Annie Babysits the Kids Ch. 03a

Story Info
Fiancé further humiliated as a dress-up doll.
5.9k words
4.42
152.3k
65

Part 3 of the 9 part series

Updated 10/31/2022
Created 07/22/2007
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
DocCIS
DocCIS
1,543 Followers

Chapter 3...A Day at the Mall

In Part One I told of watching my girlfriend Anne-Marie blackmailed into having sex by the guys she used to babysit and how aroused and responsive she was--and how unbelievably excited it made me. Part Two described how she further became enthralled in their clutches.

The adventure continues...

*********************

Part 3A - Annie gets prepared...

I called Annie the day after her second ravaging and subjugation by William and Brian to ask how her babysitting went. She stuttered a few moments before replying it went fine. Asking if anything was wrong she explained she was tired because Mr. and Mrs. Strauss did not get home until late and needed some rest.

I knew they were barely gone an hour before their evening was unexpectedly cancelled and Annie had returned home early after being thoroughly used by both guys; however, I didn't press the issue. Telling her to take it easy and knowing how flustered she was from the night before, I told her I'd see her later in the day.

She seemed herself again when I went over to her house in the afternoon. I was disappointed seeing her dressed conservatively in jeans and a sweater--of course, with her parents around I wouldn't have expected her to dress provocatively. Still, remembering the night before I was curious and even anxious to see if she would follow Brian and William's "Rules."

We sat down to watch a movie; however, she seemed constantly distracted, often staring ahead not paying any attention to the movie. Asking if anything was wrong, she explained she was still tired from babysitting and for me not to worry about it. I knew exactly what she was thinking about, but could not tell if she was trying to figure out how to get out of it, or reminiscing on how she enjoyed the night's events.

The ringing of the telephone startled us, breaking both our thoughts...

"Hello?" she answered.

I saw her tense up as she glanced over to me, so I pretended not to notice as she kept looking over to me while on the phone. She stammered something about it being one of her friends from college who was upset about something and asked if I would mind hanging up the telephone when she went up to her room to talk in private. I agreed and she quickly ran up stairs.

"OK I'm on, you can hang up!" she yelled down to me.

Knowing something was obviously up, I hung up the receiver, but curiosity getting the best of me, slowly lifted it again to my ear.

"Who else is there?" I recognized Brian's voice over the telephone.

"Bob, my fiancé," she answered.

"Now Annie, you weren't thinking about breaking our rules, were you? Remember, you are not to have sex without our approval."

"I remember, and no, I haven't had sex with him." she answered vehemently.

"You haven't had sex with him WHAT slave?" Brian's tone asked coldly.

"I haven't had sex with him Master" I heard Annie mutter.

"Good" he chuckled. "Now, I want you to come and pick Billy and me up. We are going shopping at the mall."

"What?" I heard Annie protest. "I can't just leave. What will I tell Bob?"

"I don't care what the fuck you tell him. Just be here in half an hour, understood bitch? Or would you rather have him get one of your lovely videos to watch?"

"No, I will come as soon as I can," I heard Annie whisper.

"I'm sure you will CUM," I heard Brian laugh with his play on words.

Hearing Annie hang up the phone, I quickly hung up my receiver and sat back down on the couch. Annie came down the stairs looking nervous. Asking her if something was the matter, she told me Sally, a friend from college, was upset at breaking up with her boyfriend and needed to go over and comfort her.

I knew Sally's father, and he had recently dropped off her car for some work at the auto shop where I worked. He had told us Sally would be gone on a foreign exchange trip to Europe the entire summer break, so I knew Sally was thousands of miles away!

Telling Annie it was all right I asked if she wanted me to drive her over.

"No!" she yelled with her eyes wide.

Again I asked if something was wrong and she quickly regained her composure telling me no, she didn't know when she'd be home so would drive herself.

I said it was alright and told her to call me later.

*********************

I should take some time to describe my feelings. Don't get me wrong, I love Annie and know Annie loves me...that is not an issue, and one I feel never will be an issue. The fact we are engaged is testament to our love.

