tagLesbian SexJenny's First Time

Jenny's First Time

bypixie2002©

"Thanks for coming in, Jenny. We'll be back in touch with you."

And with those words, I figured that was all I'd ever hear about the summer job I'd just interviewed for. I'd spent half the morning getting ready to meet the manager of Dustee's, the little clothing boutique at the mall where I'd put in my application. And in about five minutes, the interview was over!

Cindy, the manager, had been friendly and she seemed really nice. She was in her late 30's or early 40's and very pretty. She had shoulder length blonde hair and brown eyes. But the thing I remembered best were her breasts. They were full and round, a perfect complement to her curvy figure.

And of course, she dressed very fashionably. I'd hoped to dress that way, too, if only I could have gotten the job at her store, where I would have received a 20 percent employee discount. I had always loved the fashions they featured, which were designed for older teens and young women around my age. It would have been a wonderful way to add to my wardrobe and maybe even earn some money to put towards a car, which I desperately needed for school in the fall.

But after such a short interview, I figured I had no chance at the job. So, I drove home in my mom's car discouraged and dejected.

I was more angry than disappointed by the time I got home. I slammed my bedroom door behind me, pulled off the cute top I'd put on especially for the interview and threw it over in the corner. My denim mini soon followed and I stood there in my bra and thong looking at myself in the mirror.

"Jesus, Jenny," I said to myself. "You're a smart girl and you're not bad looking. You smiled really nice and answered all her questions. So why would she just blow you off like that?"

Actually, I was more than not bad looking. My blondish/brown hair cascaded down below my shoulders and framed my face nicely. It was a pretty face, according to my mother, and several of the boys at school seemed to agree, as they paid more and more attention to me. Of course, that may have also been because of my 36-C breasts, which looked more than ample on my slender frame.

My favorite feature, though, was my brown eyes, which were expressive and always gave away my emotions, whether I was happy, sad, or anything else in between. Unfortunately, I had to wear glasses if I wanted to see anything, so I usually looked like a bit of a nerd. Even though I couldn't afford them now, I knew there had to be a set of contacts somewhere in my future.

As I stood there feeling sorry for myself in front of the mirror, my hands began to play lightly across my cheeks and then my lips, touching sensuously. It wasn't unusual when I was feeling down to "comfort" myself with a nice orgasm. And I thought since my Mom was away at work here in the middle of the day, why not try and make myself forget all about the failed job interview.

My hands moved lower, gliding over my chest and across the cups of my bra, feeling my nipples harden as I brushed against them. I took each nipple between my thumb and finger and pinched, bringing them to attention. The sensation traveled from my sensitive breasts straight to my pussy, as I felt myself grow moist in anticipation of touches there that would soon follow.

But just as I closed my eyes and gave myself over completely to the delicious feelings that were beginning to pulse through me, the telephone rang. I jumped at the unexpected disturbance, cursed under my breath, and ran into the den to answer it.

"Hello, Jenny?" the voice on the other end inquired.

"Yes, this is Jenny."

"Oh good, dear, I'm so glad I caught you. This is Cindy. From Dustee's."

"Oh, yes, Cindy!"

"I just wanted to let you know, dear, that I think you'll be perfect for the job. I need you to start tomorrow. Can you do that?"

Actually, I had hoped to spend the first week after school was out relaxing and hanging out with friends before starting work. But I certainly wasn't going to pass up this opportunity—especially when five minutes ago I thought I had no chance at the job.

"Sure," I responded eagerly, "I'll be there tomorrow. What time?"

"I want you here when we open at 10, so we can get started with your training. See you then."

"Yessssssss!" I shouted as I hung up the phone. Maybe this summer was not going to be so bad after all.

I spent a lot of time getting dressed the next morning. I really wanted to look good for my first day at work. I especially wanted Cindy to know that she hadn't made a mistake in hiring me. So I slipped on a cute little sun dress with a built in bra that made my breasts look full and round. The black, red and yellow floral pattern complemented my tanned skin and the thin straps showed off my shoulders nicely.

