Ann’s Fantasy


I had met Ann through friends. We met almost six months ago and now she was coming back for a visit. Ann and I had carried on an intriguing relationship in emails, instant messaging and regular mail. We also managed some precious time together during a short business trip. I was drawn to Ann for her warmth and sensuality and drawn to please her as well.

I had been out on the trails for a few days enjoying the summer nights and here I was, cleaning and repairing and, more importantly, waiting for Ann. Ann and I had explored many things in our conversations, from politics to our sexual interests. We had both been fascinated with our reading of “The Story of O”. For me, it was my first serious erotic reading during my college days. Ann shared with me that she was a submissive and became very aroused whenever we spoke of her fantasies. I had a challenge before me. Ann had asked me to create an experience for her during her visit. She asked me not to tell her anything. I had no experience with this, but was willing to give my lovely lady friend a special gift.

Since I had no experience in the proper treatment of a submissive, I called on a very experienced acquaintance. Jackie and I had met in a conservation workshop and immediately became friends. She was openly bisexual and an intelligent natural sort. Jackie was eager to help, but only after she calmed her laughing.

“Boo, you with a sub? That’s too much!”

It was something Jackie had seen in my character and in an entire night of intimate conversation in her small cabin. She agreed to help me make a day that Ann would remember and eagerly volunteered the services of her lover, Lynn, as well.

Visitors chuckle at our single gate airport, but it’s all we have. I saw Ann step down the stairs of the small commuter aircraft. She almost ran to my arms and I was treated to the warm scent of sandalwood mixed with warm woman scent.
We picked up her bags and headed to my truck. As I helped her up the tube step, she asked, “What do you have in store for me, Boo?” I simply smiled.

“Were you surprised, Boo?”

“Yes, Ann, but be warned. Boo has left for a few days. My name is ‘Jaeger’. You will address me as ‘Sir’, ‘Jaeger’, or ‘Master’. Understand?”

“Yes”, replied Ann as her eyes and head dropped toward her lap. I swung my truck around and headed out of the airport with the heavy treads of the four-by-four beginning to whine on the asphalt. I glanced over to Ann. Her head remained down, her hands folded in her lap.


“Yes, sir”, came her quick reply.

“Reach in the glove box. You will find some sunglasses. Put them on. Now!”

She reached in and found the prepared glacier glasses and put them on.

“I cannot see, Master”. I had taped the lenses over with black plastic tape. The blacked out lenses, in addition to the solid side shields of the glasses, reduced Ann’s view. She could now only see what light and images came in at the very top and bottom of the lenses.

We had driven about a mile and pulled up to a four-way stop.

“Remove your shoes, slacks and panties”, I ordered.

“But, Boo…I mean Jaeger…”

“Boo is not here, Ann. Do not make that mistake again! Take them off now!”

I watched Ann lean forward and remover her shoes. She then lifted herself off the seat. She had such nice taste in clothes. Her linen slacks came next quickly followed by her ivory colored lace panties. She gathered her clothes and folded them neatly with her hands coming to rest again folded in her lap over the juncture of her thighs. Ann was beautiful. A womanly princess.

My mind said, “Forget this domination thing, take her to your place.” The lovely Ann, memories of two nights of passion, and her present partial nakedness tempted me.

“Where are we going, sir?”

“That is my concern”, came my stern reply.

We drove on. Twenty-two miles later, I pulled onto a twisting gravel road, stones pinging in the wheel wells as the lugged tires plucked them from the surface. Another turn and we were on a soft fire trail, the noise dying. The smell of pine filled the cab. We turned through a gated fence onto a drive leading to a small cabin and stopped. Jackie quickly came to the door, a broad smile and excited wave greeting me.

“Where are we, master?” I did not answer.

“Get out of the truck, Ann. Now!”

Ann opened the door, struggled a bit finding her footing on the tube step and her bare feet landed in the pine straw.

“Stay here”, I said as I moved toward Jackie on her small wooden porch. We hugged and I felt Jackie’s warm, full body against me. We spoke in whispers although we were a good distance from Ann and the truck.

“She’s beautiful, Boo!” came Jackie’s first appraisal. We both looked back at Ann. Her light brown hair falling easily on her shoulders. Her upper body covered by a silk blouse. The blouse covered her only to the top of her well-shaped hips. Her legs were a perfect match for her body. There she stood, shifting a bit on the warm straw and her light skin contrasted against the cool, dark green of the forest and the dark Ümraniye Escort shininess of my truck. Her hands remained folded over her sex. It was a remarkable sight.

“Are you ready, Jackie?”

“Oh yes, I hardly slept last night.” With that, Jackie grinned and pulled her shirt back exposing her hard-nippled left breast. We both laughed quietly.

“Let’s introduce you to my lovely Annie.”

Ann’s head came up as we moved toward her.

