Picture This, Chapter 2

  • Posted on July 13, 2015 at 9:31 am

By Jeneee

Being a waitress sure has its moments. Couples eating out together sometimes fascinate me, no matter their age. And I don’t believe I mentioned my age yet so just so as you know, I’m twenty-two, a high school graduate and hoping to save enough money to eventually go to college to study photography – maybe even open my own studio once I get some experience. A lofty goal, I know but it has been a dream of mine for several years. I’ve always loved taking pictures, especially portraits, and I enjoy looking at the works of other photographers, marvelling at the poses and expressions they seem to be able to coax from their subjects.

But my life changed drastically when, a few months after I’d finished high school, my mom came home from a visit to her doctor and informed me that she had cancer – and that it was terminal. She had maybe a year to live. I was in shock. Deep shock. We hugged each other and cried together for a long time until we both eventually ran out of tears. My college plans were put on hold indefinitely.

Mom and I had always been close, especially after dad left us when I was in my early teens. She’d helped me to deal with the realization that I was a lesbian, and had supported me all the way. Mom even confided to me that she was bisexual, and although she didn’t really come out altogether, it was one of the contributing factors to dad leaving us. That and learning that his daughter was a lesbian, for which he also blamed my mom for not bringing me up right. We could never figure out what he meant by that. Men! He at least had the decency to come to mom’s funeral, and I still see him occasionally, but he’s never accepted me for what I am, and never wanted to meet any of my girlfriends – even though I’ve only had two or three since I was in my teens.

Anyway, my mom was able to hang on for two more years with me putting my life on hold to look after her at home. Even though I knew what was going to happen I was still devastated when she eventually passed away. It took me quite a while to get my life back in order and I was lucky our house was paid off and we had a bit of money saved, so with that and the life insurance I inherited I was able to get by for a little while.

But I knew it wouldn’t last for long. I had to get some money coming in especially if I eventually planned to go to college. That’s when a girlfriend suggested I take a job as a waitress where she worked. Tips were not bad, she told me, and who knows, she laughed, you might even meet a guy. So now you know she was a girlfriend, but not a ‘girlfriend.’ She had no idea I was a lesbian. I eventually took the job and even though it was tiring it wasn’t all that bad. She was right, tips were good most days, and I was able to make enough money to live on and was also able to put a little away for my college tuition.

As I said a while ago, couples eating out sometimes fascinate me. I’m not all that bad looking – even though I don’t match up to Kayla – and I do get my fair share of looks from diners at the restaurant. From men especially. Our waitress outfits are attractive and close fitting and I enjoy the tightly strained smiles wives or girlfriends send my way when they notice their men giving me the eye – I’ve been told my butt looks great in tight pants. Little do they know that it’s them I’m eyeing back though, and not their boyfriends – at least if I find them attractive, that is. Some of them are so insecure that they often go out of their way to try to regain the attention of their partner, showing a little more cleavage or leg, all of which plays right into my hands. If they only knew I was a lesbian, I’d chuckle to myself.

From my recent encounter with Kayla and Amanda you’ve probably guessed that I also don’t discriminate as far as age is concerned – young girls have appealed to me since I was a teen. I had several babysitting opportunities when I was in high school and frequently found myself with a sweet seven or eight year old princess snuggled in my arms slowly falling asleep on my lap as we watched television together before her bedtime, often after having helped her with her bath. Tickling games were always popular with the younger ones and I often feigned being super ticklish in order for them to explore and discover my most sensitive spots – which of course included my boobs.

Young girls are so curious about the bodies of older girls and when they discovered, usually by accident at first, that my boobs were very ticklish – which of course they really aren’t – they’d do all they could to have me in fits so that they could continue to explore what they would eventually develop themselves. I wasn’t exactly voluptuous as a teen – nor am I now – and since my boobs were rather small I’d usually not bother wearing a bra. I do, however, have prominent nipples which rapidly hardened during these playful sessions and were another source of fascination for some of my younger sweethearts. I remember the time one particular little nine year old girl who had continually groped my breasts – yes, her tickling had progressed to groping once my giggles had died down a bit – shyly asked if she could see them.

“Only if you let me see yours too, sweetie,” was my quick-thinking response. She was a little too old for me to have ever had the need to bathe her so I hadn’t yet had the pleasure of seeing her naked young body which, although small for her age, was quite nubile. Now was my chance.

“But I don’t have any boobies,” she replied. “See?” And she quickly lifted up her loose pyjama top for me to see her almost flat, pale chest. I peered closely at her and ran the tip of my index finger over one of her tiny pink nipples. Together we watched it harden into a cute little point.

“I think it wants to start growing now,” I teased, “don’t you? Want me to help it even more?” I asked, with a sly smile on my face. She giggled and nodded. Bending down I first kissed the tiny tip of her sweet little bud and then swirled my tongue around it as she giggled even louder. Then I sucked harder on it, drawing it out from her chest, softly pinching it with my fingers. Her giggles died down and I heard the start of a moan deep in her throat – the little fox was enjoying it. “Does that feel good, honey?” I asked as I drew away and looked into her deep blue eyes.

“Mmmm,” she murmured, her face a little flushed. “But you said I could see yours too,” she quickly remembered, reaching out to touch one of my boobs through my tee. “Can I?”

