Andi's Summer - Day 06 Pt. 01

Story Info
Friday Morning - Trained to be an entertaining entertainer.
9k words
4.33
13.6k
5
0

Part 7 of the 10 part series

Updated 09/22/2022
Created 12/27/2014
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Gilead39
Gilead39
21 Followers

Even though I was wilted and in a zombie state I was at Mr. Jacoby's door promptly at 8 a.m. Not wearing underwear beneath my light yellow summer dress made me feel sexy, yet wholesome. I needed to feel sexy just to return to his house.

On the way I held my head up high, chest out. I had value. I was an experienced cock-sucker. Surely he would let me suck his cock at least once today, maybe all day long if I was lucky. I made a mental note to not mention Mr. Cooper or his gifts to Mr. Jacoby.

I rang the bell. Mr. Jacoby's voice came through a callbox telling me to come upstairs as a buzzer opened the door. I found him naked in his bedroom fresh from a shower his hair uncombed and damp. He was standing facing the door with his fist on his hips. He looked like an altered image of Superman; his cock beckoned me, my mouth and my skills.

I scurried over to him and dropped to my knees. I handed him the pink envelope with my written homework. Finally, as he promised, I was going to have a taste of him. As I reached out he swatted my hands away and stepped back.

"Not so fast Andi, I need to walk you through your morning warm-up first."

Morning warm-up?

"Take off your dress."

I flushed in embarrassment; I glared at him realizing he had intentionally stood like that expecting me to rush to him and voluntarily commit myself to the oral act he knew I desperately wanted - needed. He caused me to humiliate myself. I was so angry that I considered biting his masculine appendage off first chance I had.

I slipped my dress up over my head as he told me that I was to use the top left drawer in the double bureau for my clothing. He made no comment regarding my instant nudity. I walked over to the bureau, opened the drawer and found my neatly folded school uniform stored there. The ties on the blouse should have been wrinkled; instead they were pressed flat. I folded my dress and placed it and my sandals carefully in the drawer and closed it.

As I faced him without a "hello", "how are you", or a comment on my dress he pointed to a white dress box on the unmade bed that was centered inside a multi-colored hula hoop. He must have recently placed it there and told me it was my uniform and that I could try it on for him after my exercises. He sat down in his chair and began to fondle himself.

"You know how to hula hoop, don't you?"

"Yes." I tempered a growl.

"Good, give me a good show and smile Andi; we are going to have another fun day."

This man; this aggravating smart-ass knew how to push my buttons. The last thing I wanted to do was to look happy and shake my ass for him, but I had no choice. I picked up the hoop, stepped into it and with my back to him spun the ring around me and let my hips take over. It was second nature; I had spent hundreds of hours twirling my own hoop thinking that it would keep my waist small and sturdy.

"Turn around and face me. Big smile!"

I forced myself to do his bidding using my pride of skill to make me seem pleased to entertain him.

I moved my hands and feet to strike the posturing of a belly dancer which gave my performance an Asian flair. He let me go through my entire routine twice before stopping me.

He failed to compliment me on my talent or dexterity.

"Do some jumping jacks for me."

Mr. Jacoby was just like any other dirty old man; he wanted to see my titties (his tits) flop around. He was in for a surprise because they were still tight and rose and fell in tandem. Of course I knew I would be spreading and closing my virgin girlhood for him to ogle. He let me do about ten repetitions before stopping me.

"I want you to modify how you do those, flatten your hands and cover your cunt with them on the down swing and look coyly into my eyes. Do five repetitions facing me and then turn clockwise and do three while looking at me, turn away from me and do five more and then turn again for three more and look at me as if you are pleading to be fucked. Those detailed instructions made me take notice. Did he have a reason for me doing jumping jacks?

I began the exercise questioning what he had in mind. I flubbed up when facing away from him and did seven reps. When I finished I was flush. Not from exertion but because I had enjoyed being so exposed and was thrilled to be watched as intently as Mr. Jacoby had scrutinized me with his eagle eyes. Turning a man on by just doing jumping jacks was a new notion.

"Change the five reps to seven and the three to five. Keep mindful of your hands when they are in front of your cunt. You are to look like a shy but horny virgin. Don't stop until I tell you to."

I was right he had a plan of some sort that he wasn't sharing with me.