“I have a friend with me Annie. She is called ‘Leaf’. You will trust her as you trust me. Understand?”

“Yes, master.” Leaf stepped forward, grinned up at me and suggestively licked her lips. Jackie was not beautiful, but rather one of those ladies I call “handsome”. She had the angelic face of a happy cherub framed by her practical short brown hair.

Leaf ran her fingers along both side of Ann’s face, travelling down along both sides of her throat. Ann started but controlled herself. Leaf began with the first button. Ann’s hands came up and Leaf slapped them, batting them away. Ann folded them again at the top of her thighs.

“That’s better my little friend”, sneered Leaf. Again, she flashed me a grin. Leaf would enjoy this.

Another button, another, and the blouse was slipped off her shoulders. One unusual thing about my Annie was the tattoo of a cat on her lower belly. A beautiful cat and, again like all things about Ann, tastefully done. Leaf nodded her approval of Ann’s body and the classy ivory colored bra protecting Ann’s breasts.

Leaf opened the front clasp and Ann’s breasts dropped slightly. Like the rest of Ann, they were beautiful as well. Her nipples were puffy and inviting. Leaf took both nipples between thumb and forefinger then lifted the weight of Ann’s tits upward. Ann twitched slightly from the shock of a strangers hands and the sensation of having the weight of her breasts supported by her stretched nipples. She controlled herself and did not move, but a low moan escaped her lips. Leaf released her nipples and moved around Ann to the open door of my truck. She ran her hand across the seat.

“Jaeger, your lovely little slut got your seat wet! That is inexcusable. Did you pee on master’s pretty truck? Did you? Did you?”

Ann, surprised by Leaf’s harsh tone quietly answered, “No, I didn’t.”

“Well, what’s this wet stuff? Well?” demanded Leaf giving little time for Ann to answer.

“I don’t know. I really don’t know what it is.”

Leaf moved again to the truck. “There’s only one way to check this.”

Leaf ran her finger across the seat and put it to her lips. “Jaeger, this is pussy juice. She’s turned on. She probably came on your seat! Did you cum, little Annie? Did little Annie come in master’s truck? Did Jaeger tell you to cum?”

“No, I didn’t do that”, protested Ann. Leaf ran her finger across the wetness on the seat once more.

“Then tell me what this is if it isn’t girl cum, Annie”, demanded Leaf as she pushed her finger between Ann’s lips.

“What is it, Ann?”

“It’s from me, Leaf”, came the whispered answer.

“What? What did you say? Say it louder so Jaeger can hear.”

“It’s from me. I had an orgasm. I couldn’t help it. The thought of being so close to master was too much.”

Leaf’s response came quickly. “Master, this is not acceptable. I need to take Ann inside. She needs to understand there are consequences for bad behavior. Oh. Jaeger, look. Look at my finger! It has lipstick on it. Did you instruct Miss Annie to wear makeup?”

“No, I did not Leaf. She is certainly taking liberties with my rules.”

“I think you’re right master. She is taking liberties.” With that, Leaf pulled a pair of padded cuffs from her back pockets. She quickly had them fastened to Ann’s wrists. Leaf reached into the truck, grabbed Ann’s clothing and thrust them at her. “Carry these!”

“Where are you taking me?” pleaded Ann. I think I heard genuine concern in her voice.

“Just follow me”, came Leaf’s terse reply.

Leaf led Ann into her comfortable cabin. An oasis of warmth in the often cold north woods. I followed. I loved Jackie’s place. She was a home grown girl talented in quilting, furniture refinishing and folk painting. I could spend hours at her place. A river stone fireplace and walls adorned with hanging quilts and art. She had only two rooms. A bath and an open bedroom, living room, kitchen combination. The rustic simplicity was beautiful in itself.

Leaf led Ann firmly. She stopped next to the rustic four poster bed and removed the last article of Ann’s clothing pulling the blouse over the soft but sturdy cuffs. Ann’s eyes remained covered by the glacier glasses. She would love this room…if she could see it.

Leaf pushed her back onto the bed and pulled Ann’s hands above her head. One then the other strap from the cuffs fastened quickly around the posts. “Open your legs, little Annie”, came Leaf’s mocking voice. Ann didn’t move.

Time for Jaeger. “Ann, open your legs now! Leaf is very kind and patient compared to another friend who will join us shortly. Now, Annie!”

Ann’s legs Anadolu yakası Escort opened. Leaf looked at Ann’s open womanhood as she secured her ankles to the bottom posts. She moved forward and tugged gently at the small tuft of hair Ann neatly maintained at the top of her cleft. Ann pulled her hips to one side to avoid Leaf’s investigations.

