Teaching Penny How Pt 02

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...

(It is recommended that you read Part 1 first for necessary background information and references.)

I wake before you to the sensation of someone eating my pussy. Without even opening my eyes I reach to cradle the head between my thighs. I slowly begin to realize it's not your lips on my snatch when I wake enough to realize you're still sleeping soundly next to me. I manage to pry my eyes open and realize my ravisher is our hostess Lynn.

I'm teetering on the rim of another orgasm when Lynn reveals her true purpose. She's wearing her favorite 'toy' - a dual strap on with a large black cock for fucking others, but concealed within are fitted plugs to fill her cunt and ass and a knob that rubs her clit every time she thrusts inside someone. She let me wear it at a party once. I fully understand why it's her favorite!

I am wet and ready and the big cock easily slides into me, filling me completely. Lynn kisses me passionately, grinding the phallus deep inside. Our breasts and nipples rub together - a much different sensation than rubbing against hard muscle and chest hair though both are pleasurable. Lynn strokes with the strap on, varying tempo, angle and depth to delight both of us, and I realize you're awake now and watching when you reach to pinch and tweak my nipples.

Having you there, awake, and actively sharing as we fuck sends me over the edge while Lynn stiffens above me with her own climax. Pulling away from me she slips between your thighs. Others are waking and joining us too. There are breasts and pussies everywhere. I see asses stuffed with plugs, nipples bearing clamps, hands holding vibes and dildos.

You are gasping and moaning as you cum again and again. Pussies fill your hands and mouth while lips assault your breasts and someone I don't recognize is sucking your toes. A young college girl is riding my face, her own lips sealed around my clit while she manages to fuck my cunt and ass simultaneously with a two headed vibrating toy.

It is some hours later and we are both pleasantly tender and fatigued when we leave for home. I pull into a rest area along the way, turning to take you in my arms.

"Thank you for agreeing to go with me today, Penny. You were wonderful and I loved every minute of the day, having you there to love and to share. Tell me Goddess, honestly, did you enjoy it? Was it what you wanted? Expected?"

We talk for some time about your feelings. How you enjoyed the experiences and sensations. How being shared with others was unexpected and gave you mixed feelings. While it was sexy and thrilling you didn't want me to feel bad if I had wanted to keep you to myself. I explained that my exhibitionist streak is fulfilled when we love each other publicly so that others can see us, while my voyeurism streak loves watching while you are being fucked and cumming publicly - regardless of who or how many partners you have.

As we talk I get an idea for our possible next adventure. I ask if you would accompany me to spend a day at the nude beach. Somewhat hesitantly you agree. It seems to be something you always wanted to do but haven't had the courage - feeling self conscious about your body image. Regardless of your doubts you agree to go and plans are made. We spend much of the remaining drive, and next few days, talking about our plans.

When the day arrives I can tell how nervous you are, even before we get to the beach. Once there I find us what I think will be a good spot - above the high tide line but not too far from the water otherwise, the spot is somewhat secluded by dunes and rocks to the sides and back, but opens wide in the front for viewing. It isn't deeply sheltered but will give you an illusion of privacy and seclusion that is, in fact, just an illusion.

I spend some time cuddling you and murmuring encouragement and endearments. I coax you into stripping down and revealing your lushly perfect body. You are truly gorgeous Penny my love and my pussy swells, starting to drip just looking at you. Unable to resist I push you back against the spread blankets, bending over you to nibble and lick all your lovely body. You make a half-hearted gesture to push me away, protesting that people might see.

"I certainly hope so, my love. That's one of the main reasons we're here!"

I reply before tweaking your nipples to hard, pebbled peaks. I lick and suck each one briefly, then spread your sweet thighs and make sure that you are also aroused and showing it. Your pubic bush is matted and your thighs gleam with moisture.

My own labia are visibly swollen - my thighs equally shiny and my bald cunt allows my swollen clit to peek from between the folds. We are ready. Pulling you to your feet we go for an early stroll down the beach. The wet sand near the water's edge makes for easy walking. It is early and there aren't many people here yet. I intentionally haven't picked a family oriented portion of the beach. What families may arrive will likely do so later in the day and with older children. The surf here can be rough at times which explains the morning abundance of boards and wet suited bodies.