The dress hit me just above the knee, revealing just enough of my nicely-shaped legs, which were suntanned, like the rest of me—one advantage of living in the desert climate of Phoenix. I curled my hair and applied a bit of lipstick, as I usually didn't wear much makeup. My girlfriends kidded me a little about my "natural look," saying it made me look a lot younger. But I liked the way I looked without much makeup. Besides, it made it a lot quicker to get ready for school every morning.

As usual, my mother had to drive me to work. I had my license, of course, but we only had one car in the family, and she needed it to get to her office. "God, I hope I can earn enough to afford some kind of car. Being driven around by my mother at my age really sucks," I thought to myself as Mom slowed to a stop at the main entrance to the mall.

"Hi, Jenny," Cindy called cheerfully from the back of the store as the automatic chime announced my arrival when I walked through the entrance. "I'm so glad you decided to come work with us this summer."

"No, thank you! I really needed a job, and this is the one I wanted really bad," I told her honestly. "Besides, I think it will be a lot of fun working here."

"I think so, too, dear. And, if I haven't already told you, please call me Cindy."

"Oh, sure. Thanks . . . Cindy."

"All right, Jenny, let's get started."

The rest of the day went by quickly. There weren't all that many customers in the store on a weekday morning, so Cindy spent the slack time showing me around, explaining the inventory system, showing me how to operate the cash register, and all the other things that make up the wonderful world of retail. But I didn't mind at all, because the store was nice, my boss was nice, and I knew I was a lot better off that some of my friends who were spending their summer working fast food.

As the first couple of weeks went by, I began to get into a routine. I got comfortable helping customers, and it turned out that I had pretty good fashion sense. At least that's what Cindy said. She was very complimentary of how I handled customers and, especially, about how I dressed.

I'd planned to use my first paycheck to buy some clothes I needed for work, knowing the money would go a lot farther with my employee discount. Cindy even volunteered to help me pick out some things that would be good for me to wear for work. I had to wait until the store closed to do my shopping, so Cindy locked the door after the last customer left.

"Just go on into the dressing room, dear," Cindy instructed. "I'll bring you some things you'll look darling in."

"Well, uh, I had a couple of things in mind already," I protested mildly.

"It's all right," she assured me. "If you don't like what I pick out, I'll go get the things you had your eye on. Just get yourself ready to try them on."

So I headed back to the dressing room and sort of stood there waiting for Cindy. I didn't know quite what to do while she gathered up the clothes for me to try. But it wasn't long before she knocked briefly on the door, and without waiting for an answer, stuck her head inside.

"Here you are, dear," she said cheerfully as she handed me a half-dozen things she had picked out.

"Thanks," I said, taking the hangars and holding them as I looked at Cindy, who had made no attempt to close the door.

"What are you waiting for? I can't wait to see how you look in these," Cindy said.

"Well, er, I," I stumbled.

"Oh, of course, you'd like a little privacy. Just let me get out of your way." And she closed the door behind her.

Once the door was closed, I slipped out of the skirt and top that I had worn to work that day and began to try on the outfits Cindy had selected. I had to admit that she had really great taste. I couldn't possibly afford all of them, so it was going to be tough making up my mind.

As I put each one on, I opened the door, stepped out and modeled for Cindy. And her approving looks and words made me feel very attractive and special. I was so grateful to her for taking so much of her time to help me.

There was one more outfit left to try, a little black mini skirt and halter top. I hesitated a bit as I looked at them. They really were cute, if a bit more daring that most of the things I usually wore. I slipped out of the dress I'd tried on just before and stood there in my bra and little red thong wondering how I could possibly wear a bra with the halter top and make it look right.

Finally, I let the straps slide from my shoulders, unfastened the clasp, and laid my bra on the chair. As I stood there trying to get the halter top off the hanger, the door suddenly opened, and there stood Cindy, looking at me with a funny smile on her face.

"Oh!" I exclaimed when I saw her standing in the doorway watching me. Reflexively I raised the halter, hanger and all, to cover myself. My breasts were mostly hidden, but that left my bottom half totally exposed, except for the scant fabric of my little thong.

"I'm so sorry, dear, I didn't mean to intrude," Cindy said soothingly as she stood there looking at me. I could see her eyes traveling up and down my body, and I didn't quite know what to do next. Yes, I was a bit embarrassed by her attentions. But at the same time, I was flattered that she so obviously liked the way I looked.

