Teaching Penny How

These stories are based on a series of emails and text messages shared with a very special friend and fan. Thank you Penny for your encouragement and for sharing your fantasies and dreams with me. I hope these stories prove to be worthy...

We first met at a museum fund raiser. Everything was tres elegant and I was feeling slightly out of place once I'd given my donation, but the buffet table beckoned and the bar was free and open, so I stayed. I had a drink in one hand and a full plate in the other and was backing away from the buffet when I literally ran into her. I turned, apologizing even before I saw her.

"I'm dreadfully sorry. I didn't mean to mash you!"

And I stopped open mouthed. I was eye to nipple with the most glorious set of breasts I'd seen in a good many years and the owner was laughing merrily. I continued to look up. She had to be at least a good 6 inches taller than me, not counting the addition caused by her three inch heels. Tall, and brunette she gave new meaning to the term BBW. She was a goddess in every way.

"Mash ME?" She was still laughing. "Nothing personal but I doubt your ability to actually MASH me."

Her laugh was infectious and I had to admit, despite my own status as a BBW, that standing next to her and comparing our relative height differences made the idea of ME mashing HER ludicrous. We were both laughing as we introduced ourselves and she invited me back to her table. We got on, in her words, 'like a house a fire', talking and laughing non-stop for several hours. Her husband passed by, talking with another couple, at one point and she interrupted them long enough to introduce me around. I had noticed her rings but even after the introduction I wasn't a hundred per cent certain of her sexual orientation. We'd made more than one trip back to the bar and under the impetus of too much wine our conversation had gotten increasingly flirtatious -- on both our parts. She seemed as avid as I was to reach out and touch and it seemed to me that a lot of sexual innuendo was being passed between us.

Before the fete was over we had made plans to meet for coffee in the morning and when her husband came to the table, jingling his car keys, she kissed me goodnight. Not a quick peck on the cheek mind you but a full on the lips, slightly open mouth, very breathy and not overly brief, kiss. I enjoyed it immensely. Bi or straight, the girl knew how to put her heart and soul into a kiss. I did sneak a quick peek at her husband and he was examining his cuticles and smiling to himself. His reaction didn't tell me anything more than I already knew, which was nothing really and I went home, horny and frustrated. Masturbating until I came twice before I could relax enough to sleep and then I dreamed about making love to the Mother Goddess.

As eager and early as I was arriving to the coffee shop the next morning, Penny was already there and waiting with that radiant smile of hers. She greeted me with a hug and a kiss just two degrees cooler and more sober than last night's goodnight. She was even prettier in the daylight in a short and breezy sundress that displayed her cleavage to advantage. I hoped I wasn't drooling overtly but she did have the most beautiful, full, round figure. I wanted to bury myself between her breasts, suckle at her nipples and feast between her thighs. We talked quietly but with gentle touches, leaning into each other's space and with occasional blushes on her part. Finally I couldn't stand the suspense any longer. I had to know what she wanted.

"So tell me Penny, honestly please. I know that you're married so you're probably not lesbian. Are you bi?"

She ducked her head slightly and blushed, sipping her coffee to stall for time.

"No...not really...at least...."

I put my hand over hers, "At least not yet, but you're curious aren't you sweetheart?"

Her eyes filled with gratitude at being understood as she answered, "Oh God yes! I want to...try...but I don't know what to do, how to start."

I scooted closer to her in the booth, my hand slipping under the loose skirt of her sundress and creeping between her thighs. She sat up straighter for a moment but her nipples tightened with excitement, and I realized she'd come braless today. I smiled in reassurance and moved my hand a little further up -- far enough to feel her heat and moisture. Moving her sodden panty aside I gently stroked her velvet folds. She trembled a little but she was plucky -- she leaned back and spread her thighs more, giving a pleased half moaning sigh.

"So tell me, Penny, what are your plans for tomorrow? Doing anything?"

Her eyes flew open, glancing around quickly to see if anyone was watching. No one could overtly see me playing with her, but anyone walking by and paying close attention would have known what was going on. I smiled to myself enjoying the thought of showing her off.

"Umm, tomorrow? No plans. Nothing really important anyway -- I usually have lunch and go shopping with my sister on Thursdays but I can do that any time."