As we walk down the beach I pause periodically to enjoy you, keeping you rosy skinned, hard titted and wet...so very wet and tasty. I make a point once to finger you - then slide my slick fingers into my own wet cunt. Pulling up a hand now covered with our mingled juices I use one finger to paint your nipples and areola. I lick one finger making 'mmmmm tasty' noises before pressing the last damp finger to your lips.

Your mouth opens obediently, engulfing the juice dewed finger. You suck at it while your tongue slicks it free of our nectar. Oh Goddess, I can hardly wait to feel your mouth against my sex again where it belongs. I suck your nipples for a moment, making them even more hot and rigid and then blow gently across each one. You moan quietly with pleasure as gooseflesh rises on your skin.

As we turn to continue walking you realize with a start that we've once again drawn a small audience of watchers - this time of both sexes - and you blush rosily from your cheeks to your toes. It is particularly pretty watching your blushes covering your magnificent breasts and the full moon globes of your bum. I stroke down your back and over your ass lovingly and somewhat possessively, finally sliding my fingers between your cheeks to gently finger the tight rosebud of your asshole. Someone behind us applauds and you blush even more, turning nearly scarlet in the early morning light.

Ahead of us on our return to our spot are two young surfers, male I think, taking a brief break before heading back out to sea. I walk you over in front of them and introduce you.

"Good morning guys. This is Penny and Penny likes to show people her beautiful cunt." (You blush but stand up straighter, stoically looking straight ahead.) "Would you like to see Penny's beautiful wet cunt?"

Quick affirmations from both the boys make me slide to one side behind you, directing you to 'spread your legs and play with your nipples for them' I kneel behind you. Reaching around your hips I press my face up into the cleft of your ass. I feel you tremble slightly and try to spread your legs even further.

Thinking how beautiful you are, how sweet, sexy and tasty I move my hands between your legs and forward so I can lift and separate your folds, showing these boys your rosy wet core. Pressing even closer with my face my tongue locates and rims your anus. You groan and tighten briefly when you realize the young men in front of you, now rubbing visible erections, know exactly what I am doing.

I take one hand and smack your bum sharply, leaving a clear imprint of my hand, while I mutter 'stop that'. The hand print starts off white turning red against your skin leaving a clear indication of both possession and vulnerability that is powerfully erotic. You make an effort to settle and relax.

The young men come forward, asking to touch you and I tell them that each can use one hand only to hold your folds apart. That they can kneel if desired for a closer look but that only I can finger you, fuck you or tongue you. I tell them to take their time on their own pleasure so that they cum when you do. And then they can spray their cum all over your sex. Not inside your pussy and not pressing their cocks against you but ejaculating all over you.

Having set the stage to my satisfaction I bury my face against your asshole again, tickling and tonguing the tight sphincter. Warm hands of strangers reach to touch your most private areas and I feel you tremble slightly - I can't tell if you're reacting more from fear or arousal, but when I reach a hand to stroke you, I find you are still warm and wet, your clit is still swollen and hard.

I wish I had extra hands so that I could touch myself too but will have to content myself by rubbing my sex against my leg and heel. Continuing my attention to your anus I use my fingers to fuck you, rubbing your clit with the other hand. The boys are watching so closely now that I can feel their warm breath on my fingers and know that you can feel it against the sensitive skin of your vulva as well. You are trembling and panting constantly now, muttering a constant litany of 'oh god' and 'oh fuck' before shifting to 'oh, oh, OH'. I continue to fuck you, stroking firmly against your G-spot. I can hear the wet, slapping sound of the boys masturbating as it speeds up. I use my fingers to begin lightly and rapidly flicking over your clit while my tongue continues to assault your ass.

"OOOOHHHH FUCK I'M CUMMING!!!" you wail.

The boys press their cock heads close as they spurt their jism over your pussy and thighs. We three help to support you, holding you upright until you can stand on your own again.

As you and I continue down the beach and get closer to where we left our things, I see what I've been expecting. There's been a significant addition of 'gear' to what we brought and three fine looking nude men are standing there. Two are younger, well muscled in every aspect and one is my age. His rugged face splits in a wide grin as he sees us approaching and he waves and gives a piercing wolf whistle. You are puzzled. You no longer recognize where we left our things and you don't recognize any of the men. You are further confused when I give a broad wiggle of my hips and then turn with a sweeping arm as I present you.