And just as she was backing out of the dressing room and preparing to close the door, I stopped her. "It's okay. It'll just take me a second to get these on, and you can tell me if you like them."

But it didn't take just a second at all. As a matter of fact, I decided that I'd draw things out a little so I could enjoy the feel of Cindy's admiring gaze just a bit longer. I took the hanger that still held the halter top, reached over, and hung it on a hook on the far wall. As I reached upward, my full breasts swung freely and my nipples hardened a little, perhaps from the cool air conditioning that was blowing from the vent in the ceiling. Perhaps it was from something else. Whatever the reason, I could tell that Cindy noticed them, too.

After I had hung the halter back up, I was left again in nothing but my red thong, and I took my time with the skirt. I turned my back to Cindy and bent over to pick it up from the floor, where I had set it down as I prepared to try it on. I could almost feel the heat of Cindy's gaze on my tight, round bottom as I leaned forward and gave her lots of time to look me over.

Finally, I straightened back up with the skirt in hand, turned around and reached down so I could step into it. Once again, my breasts hung free and swayed back and forth as I pulled the skirt up and reached to the side to fasten it. I extended my arms to each side and smiled at Cindy and said, "Well, what do you think?"

Now it was Cindy's turn to be embarrassed. "Well, uh, oh, I think you look lovely, Jenny. But let's see it with the top." Her eyes were fixed on my breasts and her face looked a bit flushed.

So I slowly slipped the halter on, then looked back at Cindy. "You like?" I asked innocently.

"Oh, yes, Jenny! That one's a definite keeper," she gushed. "Your legs look so good in that skirt. And the top . . . ," her voice trailed off. I'm sure she didn't know exactly what to say at that point.

So, I kept the black mini and halter top, to go along with two other outfits that Cindy and I both liked. And I went home that night wondering whether my relationship with Cindy might be evolving beyond that of employee/boss.

Over the next few weeks, Cindy and I were friendly at work. We joked, kidded, and some might even say "flirted" just a little bit. Of course, I didn't think of it as flirting at the time because she was a woman. But, looking back on it, that's definitely what it was.

Neither one of us said anything about that night after work when I tried on the new clothes. We just laughed and teased a little between customers, and I could tell she liked me, beyond my simply being a good employee. Every now and then she'd invite me to join her for coffee at one of the little restaurants in the mall. It was at one of those breaks that things got a bit more personal.

"Tell me, Jenny, do you date much?"

"Oh, not really that much. My mother's a little over-protective, and I just haven't found anyone I like all that much."

"Surely a pretty girl like you must have a lot of boys chasing after them," she prodded.

"Well, I did date this guy a few times. Brian. He was pretty cool."

"Are you still dating him?"

"No, it sort of cooled down," I lied. Actually, I'd let Brian fuck me the second time we went out and he just sort of quit calling. The next thing I knew he was dating this girl a couple of years younger than me. I was really hurt for awhile, but had pretty much gotten over it.

"So was Brian like most guys your age?" Cindy pressed.

"What do you mean?"

"More interested in hooking up than having a real relationship?"

My faced flushed at this reminder of what had happened to me and I mumbled, "Yeah, I guess so."

Sensing my discomfort, Cindy reached across the table and put her hand on top of mine. "It's okay, Jenny. Just remember, it's not you. He's the one with the problem." And with that, she lifted her hand and stroked my hair, brushing it back from my face and touching my cheek lightly in the process.

"Well, I guess we'd better get back to work, dear. I hope I didn't make you uncomfortable with all my questions."

"Oh, no, it's okay." And it really was. I felt like Cindy and I had a real connection, and I was flattered that she was so interested in my boring life.

Just as we reached the entrance to the store, Cindy stopped and turned to me. "Jenny, would you like to have dinner with me Friday evening?"

I looked at her and opened my mouth to answer, but before I could speak, she plunged ahead. "I just get so tired of eating alone. I have this big house that seems so empty, especially on weekends. I'd really love for you to come over. Besides, I'm a very good cook," she smiled.

"Sure," I said, wondering a little that someone as attractive as Cindy would spend many weekends alone. "Tell me how to find your place and I'll be there."