Starting the exercise again I came up with some modifications that I thought he would appreciate. On the first profile I double-clapped my hands on the first repletion and on at the end of the last one. I did the same thing during the left profile. Instead of continuing to turn counter-clockwise when I finished the returning face view I reversed my turn. On the next frontal exposure I curled my forefinger on my right hand and let my left appear to grasp my wrist; it was subtle, but for the briefest moment it looked like I was fingering myself every other time my hands were downward. I added a hint of a shimmy when my butt was facing Mr. Jacoby. I hoped he liked my embellishments. He let - or made me continue on and on as if he was impressed or aggravated. I was perspiring profusely and my legs were shaking when he call out for me to stop.

"Very nice Andi, I liked your added flourishes." He had finally complimented me. "You and I are going to make a great team. Not that I will accept all your changes in the future; but within reason feel free to improvise."

I was grateful for...

Mr. Jacoby rode roughshod over my thoughts demanding my attention.

"Now I want you to face me and do some deep knee bends; keep your back straight, drop your ass right down to the carpet, fondle your tits and pinch your nipples as you do so. Ten repetitions to start."

Easy for him to say. I felt fortunate to be barefoot.

After completing the bends which compelled opening my knees a little he finally commented on my dildo pleasured swollen lips.

"I see you were priming your cunt earlier this morning. It looks like you are fully prepared to be fucked."

"Yes sir, I just couldn't keep my fingers away from me after all the marvelous things you did to me Wednesday. I finger-fucked myself Wednesday night, all day yesterday and this morning." The unprepared lie rolled off my tongue in my shy little girl voice as if rehearsed.

"Good, very good. I would like you to keep your cunt in that condition at all times." Without knowing it, Mr. Jacoby was giving me permission to use Mr. Cooper's Bad Boy every chance I had.

"I want you to slow down your knee bends and slowly open your thighs wider as you descend, and then thrust your cunt out toward me for three repetitions before returning slowly to your standing position. We'll add music later to make your exercises easier. Ten repetitions - take your time."

The knee bends were easy enough but the thrusts threw me off balance on the first, second, fifth and eighth reps.

"How can you make that work better, Andi?"

Embarrassed by my failures I rummaged my mind for a solution.

"Well sir, I think if were wearing my platform sandals the bends would look better. If I could lean back on my hands after squatting I think my thrusts would be more to your liking."

"Let's try that."

In my sandals the bends went smoothly and looked better because my ass dropped further below my heels. Resting on my palms the thrusts were much easier although I had to add a dramatic swirling spiral with each of my arms to return to the squat. Mr. Jacoby stopped me after the third rep.

"Let's see twenty repetitions of the thrusts alone."

As I complied I watched his expression change from judgmental interest to undeniable lust and fascination. I could imagine how my cunny was yawning and recoiling; pleading to be fucked. I was well aware that my modified thrust looked like I was humping an invisible cock hard at work between my thighs. My own imprudent thoughts started a moisturizing of my love canal.

I expected him to ravish me when I finished my performance.

"Let's put that all together. Facing me do five repetitions of each of the exercises in order. Do your hoop thing without the hoop, the jumping jacks and the squats without the thrusts."

I did the shortened version for him.

"Again. Ten repetitions this time."

I watched to see his impression; he didn't look pleased.

"No, that's not going to work. The jacks disrupt the flow of your dance and the squats. Let's try one more version and if it works that will be the end of your daily exercises for today."

Daily exercises - well every other day - could get boring real quick.

"Do a complete clockwise and counterclockwise routine of the dance, then do the same for your squats without the thrusts, and then do your thrusts separately as one exercise. Five repetitions for each turn and return."

Mr. Jacoby was asking a lot. The routine he wanted would be exhaustive. Since it would be the last one today I vowed to do my best. I was crushed by his observation when I finished the sequence.

"Needs a lot of work but I think you have the basics down."

To catch my breath I had bent forward and braced my hands on my clammy knees.

"Stay like that and back over to me." He spread his legs so I could back right up to the edge of his chair.

"I want you to bend your knees and bounce up and down like you had something nice and hard sliding in and out of your cunt. Add that shimmy of your ass once in a while. Go ahead."

Mr. Jacoby place his hand palm up between my legs letting it just brush my puffy lips. I felt electrified when his fingertips touched my clitoris. This was an exercise I would volunteer for ten times a day! I bounced and bounced bracing my hands on my knees.