No, love has nothing to do with it...this was pure sex. I have always loved the exhibitionist side of her...it was not only pride but a turn-on seeing other men lusting after my girlfriend in high school. The knowledge I was the only one who could win her heart has been something meaning a lot to me, regardless of the pure physical attraction most men feel towards her.

Annie and I have always had a good and active sex life, her more than I. She can orgasm numerous times, each one more powerful than the last to the point where I've literally been too exhausted to continue, or she herself has almost past out. She has a remarkable sex drive and although at first it sounds like it would be the best thing in the world to have a girl like that, in some ways you start to feel you cannot keep up with her.

We've discussed threesomes in the past and although the discussions turned us both on, we never could figure out how to get involved in something like that. The thoughts of seeing Annie with another man may have caused jealousy or even anger with some men, but for me it oddly brought a sense of pride and excitement.

Again, I know our love between us is something we both cherish, but the pure physical act of sex is not part of that. We've made love many times, but when we have pure sex, it is something I found I cannot keep up with her. Now that she had somebody on the side to help and I could watch has been an incredible turn-on to me and something I was curious to see continue!

*********************

I left her house and immediately drove to the Strauss' end of the neighborhood, parking my car and waiting down the road. I was still in sight of the house, but Annie would not see me coming from the other end of the neighborhood. I was anxious to see what the boys had planned next for my gorgeous slave-fiancée...

About 20 minutes later Annie's car drove up to the house and pulled into the Strauss' driveway. When she got out of the car I immediately noticed she still had on her jeans and sweater. Slamming the car door I could tell she was angry as she stomped up to the door and rang the doorbell. Brian answered and I saw them talking, and then yelling, when suddenly Brian slapped Annie across the face!

She stood there holding her hand to her cheek in surprise as Brian yelled something at her. I was too far away to hear what they were saying, but saw Annie's head bow down as she stood there.

As I sat wondering what they were saying I realized how lucky I had been previously, being able to not only watch Annie's exploits without detection, but also being close enough to hear. I would never be able to continue following her without discovery and needed to think of an alternative. There was nobody else I could get to follow her as I did not want anybody else to know about this, though had a few friends who would jump at the chance! Many of my friends had been after Annie throughout high school...she was the hottest girl around and all had tried one time or another to get into her pants, especially my best friend Rick.

My mind wandered thinking up elaborate schemes of bugging her, hiring a private investigator, and so forth—all far to elaborate and embarrassing as I would have to admit I was more interested in knowing what she was doing, not upset at her cheating.

Finally, it hit me--her diary! Annie has kept a diary since she was 12-years-old. One night while drinking she confided to me how she recorded EVERYTHING--good or bad--in her diary. Her parents once discovered it and had grounded her finding out about her playing hooky from school, so she cleverly kept two diaries: one "hidden" in her night stand being a "Rated-PG version" as she called it in case her parents ever read it again; another was her "Rated-X version" where she wrote everything ever happening to her, including sex with me. This way if her parents tried to find out what she was doing, they would not look further than the "decoy" diary. Although it took a while to maintain the duplicity, it had served her well as her parents thought she was the model daughter. At the time she was now on the fifth volume, even telling me where she kept them hidden in her closet.

Although I would have to stay far enough away to watch Annie undetected, I realized I could fill in the gaps through her diary.

I have since read many pages of Annie's diary and can describe much of what has happened to her in these events--even what she was feeling at the time. She is brutally honest in her diary and I can now tell her story in full:

**********

The argument at the door was due to Annie's attire. Brian was scolding her for not dressing as she was told.

"Fuck you Brian. I'm tired of your petty little games. I've followed through so far and you are lucky I even came over here, but I want out now!" Annie yelled.

Annie suddenly felt the hard slap of Brian's hand across her face.

Staring at him in shock Brian yelled at her "Do not EVER speak to me in those tones again bitch! I told you I would give those tapes to everybody you knew and I meant it! Do you want your father to see those tapes? How about your dweeky fiancé? Gee, what will your school say if those tapes ever became public? And what about your parents--ever think of what would happen to their bank loan if my parents found out about you fucking their kids while babysitting? Do you want that to happen bitch?"