I wasn't scheduled to work the Friday of our dinner, so I took my time that afternoon getting ready. Somehow, I felt as if I was getting ready for another job interview or something, because I had the same butterflies in my stomach that I'd felt before I went in to talk with Cindy about the job. It puzzled me a little why I felt apprehensive when Cindy and I had become friends.

I took a leisurely bath, shaved my legs and underarms, and debated whether I should shave my mound, too. Several of my friends had done it, and I thought it was sort of sexy. But my hair was so light and sparse down there that I finally decided not to bother. Besides, who was even going to see it besides me?

I picked out a bright yellow sundress and a pair of new sandals that I had only worn a couple of times. They showed off my feet, so I made sure that my toenails were done neatly with a light pink polish. I had to wear a strapless bra because of the thin straps on the dress, and I slipped on a matching thong.

Unfortunately, I was in a bad mood by the time I arrived at Cindy's because Mom had to drive me. She needed the car, and there I was again, being driven around like I was in junior high. She let me out in front of a really nice house that, according to the address, belonged to Cindy.

Mom waved and drove away when the front door opened, and Cindy gave me a little hug as I stepped into the foyer. She looked very pretty, dressed casually in a pair of nice ivory colored shorts and matching top with spaghetti straps. I could tell she wasn't wearing a bra because the top was kind of clingy and hugged her full breasts, which jiggled noticeably as she led me into the living room. I even thought I saw just a hint of the dark circles of her areolas under the thin fabric.

Her soft blonde hair brushed against her nearly bare shoulders, and I could see that her nails were freshly done, adorned by bright red polish, which matched her lipstick exactly. There was something about her hands, those fingernails, that made my butterflies flutter just a little more.

"Wow," I said as I looked around the spacious living room with its high ceiling and large windows that looked out at a pool in the back yard. I suddenly realized that I sounded like a kid who had never been anywhere, but I just couldn't help myself. It was one of the nicest houses I'd ever been inside. "This is great house!"

"Thanks. I got it when my ex and I divorced," she explained. "It's about the only thing I ever got from him." She smiled as she said it, but I knew from the tone in her voice that she wasn't kidding.

Cindy poured us each a glass of wine and motioned me over to the sofa, where we sat and chatted for awhile. I'm not sure exactly how long, but it was long enough for me to have a second glass.

Then we made our way into the dining room, where Cindy had set the table beautifully for just the two of us. She took a match and lit two candles in the middle of the table, and the low light and the wine made me feel very relaxed and mellow.

Dinner consisted of a wonderful pasta dish that Cindy had made herself, along with a green salad and hot bread. And, of course, more wine.

All through dinner, there was a lot of talk about work, how sales were going, and a little gossip about which employees happened to be dating each other that week. Everything flowed very easy, very natural.

When we finished the meal, Cindy motioned toward the living room and I went in and sat on the couch. In just a moment, she joined me and we were sitting side by side on the long sofa, which was covered in soft chenille. There was a little more small talk about work, then Cindy surprised me.

"Tell me, Jenny. When Brian kissed you, did you enjoy it?"

I couldn't even believe she remembered that conversation. "Well," I responded hesitantly, "I suppose so. It was sort of exciting . . . different."

"Did he try and touch your breasts?"

My face reddened. I was getting uncomfortable the way the conversation was going, but something about telling these things to Cindy was sort of sexy, too.

"Yes, after we kissed for awhile, he started caressing my breasts through my top. You know, sort of holding them, squeezing."

"And how did that make you feel?"

"Well, I was kind of uncomfortable. But at the same time, it excited me. I knew I should tell him to stop, but I didn't really want him to stop."

I could feel my nipples getting hard, just like they did when Brian was playing with my tits. But I wasn't sure whether I was aroused at the memory of that experience or turned on by the fact that I was describing it to Cindy, who seemed to be hanging on every word.

As we talked, Cindy moved a little closer and began to run her fingers lightly through my hair and look deeply into my eyes. She had this funny expression on her face, sort of like the one I had seen that night in the dressing room.

"How far did you let him go, dear? Did he touch you down there?"

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bypixie2002© 17 comments/ 131259 views/ 28 favorites

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