"Shimmy."

Swaying side to side I felt my button ripple across his extended fingers and began to juice.

"Bounce - bounce - bounce, shimmy, shimmy. Bounce - bounce - bounce, shimmy, shimmy."

Mr. Jacoby stopped directing me; he didn't have to, I knew what he wanted and to be honest I craved it to continue forever. I looked up at the slanted mirror opposite us. I could see both our faces. I was beaming like a beauty pageant contestant and Mr. Jacoby was looking at our reflection too as he sucked his thumb.

I felt his free hand caress my left cheek and his coated stump tap at my anus. I was satisfied to let him do that for a while but my growing lust wanted more. I wanted his fingers inside me. I wanted him to violate my ass. Just when his efforts were getting really, really good, he stopped and withdrew his awe-inspiring hands. I was so close - so close to exploding. He had to know that.

Frustrated and humiliated once again I staggered to my feet.

"For your homework tonight and tomorrow I want you to practice the hoop, knee bends, thrusts and bounce. I'm sure you can find something to ricochet against. We need to strengthen your legs. Check out your uniform."

The tormenting bastard pointed to the white box on the bed as if he hadn't abandoned me at the worst possible time.

I lifted the lid and saw a small cluster of items that were black satin bands with white lacey trim and a very small matching apron. I also saw a pair of black patent heels with three thin, tiny crisscross straps across the toes and instep that promised little in the way of support.

"Sir, where is the dress?" I gave him a cute pouty expression.

"There is a dress, but there is no need for one around the house or pool; I want to be able to see your tits, cunt and ass at all times. As I told you Wednesday your tits, ass, and cunt belong to me now."

I didn't need to be reminded. I cringed at his insensitive and vulgar expressions in reference to my body parts and his claim of ownership. I had little choice. I knew I would look cute in the skimpy outfit, but had reservations just the same.

At the bedside my hands were shaking in rage as I grabbed up the apron to give me some immediate modesty. The wide silky band had a large pre-made bow with very long tails and had bra hooks at one end that clipped on the top left side of the apron. I realized that front panel gave me no coverage at all; it only covered a third of the way across my center front, my thighs were completely visible and the heart shaped hemline fell short of my fluffy muff by at least two inches. The tails hung down to the back of my knees.

Glancing over at Mr. Jacoby still seated in a leather upholstered chair in the corner I saw he had his now large thick cock in his hand and was slowly stroking himself as he casually watched me.

I picked up the first piece; it was a choker with three little silver bells hanging on black strings meant to be worn to the front. They settled just above the crease of my cleavage. Next were two wrist bands that simulated cuffs on a long sleeve dress. Next were two matching garters.

I turned to him, "Are there stockings?"

"Are there stockings, MR. JACOBY?" he corrected.

"Yes sir. Are there stockings Mr. Jacoby?" I slid the garters in place and they did look nice.

"No, you would just tear holes in the knees and I would go broke replacing them. That seemed like a reasonable conclusion, since I expected to be on my knees earning "boner bonuses" frequently, however I didn't like his insinuation that the fault would be mine; after all he would be the beneficiary of my efforts.

There were three sets of white stretch bands of two rows of the white satin lace.

"Where do these go, sir?"

"One set on your upper arms, your wrists and one set on your ankles, of course."

Of course. He was treating me like an empty-headed bimbo. The first set created the impression of cap sleeves and the second set the semblance of wrist cuffs and the third of little girl socks. The black patent heels were going to be a challenge; I had tried on a pair of 3 inch pumps in a shoe store in Marion once and nearly fell on my face. These were at least two inches higher and would have me standing on tip toes.

I picked up the black plastic headband with its fan-shaped simulated white lace maid's cap. Using the bureau mirror that was angled down to reflect the bed placed it on my head adjusting it this way and that until I thought it looked cute. Checking myself out I had to admit I looked sexy.

I turned to Mr. Jacoby, "Taa Daa!"

"Put on the stilettos."

The only closure on the black patent slides was the crisscross straps across the toes, no side support, and no ankle strap. I struggled to work my toes and feet into each of them. Maybe they would stay on.

Carefully, on wobbly legs with my back to him I stood there with my bare butt on full display; I couldn't move. What was wrong with me? I had spent nearly the entire day on Wednesday naked in front of him.

The box was empty. I realized this was to be my total wardrobe.