"Good! How would you like to be my plus one at a pool party tomorrow? Plan for plenty of food, wine and other happy making substances and I'll pick you up early. Don't plan to get home until very late if at all. Tell your hubby if we get too drunk we won't risk driving we'll just all grab pillows and blankets and sleep over like a grown up slumber party."

"Your plus one? Won't that seem a little odd Ali? I mean normally..."

I interrupted her laughing, "The term normal does NOT apply to this pool party, Goddess, you'll see."

I slid my finger deep into her wet depths before removing my hand and pointedly licking my fingers, winking at her as she tried to pull herself together. I ambushed her again while saying goodbye, pushing her up against the side of her car. This time I pulled her skirt to her waist but embraced her so closely that not much could be seen. Still, her head rolled back on her shoulders and she sighed happily when I began to finger fuck her, nibbling on her neck and cleavage. She was surprisingly docile. The first time I'd seen her I'd expected an Amazon, but she wanted...no she needed me to lead her and guide her. And I was more than happy to indulge her. Before saying goodbye for the afternoon I instructed her to dress sexy, if not outright slutty for the pool party, because I wanted to show her off and I wanted everyone there to want her.

She was as radiant as the sunrise the next morning in a neon orange cutaway that revealed more than it covered, and a gauzy pink...something....it looked like it may have started out life as a negligee. Her nails were the perfect coral to complement both colors. High wedge sandals had her topping six feet plus and meant that she would draw attention, willingly or not, wherever she was. I really wanted to stop for coffee and send her in but I'd already stopped and coffee and bagels were nestled in the center console. Damn my OCD, I thought.

I kissed her thoroughly, taking care not to muss her but sliding my eager hands over her taut nipples. She was hugely excited, despite her anxiety about what might or might not occur and she trembled but responded eagerly with her own explorations. She was rewarded fairly quickly since I was wearing a long boldly floral halter dress and only string bikini bottoms. Her inquisitive fingers touched my nipples and I groaned happily, nibbling on her bottom lip. I leaned closer to her, kissing along her jaw to her ear lobe. I nibbled and sucked it enough to raise some gooseflesh before I pulled away regretfully.

"If we don't leave now, we're going to be very late arriving, and as tempting as you are here, I can't wait to see you with the sun reflecting off your...bits..."

I winked and started the engine.

"Fortunately though, this is an automatic, so I have a hand free. At least until the road starts to get tricky."

I did actually concentrate on the driving but managed to tease and tickle and stroke her enough that her nipples stayed taut and her pussy grew increasingly damp. At the party I introduced her around, got us situated with lounges -- positioned in the sun now but they would be in shade later in the day as it grew hotter. I made sure she knew where cold drinks, hot and cold food and all the necessary facilities were. Once everyone had arrived and been introduced it didn't take long for someone to suggest we all go bare, 'since it's just us girls'. The idea was roundly applauded and immediately acted on. Penny seemed a little body shy, even though she was not the only BBW there -- counting myself too of course. I offered to help her apply sunscreen to her back and she accepted.

I took a generous amount of sunscreen in my hands and rubbed them together to warm the lotion before beginning with long slow strokes, over her shoulders and down her back. My hands circling back to repeat the motion again and again as I felt her begin to relax -- her muscles losing some of their tension. Applying more lotion to my hands I began slow circular stroking of her shoulders, continuing that motion down her back -- around her sides and over the side swell of her breasts -- further down, circling around her hips and the cleft of her ass. I thought I heard a quiet moan. If she was watching, other members of the group were pairing up...or whatever multiples they desired....and starting to kiss and stroke and fondle. Leaning forward I murmured into her ear.

"Is there any place else you need help with the lotion, Penny?"

I gently nibbled her ear lobe and kissed her neck where it met her shoulder. She turned to me, holding the lotion. She blushed a little but smiled and her eyes were clear and steady as they met mine.

"Yes, please...I'd hate to burn any of the important bits."