The Strausses were managers of the local bank. Annie's parents had taken a sizeable loan from the bank to pay for their house and Annie's school, mainly approved through their friendship with the Strausses. I knew they were far behind on payments and it was only their friendship with the Strausses keeping the house from being foreclosed and worse happening to them, and apparently Brian knew that as well...

"No" Annie whispered dejectedly.

"No what?" Brian demanded.

"No Master," she muttered.

"Good, now I asked why you didn't dress up like you are supposed to" Brian asked icily.

"I told you my fiancé was over. I couldn't just walk out of the house dressed like a whore with him there." Annie whispered. Seeing the anger in Brian's face, she quickly added "It won't happen again, please...please don't show those tapes to anybody" she begged. "I'll keep clothes in the car I can change into when needed, but please don't show those tapes" she pleaded.

"Please what?" Brian asked, obviously enjoying her predicament.

Annie's head bowed further in total defeat, "Please Master."

"I will think of a suitable punishment, but first we must pick up Billy." he told her.

**********

They got in her car and started driving away, me following far enough behind so they would not see me. Even before reading the events in her diary, I knew Annie was probably too upset to pay attention to her surroundings and see me behind her; however, I did not want to take any chances.

William was waiting outside his house as Annie's car drove up, getting in the front seat. As they drove away, I again followed at a safe distance to avoid being seen.

As I was following I suddenly saw something fly out of the passenger's window. Driving by I recognized the sweater Annie had been wearing moments before!

Several miles further down the road I saw her car swerve and a few more moments something again flew out the window—this time the unmistakable outline of a bra. It seems the boys not liking her attire were having her strip in the car.

**********

"Excellent," William said with satisfaction as Annie sat behind the wheel naked from the waist up.

She had trouble getting her bra off while driving the car and sat there red with shame as the two boys ogled at her exposed breasts. William laughed and said he would help her as he turned on the car's air conditioner to maximum. Embarrassed and angry as the boys' leered at her, she continued driving fully aware of the cold wind on her breasts making her nipples stand out hard as rocks.

"Now your pants" William ordered.

"What?" Annie stuttered. "I'm driving!"

"I'll steer," Brian said from the middle of the seat, "You just follow orders. Got it slave?"

"Yes Master," Annie muttered.

With some difficulty, after taking off her shoes she pulled her jeans off.

"Everything!" William ordered looking down at her lap.

Dejectedly Annie slowly pulled off her underwear. Even with the air conditioning blowing on her, her body burned from embarrassment driving naked while the two boys stared at her. She hoped nobody could see her as she drove in this state of humility.

This time she only mildly protested as William grabbed her clothes and threw them out the window.

"But I don't have anything else to wear!" she explained.

Brian and William glared at her as she dejectedly stared ahead and drove.

"Get on the highway, we are going to the mall," Brian told her.

Annie drove on the highway, trying to sink into her seat so passing cars wouldn't see her state of undress.

She tried to blot the entire incident out of her mind when suddenly the sound of a semi-truck's horn broke her reverie. Looking up she saw an eighteen-wheeler had moved up beside her, the driver waving at her through her sunroof.

Mortified she tried to shut the sunroof, but Brian grabbed her hand saying, "No, I think we'll keep this open" he laughed.

Annie gasped and almost swerved off the road as Brian firmly squeezed her right nipple between his fingers, sending a shock throughout her body. In her embarrassment, the cold air blowing on her body, and the boys and other drivers on the highway seeing her naked, she felt her heart and breathing quicken realizing she was getting aroused! She tried to act nonchalant, staring straight ahead attempting to ignore the rush of blood through her body and the tingling wetness between her legs.

Annie clamped her hands around the steering wheel trying without success to ignore Brian as he massaged and squeezed her breasts, the truckers watching and beeping their horns from their high vantage point, and the reactions her body was having.

**********

For the next twenty minutes I watched as semi after semi pull up to Annie's car, beeping their horn before moving on to let the next truck pull alongside her car. I'm sure the news of a beautiful 22-year-old naked woman on the highway was traveling across the CB radios of every trucker like wildfire.

**********

Finally to Annie's relief they pulled off the exit to the mall. As they were driving up she looked at the boys. "You know I cannot go into the mall like this."

