think I need a few pairs. Have you got other models? And I need some panties too, perhaps like the thong I've got. Or does this bra come in a set?"

"It is not in a set. People prefer different types of panties. Those thongs come in packs of three. Or do you prefer something different?"

"No, thongs are fine. Or perhaps I should have some bikini style too. No, just thongs please"

I thought that I needed some more decent panties during work hours, but who would notice what kind of panties I was wearing? I decided that I wouldn't buy any standard briefs anymore. I could wear my old, white briefs during my periods.

"I'll get some for you. And I have a few bras for you to try on too."

I took the blouse off and put it back on the hanger while Sofia was away, and when she returned, I tried four or five different bras. I settled for two other bras. One plain for everyday use, and a daring shelf bra that just managed to cover most of my nipples, showing the top third of my areolas. In for a penny, in for a pound. I knew that it was against Jenny's directions, but I could afford it and wanted to surprise her one day. I told Sofia not to tell Jenny about it.

I dressed in my own borrowed clothes again, and Sofia folded my new clothes. I estimated how much I had to pay, but when she rang it up, it was much cheaper.

"Have you remembered everything? I think it should be more."

"No, I have given you a discount. It is not everything I can sell cheaper, and my friends know that. But the bras are 'buy three, pay for two'."

"Well thanks a lot! It was nice of you, and I am glad for your help with the sizing. Can you recommend a shoe shop? I need some jeans too, I think. These are borrowed."

"A real make-over? Wow! The jeans are from the shop over there in the next aisle, I guess. Try the shoe shop next to it. Have you worn heels before?"

"Yes and no. I have a one-inch heel on some of my boots back home, but it doesn't count. They are western-style work boots."

"Then ask for some pumps with kitten heels. Or better, some block heels. And don't exceed 11/2 or 2 inches. Don't buy the most expensive if you wish to go for higher heels when you have gotten used to them."

Remembering Jenny and Rosie in high stiletto heels made me decide that I would follow her advice. I thanked her again and eased my shopping into my rucksack in a way that would keep them from being wrinkled.

In the jeans store, I found a pair of jeans similar to the pair I was wearing, but in a darker blue color. I looked around in the shop and found another pair that I liked. I guess love is a better word. It was a pair of black coated jeans that had a wet-look surface. I took them in the same size that I was wearing and took both pairs to the fitting room.

shecret
shecret
64 Followers