She looked down at her impressive DD breasts and smiled wider. I nodded in agreement, squirting lotion into my hands and rubbing them together. Looking down myself I could feel myself growing wet and swollen at the first full sight of her naked breasts. Full, round and high with just a slight teardrop shape, the areola were large, dark and hard as mulberries. I licked my lips in anticipation and as I did a shiver of gooseflesh ran over her, making her nipples even harder. Her mouth was open as she began to breathe more heavily and I leaned forward to kiss her deeply. My tongue danced with hers and I took some small nipping kisses along her jaw and down her neck to her shoulder. Around us there were the initial sighs and moans of pleasure and love making and I could feel my body's increasing response to the stimulus. Sliding closer to Penny, I straddled her thigh, rocking my hips a time or two to spread my heat and juices against her skin. I pushed my knee forward until it pressed firmly against the moisture of her own arousal and felt her respond by pressing forward against me. I realized we had a small group of 'fans' watching us in between their own kisses and touches.

Using the tips of my fingers and light feathery touches I made spiraling circles over and around her breasts. Her nipples had been hard to start but they grew increasingly rigid and deeply pebbled and were a beautiful, dusky rose color. My fingers continued to make their light circles over and around her breasts and nipples, along the soft sides of her ribs and the tender skin below her tits, over the swell of her belly and down to her hips and back to her tits again...never stopping. As I stroked her skin I realized I was murmuring to her, telling her how beautiful she was, how exciting and sensual and how much I wanted her, how much I was enjoying making love to her and some of the things I wanted to do to her...and with her.

Finally, I couldn't resist her any longer and bending close I ran my tongue around and over one of her luscious looking nipples. I heard her little gasp and moan of pleasure and as I did I heard a click and snap and realized that one of the women watching us had cuffed Penny's hands behind her back. I smiled and nodded my approval and bent back to Penny's breasts, switching my attention between her nipples as I licked and sucked, occasionally nibbling or gently slapping. My intent was never to hurt her but I knew from personal experience how stimulating a spanking, or light slap or slight nip could be. Motioning to the women around us, I indicated what I wanted and they loosened her cuffs momentarily, laying her back gently with her arms stretched overhead. One of the pool side tables was anchored nearby and they were able to lock her restraints around that anchor, holding her in place.

I looked down at her possessively, pressing the full globes of her tits together in a futile attempt to suckle both her nipples at once. But she had other treasures I wanted to explore and pleasures I wanted to share with her. Suckling one nipple deep and hard I let my other hand roam freely over the sweet gentle swell of her belly and down the slippery slope of her vulva. She was swollen, open and dripping wet and as my fingers moved over her, she moved her legs as far apart as possible. I almost came, just knowing that she wanted this as much as I did. I slid one, then two fingers deep inside her, pressing up firmly against her G-spot while my thumb circled and feathered across her clit. The little pearl was already hard and throbbing against the skin of my thumb and I knew her first orgasm wasn't going to be long in cumming.

I didn't want her to wait too long. I wanted it to be hard, fast and explosive for her. I grazed her nipple with my teeth, nibbling at it lightly and flicking it with my tongue -- much as I would do to her clit later. Watching, her eyes were closed, she was biting her bottom lip, her back was arched and her hips were beginning to rock up to meet my hand.

"Spread your legs wider sweetheart, show everyone what a beautiful wet pussy you have and how much you like fucking," I urged in a low hoarse voice. "And cum for me. Cum for me now, baby!"

We are surrounded by the smells and sounds of sex -- wet, slapping hands in cunts -- the smells of dripping arousal -- happy moans and groans of pleasure and sucking, licking noises. My eyes gaze down and over the swell of her belly where my fingers lie buried in the thick mat of her dark bush. She gasps out an 'oh' of sudden intense pleasure when I slide a third finger inside her, curling them so I can press my knuckles firmly into her G-spot. My thumb continues to tease and caress her clit. Feathering touches around and over and to and fro, increasing the speed and pressure as I increased the speed and pressure of my fingers in her cunt, and my lips and tongue against her taut nipples.

"Oh god....oh no....I'm....my god...."

She's bucking and thrashing against me as the orgasm washes over her. I can feel the spasms of her cunt gripping and milking my fingers but I don't stop. Suddenly Penny's eyes fly open and then seem to roll back as a wave of red heat flushes throughout the skin of her body. She cums again, this time so powerfully it almost hurts my hand with the force of the muscle spasms. It leaves her limp and panting, flushed and rosy skinned. My hand is drenched with her nectar and I pull it out of her pussy, making a point to show how the juices drip from my fingertips before licking a finger clean.