"Sir? I... I... I'm all but naked!"

"Exactly." His chuckle sent shivers up and down my spine. Was his intent to humiliate me constantly? Without any cover or support my breasts would jiggle and wiggle all over the place. Fortunately they were still young and firm enough to move in tandem. I had never been able to tame the roll, tumble and bounce of my big butt. My muff would be on constant full display; my lips would grow puffy and wet disclosing the state of my arousal. I hated the idea - I loved the idea!

"Come here."

I turned to face him knowing I was blushing. The flash startled me. His face was hidden behind a Canon camera.

Flustered, I whined, "You didn't say anything about taking pictures, Mr. Jacoby."

"No, I didn't. Do you think I need your permission?"

He had me there; he was the boss. "No sir, you just surprised me."

"Take one step toward me." The sound of my sole slapping the shoe seemed to be calling out for attention. His padded carpet had been a comfort on my bare feet; on these pencil thin heels it created a persistent threat of an awkward and embarrassing fall.

I wobbled a half-step and the flash went off again. He ordered me to smile stating that I had dimples; I should use them. Smiling wasn't a normal expression for me; at least not constantly.

"Another step."

He waited until I completed a step and told me to cup my tits before he took another shot.

"Another, bend your knees a little, and SMILE damn it."

"I can't; I have never worn heels this high, sir."

"Try harder. Keep your chin up, shoulders back and concentrate. By the end of the day you'll be a pro!"

Easy for him to say. I made a valiant effort and semi pulled it off. I was close to his chair.

"Stand in front of me. Use both hands and spread that sweet cunt of yours wide open for me."

"Sir", I whined.

"Do it!"

He took three shots straight at my pelvis as I trembled in front of him. At least my face wasn't being shown as he told me to use one finger of each hand to open my cunt, then two and then three. I wondered what those photos would look like.

"Stay." He raised the camera up to my breasts and face, told me to lick my lips and took three more shots telling me to lift my face, tilt it to the left and tilt it to the right. He turned on the video camera that was conveniently aimed right at the edge of the bed. Would Mr. Jacoby always be one step ahead of me?

"Sit on the edge of the bed, prop some pillows behind you and show me how you finger-fuck yourself."

Did he have to be so crude? When I was in place with my legs spread widely facing him I needed to be sure.

"You... you want me to masturbate for you?"

"Exactly. Imagine that my buddies and I are sitting here enjoying a beer and you are flirting with us as you diddle yourself. Make it an invitation for each of us to come over there and lick your cunt. Wait!"

Mr. Jacoby stood, walked over, stepped between my legs and showed me two spring loaded file folder clamps.

"These will enhance your experience."

The initial shock wasn't very thrilling at all as he applied first one and then the other to my unprotected nipples. They were tight and bit in well beyond snug.

He returned to his chair as I squirmed feeling the heat from my nipples spread across my chest.

I knew exactly what Mr. Jacoby would be viewing as I had practice my self-pleasuring skills in front of my mirror with my back propped up by the foot of my bed so I could study myself. I had perfected the initial teases, the subtle stimulations and the repeated deliberate orgasms (usually three), and the nearly violent and ferocious finale. My rehearsed routine was time consuming, but so very, very rewarding.

If I needed to rip one off I would lie spread-eagle on my bed and get it done; usually with the help of an underlined passage or tabbed page from one of Mr. Gilmore's discarded novels. Sometimes, when I was alone in the house I would sneak downstairs naked and straddle the arm of Daddy's leather chair and ride it like a pony until I came. It felt so daring to be naked downstairs.

Mr. Jacoby was about to learn that I wasn't a completely naive virgin that he was teaching to improve her cock-sucking skills; instead he would see that I had developed a sophisticated habit to pleasure my own genitals.

I always started with lightly touching myself all over; just brushing the surface of my flesh so the tiny hairs would straighten out and stand up. My hands were not my own; they were the hands of an ardent lover and explored every inch of my body. It was during this time I would choose what or who I would fantasize about. Mr. Jacoby had provided a fictional group of men for me to visualize.

That thought alone had awakened my love tunnel. I choose to imagine four men, similar in stature to Mr. Jacoby standing in twos on each side of his chair fully naked and stroking their cocks just for me. Each cock was different in length and girth; each looked delicious.

Gilead39
Gilead39
21 Followers