“We can make that disappear, Annie”, warned Leaf. I shook my head signaling a ‘no’ to Jackie. She thrust out her bottom lip in a mock pout. She was a tease! She bent forward and kissed Ann’s outer lips and ran her tongue along her belly glancing back and giving me her playful smile. Leaf licked Ann’s kitty tattoo as well then dwelled on her navel, drilling it with her tongue. Ann moved with a quiet moan making its escape from her lips.

I motioned for Jackie to join me at the kitchen table. She rose from the bed with another pout. This one less than a mock pout. I noticed Ann’s head moving, trying to catch a glimpse of her tormentor through the small gap at the bottom of the glasses.

“We need a blindfold, Jackie”, I whispered.

“You think I’m not prepared, Boo? Shame!” she said giving my cock a squeeze then moving to the antique trunk at the foot of her bed. She rummaged around a bit then pulled a dark blindfold out waving it over her head in a flourish.

“Close your eyes very tightly, Annie”, Leaf commanded. She quickly removed Ann’s glasses and replaced them with the blindfold blocking Ann’s view completely. Leaf smiled at me and straddled Ann’s belly with her lovely rear towards Ann’s face. She laid her fingers on each of Ann’s lips and spread her open.

“Ohhhh! What have we here? Oh Jaeger, we don’t have to go to the ocean to find a pearl. I have found a beauty here! Master Jaeger, may I have a bit of a snack before Ash arrives?”

“Sure Leaf, but take your time and make sure that lovely pearl is properly polished with your tongue.” Leaf turned around, curling up between Ann’s legs and partook of her snack. She ate with an increasing tempo. Lapping, slurping, and holding Ann open to her. Ann began to move, but was still maintaining some control. Leaf sat up and removed her own shirt, wiggling her breasts at me in a tease she knew pleased me. She went back to Ann, but Ann suddenly thrust her hips upward into Leaf’s mouth and lips.

“Stop! Leaf, you’ve eaten enough.”

“Oh, Jaeger please! A little more, please?” came a sincerely pleading voice from Leaf. What had begun as a play had gone beyond. She wanted my little Annie.

“I’m hungry, Leaf. Come here and fix us something.” Ann heard my request to Leaf and sighed deeply as she felt Leaf’s weight lift from the bed. I was surprised she remained still after Leaf’s dedicated ministrations.

Leaf had a request. “One more thing, Jaeger. I need to check one more thing. Please!”, implored Leaf.

“What do you need to do, Leaf? Just be quick.”

“I need to check the hardness of my nipples”, came the reply…and grin. Leaf bent down over Ann and took her left breast guiding the nipple between Ann’s moistening cleft. She did the same with her right breast and nipple. Leaf rose and came to the table where I was now seated. She held both breasts up to me and the shiny wet nipples stared at me.

“Master Jaeger, do you think they are hard enough?”

“They’re just perfect, Leaf.” She smiled and offered one wet nipple to my lips and pulled her other breast upward, taking her nipple into her mouth savoring again the essence of Ann. As did I.

“She’s really turned on”, Jackie whispered as she laid a small plate of cheese, mild sausage, fruit, and homemade bread before me. I nodded. We looked over and Ann moved. Her hips occasionally coming off the bed as she made little guttural noises attempting to distract us. Shameful.

“Quiet and lie still!” I shouted tearing off a piece of Jackie’s loaf.

“Are you hungry little Annie? Maybe thirsty?” asked Leaf.

“Yes, I am.” Leaf filled the glass with cool artesian well water and took a straw with her. She lifted Ann’s head as Ann drained half the large glass.

“Something to eat, little Annie?

“Yes”, came the reply.

“Would you care for some fruit my dear?” A suspiciously overly polite query from Leaf.

“Yes, please. I’m hungry.” Leaf returned to the kitchen table and picked up her wicker fruit basket. She broke a banana free from its mates and returned to the bed.

“I have a banana for you, sweet Annie. I’ll peel it for you.” The white inside of the banana emerged along with its sweet fragrance. Leaf knelt between Ann’s open thighs and spread her pink petals to the sides.

Ann protested, “No! Stop!”, as the banana slid in. Another grin over the shoulder from Leaf. She moved the fruit in and out a few times and withdrew her fruit dildo slowly.

“Ummmm, creamy slut is the flavor of the day Master Jaeger!”

“Leaf. Ann is hungry, feed her now”, I scolded Leaf.

“Perhaps she should learn to eat from Jaeger’s loving hand”, quipped Leaf. I walked to the bed as Leaf returned the banana to Ann’s warm home and was gently thrusting İstanbul Escort it in and out. As I neared, she released the banana leaving it half enveloped by Ann. I reached out my hand and slid the warmed, slick fruit from Ann. She sighed quietly.

“Feed me, sir. Please feed me”, implored my compliant Ann.

“You are doing quite well, Annie. I am beginning to be pleased by your obedience. I have this luscious, sweet reward for you”, I said as I moved the banana to her lips.

