Jennifer's Jamaican Weekend


My Dearest Jennifer,

I think it’s time we took a little vacation again, especially now that it’s so cold and snowy here. Rather than just another shopping trip to the mall, I have some place a little farther south in mind.

Braving the snow at O’Hare, we finally board a 767 for a non-stop flight for Montego Bay, Jamaica. Reclining our First Class seats after take off, we settle back for a relaxing few hours. In the overhead bins are our carry on bags so we will not be long detained at our destination. My suit case contains two bags, a traditional, red, 2 quart bag with a standard douche nozzle, and a 3 quart clear vinyl bag from Beth Tyler with one of her special green nozzles. I wonder for a moment if there would be an opportunity here on the plane ? Probably not.

After a delicious snack, and glass of Merlot, we snuggle down in the seats as if to take a nap while the other passengers watch the movie. Covering you with the gray blanket, I manage to keep my hand covered as well. Reaching down just a little, I pull up the hem of your skirt, letting my fingers glide along the smooth inner surface of your thigh. Parting your thong bikini panties, I run my fingers through the fine hairs of your love triangle, and probing a little more, my fingertip glides down your silken valley, already moist and slippery. Resting the ball of my fingertip at your entrance, I feel you squirm a little in the seat and turn slightly towards me, to allow me free access your charms.

Wetting my finger with your essence, I move down and spread the slick fluid around your crinkled rosebud. Resting there a moment, I feel you squeezing your opening, flexing, seemingly trying to draw my finger inside your dark portal. Yes, I would like that too, but I have a little something special for you this time. Reaching down beside me, I pull up my coat and digging into the large pocket, and pull out a small 4oz bulb syringe with a child’s enema tip. I was half afraid I was going to be a problem at airport security this morning. Afraid of how I was going to explain my need for this little enema bulb filled with wine!

I see the surprise on your face as you quickly realize my intentions. My hand snakes under the blanket once more, bulb in hand. Resting the full bulb against your thigh, I again dip my finger into your now thoroughly moistened valley. Coating my finger, I transfer the slick juice to your rosebud, and slowly insert my finger to the first knuckle, pushing the slippery substance inside your tight passage.

Removing my finger, I pick up the little bulb and steer the small nozzle by feel to your crinkled orifice. With a slight twisting motion the nozzle glides in as far as it will go. Your eyes now wide with anticipation, I slowly squeeze the bulb until the entire contents jet into your rectum. Holding the bulb tightly, I gently pull it out, and discretely discard the used bulb in the seat back. Wonder what the aircraft cleaners will think of that!

“No, I used some of that Mad Dog 20-20 that your brother left last month. It wasn’t fit to drink, but it was fortified, and I thought it might be just the thing.”

“Besides, with a cabin altitude of 8500 feet, it should go to work pretty quickly, and rather well, too.” Just then, the Fasten Seat Belt light comes on, ending any thought of expelling the enema anytime soon. I guess you are glad that you are not trying to hold two quarts!

When finally we are free to move about the cabin, and you stand to go to the lav, it takes a few tries just to get up. It seems that the small wine enema has given you quite a buzz. Perhaps we will have to try that again.

In another hour we start our descent into Montego Bay where I have made reservations at the Doctor’s Cove Hotel, right on the beach. After clearing customs and obtaining a rental car, we drive the short distance to the hotel. When we have checked into a nice room on the second floor facing the water, I suggest we take a drive while the sun is still well up in the sky. I go downstairs to arrange a picnic basket while you continue to unpack.

“There is a place not too far from here, an old Great House, where they have a nice picnic spot in the back. I think you will enjoy what I have in mind.”

Grabbing the picnic basket and my haversack, we walk across the street to the car and start out. After a short drive on the “wrong” side of the road along the north shore, we come to Rose Hall, and turn up the long drive. Rather than stopping in the front, I continue along the drive about 1/4 mile to a secluded glen of tropical hardwoods encircling a pool of crystal clear water fed by a splashing waterfall. Stopping the car, we spread an old blanket on the lush grass by the water’s edge. “Let’s go for a quick dip in the water Jennifer, this tropical heat is quite a change from the snow of home.”

Quickly shedding our clothes, we wade into the cool water, our bare feet cushioned by the white sand on the bottom. After a short time we return to the blanket. I think it is time for your first open air enema. “OK, Jennifer, please turn over and get up on your knees, with your head down on the blanket.”

The sight of your raised cheeks causes my member to swell with anticipation as I savor the luscious view. Reaching into my haversack, I pull out my trusty two quart enema bag with the large ribbed nozzle you seem to like so much. Taking the small tube of Vaseline, I squeeze a liberal amount on my finger. With one hand spreading your firm cheeks, I bare your crinkled rosebud to the harsh sunlight, and center my finger on your tight opening.