"Now THAT's what great cum tastes like. Sweet as honey and just a touch of salt! You taste as good as you look Goddess."

I tell everyone as I smear the remaining juices around one of my own hard nipples. Crawling over her I press my hard, wet teat against her eager lips and she sucks it in, slow and deep, as her tongue circles the taut point. I give a deep, happy moan of pleasure as I think about where and what I want her lips and tongue to do next. Somewhat regretfully I pull my breast from her mouth with a slight pop, bending to kiss her in a small indulgence. Straddling her face I spread my shaved pussy lips wide above her.

"Now sweetheart, it's your turn." I coo as I nestle my cunt against her lips. "Make me cum, Penny baby. Eat my pussy and make me cum!"

Her tongue takes a somewhat hesitant swipe across my pussy, landing purposely or more likely by chance on the throbbing pearl of my clit.

"Oh yes!"

I groan happily, indicating to one of our onlookers that they should unlock her restraints. Her hands grip my hips, pulling me down even closer to her mouth and I surrender to her attentions, using my fingers to pinch and twist my own nipples and doing my best to mimic the feel of her lips and tongue. I know I'm not going to last long, my thighs are already trembling and I rock involuntarily against her mouth, doing my best to keep from either drowning or suffocating the woman. She seems to sense how close I am and focuses all her attention on the throbbing peak of my clitoris, licking and sucking eagerly.

"Yes...YES....That's it!!! Don't STOP!!!!"

I'm screaming out as my juices flood her face and she struggles to drink them all. I slide down, cuddling next to her, kissing and tenderly licking my juices from her face in between murmuring sweet endearments.

"You are such a treasure, Penny, beautiful, brave and adventurous. I am absolutely lost in lust for you and have such hopes for a long series of continuing adventures and experiences together."

Sliding a hand over her sweet body I enjoy the swell and curve of her breast, tweaking her nipple in passing. Sliding over the swell of her belly I reach the thick thatch of her pubic bush. She's so wet.

"My beautiful girl, you seem to be as excited as I am -- enjoying this as much as I do. "

I eel my way down her body, working my way between her thighs, using my hands to part the black fur covering her treasure.

"You're so beautiful Goddess. Like some rare tropical flower after a rain -- wet and shining with your dew, swollen and rosy with excitement."

I lick carefully around each side of her channel, loving the taste of her arousal. Burying my face against her I insert my tongue as deep as I can while I feel her trying to grind against me. Her clit stands swollen and proud, demanding my attention and I gladly wrap my lips around it, flicking it lightly as my fingers try to fill her cunt, fucking her firmly. Then using my wet hand to stroke, I lightly tug and tap her plump labia, drawing blood to the surface of her skin and increasing her sensitivity.

Keeping my primary attention on her clit, I wrap my lips and teeth gently but firmly around her little woman cock, suckling it and flicking it. I can see that the women who have been avidly observing our antics have taken this opportunity to each obtain one of her breasts, sucking it greedily. Her back is arched, head thrown back and her bottom lip is buried between her teeth as she gets closer. Her own hands are busy exploring the feminine forms and folds available to her and I hum happily with lust and approval. The vibration of my humming is transmitted from her clit to her brain and back again, seeming to ramp up her pleasure.

Sliding my fingers down the dampness of her folds and crack, I reach her anus eliciting a tiny squeak. I can't tell if it's a noise of protest or simply surprise but I don't remove my finger, continuing to circle the tight little spiral with the pad of my forefinger as I would with my tongue if it weren't otherwise occupied. I feel her clitoris beginning to pulse with her heartbeat and I know she's going to hit her orgasm soon. Her hips begin to buck and rock, her cunt spasms, juices flow and she is squealing and making lovely happy noises. In the middle of her orgasm I slide my forefinger deep inside her ass, changing the tone of her squealing briefly. But as I fuck her sweet, tight asshole and suck hard at her clit, our helpful friends are sucking equally hard at her nipples and she peaks again, and then again before collapsing limply in a near faint.