"Don't worry, we'll find something suitable for you to wear," Brian said as he leered at her. "Just park the car."

Annie pulled to the far end of the parking lot turning off the ignition. Brian asked her measurements and shoe size, writing them down as both he and William got out of the car.

Taking the keys out of her hand, Brian laughed at her, "Don't walk away we'll be back in a few."

**********

As they walked into the mall I saw Annie lay down in the seat obviously to conceal herself from anybody passing by.

About an hour later the boys returned carrying a couple bags and getting into the car...

**********

"Here slave" said Brian, "we brought you something to wear."

William snickered as he said "Unfortunately we didn't have enough money to buy any underwear, but you can go without for now" he laughed.

Though upset, Annie grabbed the bags thankful to have clothing once again. Suddenly her eyes opened wide as she looked into the bag, "I can't wear this!"

William reached over and grabbed Annie's long hair, "What did you say, bitch?"

Quickly Annie replied, "Nothing Master."

"Good," William smirked, "now get dressed so we can finish shopping."

Annie slowly pulled out her "clothing" the boys had bought. The first item was a leather bustier with metal rivets all over the seams, lacing up the front. Annie immediately thought of a biker chick she once saw as she held it up.

With the boys leering at her, she realized she should be thankful for anything--even so revealing--to cover her nakedness so quietly began to put it on.

As she laced up the front she discovered it was almost two sizes too small! "Masters," Annie mumbled weakly, "this is too small."

Brian told her, "We decided it was the perfect size. Though they did have the size you gave us this one will do just fine. Put it on!"

Without another word, Annie struggled and put the bustier on, having to loosen the front lacings several times causing the leather to show more and more of her torso. After it was tied up she had to play around tucking in her breasts to get it to look right, the boys ogling at her the whole time. By the time she was done, the lacings were spread apart by almost 5 inches showing much of her middle chest and cleavage, her breasts pushed up incredibly high.

"Very nice," William said admiringly, "now the rest."

Annie didn't want to know what else there was, her humility was so great, but reached into the bag and pulled out a leather miniskirt. The skirt zipped on both sides and looking at the tag she was thankful it was the right size; however, pulling it on she realized the skirt was so tiny it barely covered her bottom if she bent over.

"I can't wear this" she protested, knowing inwardly it was useless.

The boys smiled at her and said nothing. Adjusting the skirt as much as she could—she realized there was a fine line between her ass hanging out if it were too high and crack of her ass showing if it were too low. She finally found a middle ground where the skirt ended up being several inches below her hip bones barely above her trimmed pubic hair, but it would have to do; otherwise she would be walking around exposing her ass to everybody.

She reached into other bag, feeling a pair of shoes and pulling out a pair of four-inch black spiked heel shoes with silver studs all over them. Glaring at the smiling boys Annie slid them on her feet, noticing the straps around her ankles matching the rivets in the bustier. Surprisingly the shoes were very comfortable and of all her clothes, were a perfect fit.

"Good," Brian said. "Now, get out of the car and model for us."

**********

I saw Annie step out of the car and even from my distance couldn't believe how hot she looked. She was the most incredible picture of pure sexuality I had ever seen. Her long legs were accented by the high heels and the incredibly short skirt. And the way her breasts bulged out of the bustier made her chest look twice as large as normal. I silently admired the guys' taste in clothing!

**********

"Very nice," William said approvingly, "but we are missing something aren't we Brian?"

Brian grinned, "Right you are Billy my boy, she needs her jewelry!" He reached into his pockets and pulled out a black leather dog collar with spikes on it.

"Oh no" Annie said, "I am NOT wearing that!"

Brian smiled as he walked over. Before putting it on he showed her the tag: "Bitch in heat" and Annie felt her face flush with shame, standing there as he put the collar around her neck.

Annie could feel fire burning behind her eyes. At this point she was so pissed at these boys, part of her not knowing why she was letting them continue, another part knowing she had no choice. Her humility was complete as she grasped the realization she was totally subservient to them, powerless not do whatever they asked of her.

DocCIS
DocCIS
1,543 Followers
12