"Surprise, Penny m'love! I've brought yummy goodies to share you with and to show you off to!"

You're sputtering, half angrily and half in protest but the men are jogging up and you don't want to make a scene. You're determined to have it out with me as soon as we're alone though. I see the look in your eye but I'm not worried, I know that you're going to enjoy today...in spite of yourself. Wrapping my arm around your neck I pull you in for a deep kiss, sliding my fingers across your still tender pussy as a reminder why I'm in your life. You moan with pleasure into my mouth and I stroke you more firmly, ignoring the men for a moment until the older man clears his throat with a chuckle.

"Oh all right," I say with mock irritation. "I suppose you want to be introduced?!!"

"It'd be nice."

His voice is pleasant and he looks at you closely, causing you to blush. In fact all the men seem to be quite observant you notice and you shift, trying to move behind me. I step to one side so I can introduce you.

"Penny, this is a very dear friend of mine. Someone I've known most of my life, Thomas, but Tom, I don't know these other gentlemen."

"Well, you said you wanted someone who could swim and had stamina, so I brought a couple of my fellow Rangers..."

I interrupt, "Wait! I thought all you Rangers jump out of planes?"

One of the young men looks at me, without smiling, but with a definite twinkle in his eyes he replies, "Sometimes we jump over water, ma'am."

"TomCat, tell him if he calls me ma'am again, I WILL hurt him!"

"Well, you will TRY anyway," turning to Chase, "but her name is Ali. You should probably try to remember it." He's laughing.

"Fuck you!"

"You have already!"

By now everyone is chuckling at our interaction including you.

I sweep my long ponytail back over my shoulder huffing as I pretend indignation, "And this is Penny. She's a little uncomfortable at nude beaches and around strangers so be gentle with her fellas. Not too gentle, mind you, but, you know...."

Tom introduces his fellow Rangers as Cash and Mike and we head back to our site. The men fill us in on all of the extra coolers of food, and drinks they have brought as well as a small grill and some more blankets which they've already spread. There's plenty of room now for five bodies and any of the various ways they might fit together today. I try not to rub my hands together with glee but I'm really looking forward to it. I suggest that we all need sunscreen and Tom grabs a bottle of lotion, pulling me down to the blanket. You look at me helplessly, begging for rescue as Cash and Mike take it on themselves to make sure you are well covered, one taking your front and one your backside and both sporting full erections. I can feel Tom's hard on nestled between my ass cheeks where I sit, his legs are on either side of me and he is slowly covering my back and shoulders with the lotion.

"Feels good, TC. You've always had good hands...and great lips."

I turn my head to steal a kiss.

"Before the day is over I'm going to wrap them around your tits and clit too."

"Mmmm. Hands or lips?"

"Whichever you prefer, or both preferably, right before I make you squirt in front of the kids... Does your Penny know your little trick?"

"No, not yet, but today is supposed to be for her!"

"Oh, she'll get hers too. I definitely want to fuck her after all you've told me. But I'm not passing up any opportunity to fuck you again either."

"Sweet man! You always say the nicest things. When you aren't correcting my grammar, or telling me what poor choices I've made with the men in my life -- present company excepted of course."

He laughs, "Of course! If you turn around I can do your front now."

"Can I trust you not to make an event out of it?"

"When haven't I been trustworthy...at least where you're concerned?"

"Tru' dat!"

I turn to face him and he grins at me.

"Decisions, decisions...where to start?"

We both laugh and I turn to see how you're doing. You've blushed clear to your toes again. Mike is taking his time covering your sweet ass with the lotion. His hands are covered with the cream and he is making lingering circles around the globes of your buttocks, his thumbs sliding into the crack of your ass and sliding down and around until he can slide his fingertips into the crease between your thighs and your butt, before starting over again. Cash meanwhile is sliding his lotion covered hands from your shoulders down and around the sides of your breasts, across the sensitive skin below each breast and then back up over the top and nipple, making sure to tweak and pinch each nipple in passing. He then slides his big hands firmly down and over your belly to your thighs, not actually touching your sex but sliding his slick hands up to the top of your inner thighs and then across each fold where leg meets belly. You are pressing your lips firmly together and I suspect that, despite the blushes, you are trying hard not to moan with pleasure.