Coating the brown orifice, my finger slowly slips inside to the first knuckle. Pulling out again, I take the tube and squeeze more Vaseline directly onto your rosebud. With a pushing motion, I gently drive the Vaseline deeper inside you until finally my whole finger is tightly wedged in your passage. Back and forth, my finger moves, lubricating your rectum completely. The sight of my finger buried in your dark tunnel, and the slick feeling have caused my shaft to swell with anticipation of what is to come.

Standing up, I dip the bag into the pool, filling it with the crystal clear water. Releasing the clamp for a moment to let the air out, I again kneel behind you, bag in hand. Spreading your cheeks once more, I center the large green nozzle on your glistening rosebud. With a twisting motion, I slowly push the nozzle in, until the largest diameter has passed your sphincter, when the nozzle seems to seat itself without further assistance from me. As you adjust to this new invasion, your velvet lips spread a little, revealing the dripping interior of your silken valley. My now throbbing member aches to be buried deeply inside that inviting passage.

Holding the full bag in one hand, I release the clamp and see the hose stiffen with the flow of cool water as it begins it’s journey into the deepest part of your bowels. I hear you moan softly with pleasure as the water starts to fill your rectum. It certainly does seem to concentrate your attention like nothing else!

The delightful sight of you in the sun, with the long red tube jutting from between your cheeks causes my shaft to dry throb with desire. Moving directly behind you, I hold the bag on my shoulder, and place the swollen head of my engorged member at the entrance to your love tunnel. With a slight movement of my hips, the purple plum begins to part your pink lips as it glides into your hot passage. As the bag continues to fill you with it’s cool cargo, I stroke slowly in and out. What a view! I can see my shaft, coated with your slick essence as I pull out, while at the same time, I see the end of the green nozzle jump about of it’s own accord with your contractions.

Reaching around your waist, I can feel the swelling of your belly as the water continues to fill your bowels. “Oh, I can feel your fullness my dear Jennifer, as the water spreads inside you, and I know just how you feel as the pressure mounts. But what a delightful way to wash out that wine!”

Finally the bag empties with a gurgle and I reclamp the hose. Letting the bag fall to the ground, I grab your waist and pull you tightly against my loins as I feel the onset of your first orgasm. Without moving, I wait patiently as you begin a series of rhythmic contractions, enhanced by the need to hold your enema. Finally, with a sigh of contentment, I feel you relax a little and slowly withdraw my rigid shaft. With a gentle, steady pull, the nozzle slides out with a small plop.

“You can go behind those trees over there, and then wash in the stream that exits from the pool. I will refill the bag while you are gone.”

By the time you have returned, I have refilled the bag and left it to warm in the sun. Opening the wicker basket, I take out two wine glasses, and pour us some of the thick red wine the hotel has provided.

Sipping the wine, I ask you if you would like an underwater enema. Well, I have never heard of one either, but it might be fun. You lay down on your side, with one leg drawn up to your coral tipped breasts while you enjoy the wine. Setting my glass down for the moment, I spread more Vaseline on my finger and begin to massage your rosebud, pushing more inside you as well. When your rectum is well lubricated, I take the nozzle and slowly push it inside you. I meet the same initial resistance as before, followed by the last few inches of the nozzle slipping in as the widest part passes your sphincter. The knob certainly helps prevent the nozzle from slipping out on it’s own accord.

Standing up, I offer you my hand, and pull you up too. Holding the bag in my hand, the trailing hose firmly embedded inside your rectum, we walk to the pool and into the water. When the water is about four feet deep, I tell you to float on your back while I hold your feet around my waist. When you are comfortable, your hair floating on the water, your arms at your sides, I hold the bag over my head and release the clamp. Once more the hose stiffens with the renewed flow of water, this time rather warm from the sun’s rays. I watch your expression of surprise as the first surge of warm water hits your rectum. It is a nice contrast between the cool water of the pool surrounding you, and the relentless intrusion of the warm enema.

“My Dear, I seems that you are enjoying the experience. How does it feel to be so covered in water, both inside and out?” Even in the cool water, my instrument remains rigid at the sight of you there in the water, with the tube snaking from between your legs to the bag over my head, knowing full well the feelings you are having as the pressure builds.

From time to time, I feel your legs grip me a little tighter as a wave of pleasure passes over you. Your nipples stand out proudly, either from the cool water, or your rising passion as the enema continues to flow, filling your bowels with the warm water.