“Open your mouth and I will feed you.” Ann did as she was told. Her inviting mouth opened and she tasted the banana slick with her excitement. She began to eat.

“Thank you, Master Jaeger. Thank you.”

“Eat the rest. You will need your strength”, I cautioned. As Ann ate, Leaf took advantage of Ann’s spread legs. She quickly pulled off her jeans and lowered her lips to Ann’s pussy. She was back at it. Lapping the wetness with her flattened tongue, occasionally taking Ann’s clit and inner lips between her teeth and gently pulling. Ann began thrusting again.

“Master, I’m going to come!”

“No, Annie, you may not cum and you may not move.”

“Then make her stop, sir. She is sucking so hard. Please make her stop! I want to please you, Master. Only you.”

“Alright, precious. Leaf!” Leaf looked toward me repeating her sly smile and pout. She stood up at the side of the bed and pointed toward the window. I saw Lynn’s silver Suburban gliding to a stop in the soft dirt. Lynn and Jackie had been lovers for years and Lynn had eagerly agreed to lend her talents to our experience with Ann.

The lovely raven haired Lynn strode confidently to the door of the cabin with her nylon bag casually slung over her shoulder. Her heels sounded heavy on the wooden porch. Through the door she came and became ‘Ash’. Ash joined her playmate Leaf and Master Jaeger.

“Who’s here?”, came Ann’s inquiry.

“Our friend Ash has joined us. She is already admiring your beautiful and open body.”

“Would you still like to cum?” I asked.

“Yes, but only for you, master. Just for you.”

“Very good, Annie. That is the answer I was hoping for. The answer I wanted. I will allow you to cum many times later, but remember you weren’t a very good girl on our trip here. Remember, Annie? Remember your excitement and my wet seat?”

“Yes, Jaeger. I’m sorry. What can I do to make you happy with me?”

“Ash will help you make things right.” I looked to Ash. She smiled and moved toward the bed.

“Jaeger, your pretty slut is wearing lipstick!” said Ash.

“Yes, Ash, Leaf noticed that too. Could you help her remove it?”

“Yes, Jaeger, but I’ll have to use my pussy to wash it off her lips. Will that be acceptable?”

“Of course, Ash.” Ann could hear Ash’s boots unzip followed by the sound of tight fabric sliding down taut thighs.

“No, Jaeger. I don’t want her to do that!” protested Ann.

“Annie, do you wish to please me?”

“Yes, Jaeger. You know my heart. Anything for you.”

“Good girl. I have a gift for you. You will see the beauty of Ash and Leaf. Leaf, take her blindfold off. I wanted her to see the soft instruments of her sensuous torture. Ann blinked getting used to the soft light of the cabin.

“Do you like my playmates, Ann?”

“Yes. They’re pretty, Jaeger.”

“Good, Anne. Very good.”

“Time to get cleaned up”, said Ash as she moved toward Ann. She leaned over and kissed her deeply. “Yes, the lipstick is still there. We have to clean that off.” With that, Ash quickly straddled Ann’s head bringing her shaved pussy in contact with Ann’s lips.

Ash began to move back and forth across her lips. “Kiss me. Kiss me. Lick your lips and wipe that lipstick on my cunt, slut! You’re not doing enough! Leaf, little Annie needs some motivation. Leaf pulled out the three fingers she had buried in her own pussy and moved between Ann’s legs. She was licking and sucking quickly and returning her own fingers to the wet warmth between her own legs.

The scene before me was having its effect. I was very hard. I wanted to ask Leaf and Ash to leave. I wanted to take my lovely Annie right then, but more than that I wanted her fantasy complete.

“Leaf, please taste Ann’s lips and see if the lipstick has been properly removed.”

“Of course, Jaeger.” Ash moved up from Ann’s face as Leaf moved around her and bent licking Ann’s lips and cheeks gathering Ash’s wetness.

“Mmmm. I think it’s gone. All I can taste is your slut’s lovely mouth and Ash’s juices.”

“Fine, thank you, Leaf. Ash, I’m not sure Ann is ready for my cock. Do you have anything we could use to prepare her?”

“Of course, Jaeger.” Ash moved to her bag resting on the table in front of me. She removed a leather-covered box and opened it. Her hand caressed one of her favorite toys. She carried it toward Ann. Ann’s eyes widened as she saw the electrical plug dangling from Ash’s hand.

“Leaf, plug this in for me.” Leaf bounded over and plugged the power cord from Ash’s violet wand into the outlet. A flick of the switch and the device came to life with a quiet hum. Ash had fitted the mushroom tip on the wand and ran the device over her own nipples as she adjusted the intensity. The wand created its pretty violet sparks in a perfect circle following the curve of the mushroom tip. Ash was enjoying herself. Ann looked very concerned.

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