Thomas slides me around again so that we can both watch, but while we're watching his arms come around me. One hand is cupped to cradle a breast and tease the nipple -- the other is cupped to cradle my cunt. He nibbles my ear sending a shiver down my spine and instructs me to grab some towels. I know what's coming now and I lean back against him in anticipation. He cups my sex in his big hand, feeling the sudden flow in my juices as my excitement builds. He slides his hand back and forth over me a time or two until his hand is nearly as wet as my pussy. Sliding his middle two fingers into my slit he begins to tease me, knowing how close my G-spot is to the mouth of my cunt, and knowing from experience how much pressure to exert. I've been excited for hours now and his touch is like heat lightning against me.

"Oh FUCK, Tommy I'm gonna cum!!!"

I try to clamp my legs around his hand, the pleasure is so intense this way, but 'not yet' he commands. With his other hand he is pulling and twisting at a captive nipple and I realize that all other activity has slowed in order to watch us. Mike and Cash are still stroking and pressing against you, but now they're focusing more on your own ass and pussy. There is a hand pressed firmly against your bottom and I imagine that one or more fingers are possibly embedded in your sweet ass, while similar action is taking place in your cunt.

My legs are trembling with the need to close them, so I bend my knees and pull them toward me, wrapping my arms behind my knees to keep them open wide. I'm feeling a tremendous pressure building and a need to bear down while multiple mini orgasms roll over me. Finally, having teased me enough you press down on my swollen clit with the heel of your hand. Rubbing and exerting pressure on my clit while you are doing the same to my G-spot sends me hurtling over the edge and with a long, wailing cry a gush of fluid bursts from my pussy, reaching almost to my knees.

"Please!!!" I scream but Tom mutters 'not yet' and continues to press and rub me. My back arches against him, my teeth are buried in my bottom lip so hard I think I taste blood. Another wave hits me and another gush of fluid wets the towels between my legs, and then another. A fourth orgasm surges from me and I am gasping for breath and sobbing.

"Please," I beg. "I can't..."

"Stop, please..." Penny, your soft voice makes Tom lift his head, turning to look at you while I continue to weep, trying to catch my breath. "No more," you add, "Now you're just torturing her."

Tom wraps a spare blanket around my shoulders and lays me down, curled on my side. He kisses me gently on my cheek before getting up and going to you.

"I would never, NEVER torture Ali, Penny. I do enjoy giving her more pleasure than she can handle at times."

Cash and Mike have stepped aside, making way for their senior. Tom reaches out and I realize how well matched all three men are. Despite your height, Tom is taller, as are his young Rangers. He is, the three men all are, strong, obviously fit and active -- well muscled men. Tom's large hands cup your delicious breasts, hefting them as if to test their weight, before wrapping his fingers around your nipples.

"I'm going to enjoy giving YOU more pleasure than you can handle today too," he tells you.

Your eyes widen and you blush but your nipples crinkle and I see the pink tip of your tongue tracing your top lip.

"I...I'm married. I can't...I mean, won't..." you protest stammering and blushing again.

Ignoring you Thomas continues to twist and tease your nipples while I regain my strength. Not to mention my ongoing interest in the day's activities.

"Ahem," I clear my throat and announce, "Gentlemen, I think it's time for you to get our girl wet." I say, looking meaningfully at the incoming waves.

Murmurs of 'yes, ma'am' and 'good idea' greet my suggestion although you toss me a look of betrayal as the three men begin taking you down to the water. I lever myself to my feet and follow behind feeling a need for a little cool down and splash off myself. As we reach waist deep water the younger men dive in and leave us briefly, swimming out to deeper water before heading back in to rejoin us. Meanwhile Tom and I cuddle close to you. He is facing you for now and pulls you close, hands firmly gripping your hips below the waterline. Behind you I am reaching around, cupping those delicious double DDs that I'm so fond of suckling at. I'm pinching and rubbing each of your nipples -- dragging the hard tips across Tom's chest -- while I nibble and nuzzle at your neck and shoulders.