After a while the bag finally empties, and I reclamp the hose, leaving the nozzle embedded inside you for the moment. Letting the empty bag float on the water, I reach forward and run my fingers through your fine hairs and across the soft skin of your thighs. Walking back a little into shallow water, I let your feet rest on the white sandy bottom, while I move around to one side. I enjoy the sight of you laying there in the water, your swollen belly breaking the surface as I imagine the water swirling around inside your bowels. Reaching down, I take one of your erect nipples between my fingers and roll it back and forth. You are constantly being assaulted by erotic sensations, the stimulation of my fingers and the fullness of your retained enema. To enhance your pleasure, I stroke your satin valley, moving the ball of my finger over your little man. Not rubbing, but letting the motion of my finger gently rock him from side to side. Taking your hand in mine, I pull you upright again, and lead you out of the water, the hose trailing you as we return to the blanket. Once again, I ask you to get on your knees.

Moving around behind you, I can see that your arousal has caused your lips to swell with passion, and your sweet portal to gape open in expectation of receiving my rigid shaft. I also see the nozzle still firmly embedded. With a steady pull, I slide the nozzle from your tight grip and set it aside. Before I can return to my desire to impale you with my throbbing member, you ask me if you can give me an enema while retaining yours. Do I have to answer!

Laying down on the blanket, I watch you quickly fill the bag from the pool, and without delay, apply the slick Vaseline to my own dark passage. It feels so good as your finger lubricates my passage, and when the nozzle is slid inside me, I almost shoot on the spot. Holding the bag high above your head, I feel that rush of cool water explode inside me, concentrating all attention on my loins. My rigid shaft points at the sky and quivers a little with the level of my excitement.

As the water begins to fill my bowels, your free hand applies more Vaseline to my shaft. The warm grip of your hand causes me to ask you to stop for a moment until the dry throbbing stops. Rather than just letting go, your delicate fingers encircle my shaft at the base and cause me to momentarily forget the flooding of my rectum. When the bag is empty, you clamp the hose and slowly remove the nozzle.

Moving to the edge of the blanket, you once again get on your knees, your head on the blanket, and tell me to quickly enter your flooded passage. Moving around you on the grass, I guide the well lubricated head of my shaft to your crinkled opening, clenched tightly to hold your enema. I find I must also squeeze my cheeks to retain my own enema. Holding your cheeks apart, I slowly push against your opening, feeling some resistance at first, but the Vaseline coating my shaft, and the lubrication from your enema, allow me entrance. Oh, what a delightful friction as I slide deeper into that exquisite passage. As I am about half way in, the head of my shaft touches that pool of warm water you have been holding inside you. Reaching around your hips, I pull you back tightly against me. Pausing for a moment, I glory in the feeling of being inside you, bathed in the warm water, and feeling your contractions as you strain to contain your enema.

As I start to pull back, I watch my glossy shaft emerge from your stretched rectum, and am able to reach between us to stroke your dripping passage. Moving my hand around your waist once again, I find that I can slide my finger down your slick valley as I plunge deeply into your rectum. When my finger stops on your little nubbin and starts to flutter back and forth, I feel your cheeks clench with tension as you start on that erotic journey to a massive orgasm. You are filled with both your enema and my rigid pole, and that combination, as well as my finger on your little man, serve to push you over the edge.

With a loud cry, your first orgasmic contraction grips my shaft all along it’s length, squeezing me in a silken vice. Your spasm triggers an explosion of hot sperm from my shaft, flooding your bowels with a second enema. My eyes close, I feel turned inside out as I try and plunge deeper into your hot rectum. Your second shuddering orgasm causes me to lose all control, and a gusher of water shoots forth from my uncontrollable sphincter. With each jet of water massaging my prostate, another jet of my hot essence floods your rectum, momentarily stopping my expulsion. I can not control the experience, only ride the waves of delirious ecstasy as each ejaculation causes you to contract your internal grip. It seems like the cycle goes on forever, and I can barely hold on to your writhing hips as I feel my very essence being sucked from my loins. I don’t know if we were loud or not.

Finally, I collapse beside you, my head by your shoulder, as you also finally lose control of your sphincter and flood the lush grass with your expulsion.

We lay there for a while without moving, my arm around your shoulder, recovering from our massive orgasmic experience. The only sound is that of gushing water now and then as we expel the last of our enemas onto the grass. Finally, as the tropical sun continues to beat down on our backs, I suggest we clean up in the stream, and then go for a long swim in the pool.

Perhaps we will go to some clubs tonight, or maybe a slow enema on the balcony as the sun sets over the bay…