“You sure can, honey,” I told her, lifting my shirt up over my firm boobs, nipples now hard and winking at her. She shyly reached up and ran a hand over one, tentatively squeezing it in her tiny palm, then reaching up with her other hand to delicately pinch the nipple of my other breast, drawing it out even further. I lifted her up onto my lap so that she could comfortably continue her exploration while my right hand slipped beneath her pyjama top again to caress her almost flat little chest.

She looked at me with a cute smile on her pretty face. “Do you think mine will grow to look like yours soon?” she asked, “If you keep playing with them like that?” she added hopefully.

I nodded. “I’m sure they will, hon. And they may even grow bigger than mine,” I added.

“Will yours grow bigger yet, too?” she wanted to know.

“Maybe,” I responded. “But my mom’s were small like mine, so I’m not really sure.”

“My mommy’s are big and they bounce all around when I play with them,” she giggled.

“Your mom lets you play with her boobies?” I asked, somewhat surprised.

“Yes, and it’s so much fun to see them jiggle,” she said. “And she even let’s me suck on them, too,” she told me proudly.

She cupped one of mine in her tiny hand and tried to jiggle it around but without success. “Mine are too small to bounce, sweetie,” I explained somewhat ruefully.

“What if I kiss them like you did mine? Would that help make them grow bigger?” she asked shyly. Now I ask you, can you see me refusing an offer like that?

“It might,” I winked at her with a smile. And needing no further encouragement she immediately stuck out her tongue and started to lick the dark brown, wrinkled nipple of my left breast. Then, copying what I’d done to her, she closed her mouth around it and sucked it like a baby. I shut my eyes, moaning softly, telling her how good it felt. Spurred on by my encouragement she sucked even harder and my hand then automatically increased the range of the caresses I was administering to her chest, circling down lower over her soft tummy, squeezing it gently as her mouth and tongue aroused me even further. My hand continued its downward journey and eventually met the waistband of her panties under her pyjama top. Debating whether to slide under the silky material or not I elected to move my hand down over her panties until I was cupping her prominent mound beneath, squeezing it softly, causing her to almost bite my nipple as this new sensation overtook her.

She pulled back from my breast and looked at me, a glazed expression on her face as I ran a finger gently between her lubricating lips through her panties. “What are you doing?” she whispered. “That makes me feel so kinda funny. Like I gotta pee or something.” I kissed her softly on her pretty mouth.

“No, sweetie, you don’t have to pee,” I explained. “That’s just the feeling that big girls get when they play with each other like that.”

“But I’m not a big girl yet,” she stammered, still unsure of what she was beginning to feel.

“Do you want me to stop then?” I asked her.

“N-no. It makes me feel so good, but like funny.” And with that she pushed back harder against my hand as if to assure me that it was okay for me to continue. Not needing any more encouragement than that I once again began to caress her hot little pussy through her silky panties and leaned down to kiss her again, this time not pulling away from her sweet lips, but opening them slightly so that my tongue could begin to explore her mouth even more. She kissed me back even harder and my hand felt her panties becoming damp from my caresses as she started to squirm a little in my lap. Pulling the crotch of her panties aside I now felt the soft wetness of her delicate lips on my fingers for the first time as I slid one gently between them. She was so wet and slippery and I could feel her little button becoming hard. Our kisses became even more intense now as I fingered her sweet pussy, soon managing to slip the tip of my index finger inside her tight vagina up to the first knuckle, feeling the soft silkiness of her now soaking little treasure. At that moment she squealed and stopped kissing me, snuggling her head firmly against my shoulder, her mouth against my neck, urging her pussy harder against my probing hand.

“Ohhh, Gloria!” she cried. “Please, don’t stop, that feels…oh…so good…I…ohh…” She didn’t have to worry – I wasn’t about to stop. Her hot breath came in short, quick bursts against the side of my neck as she alternately whimpered and squealed, squirming urgently against my probing finger, her arms wrapped tightly around me. When her orgasm finally hit her she froze, and except for the slight, uncontrolled spasming of her hips it was as if I were holding onto a statue – a very hot and sweaty statue. I held her lovingly until she started to breathe again. Slowly she released her stranglehold from around my neck and drew back looking in wondrous confusion into my eyes.

“W-what happened to me?” she half whispered. “I never felt anything like that before.”

I brushed back the hair from her eyes and smiled. “You had your first orgasm, sweetie,” I told her.

“My first what?” she asked, her eyes widening in amazement.

“Orgasm,” I repeated. “That’s what big girls have when they play with themselves, or when someone else plays with them like I did with you. Did you like it?”

“It felt like I was going to explode or something,” she told me. “But I didn’t want it to stop. No, I mean, I couldn’t stop. It felt like waves going through me…like…” she trailed off.

I giggled. “That’s a pretty good way to describe it, sweetie,” I said. “It’s hard to put into words how good it feels.”

“Does that mean I’m a big girl now too, then?” she asked. She smiled big when I nodded yes.

And I remember how she looked when I finally put her into bed that evening – such a contented, glowing expression on her sweet face. As I bent down to kiss her goodnight she asked if we could do it again next time I babysat her. I told her yes, and much more too. She was asleep almost immediately. And yes, we did much more the next time. But that’s another story.

Now, five years later, here I was dreaming about what might happen next Sunday, when Amanda and Kayla came to visit. Somehow I sensed it might turn out to be a little more than just a thong fitting session. I sure hoped so.

Continue on to Chapter 3


1 Comment on Picture This, Chapter 2

  1. David says:

    Mmmm another great chapter Jeneee, well written and detailed. I love the back story about her teen years and her babysitting experiences. Looking forward to continuing.

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