Two Friends in Need Ch. 02

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Rebecca requests to serve Sir again.
11.6k words
4.73
141.4k
27

Part 2 of the 9 part series

Updated 06/09/2023
Created 09/12/2003
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Before you read this story, may I suggest you go back and read Chapter 1 first, as it will help you understand the story line. When you read this story you will notice that outside of the sex of the characters that I avoid describing the physical appearance of the characters. This is done to make it easier for you the reader to place yourself into the role of the characters.

* * * * *

I received Rebecca's email first thing in the morning and as I sat there staring at her words I felt a familiar stirring in my crotch as my mind went over the possibilities for the weekend. I resisted the urge to respond to Rebecca's email, wanting to give careful thought to my response. I closed the email and attacked the pile of work sitting on my desk. The morning flew by, and by lunchtime I had put a large dent in my work.

During lunch I wrote my response to Rebecca's email.

Rebecca,

It pleases me to hear of your desire to serve me once again. I am honored with the gift that you present to me. Our last meeting was very much a pleasure. It has been a long time since I have played the game with someone who truly wants to submit, and to give up her control.

I will be at your place at 5:00 on Friday, your door is to be unlocked. You will not be returning home until Sunday. Have your overnight bag packed for Sunday.

I expect to find your new outfits and lingerie laid out for my inspection.

You are to be fresh from the shower; all traces of make-up scrubbed away.

Your hair is to be dried and brushed out.

When I arrive I expect you to be completely naked, kneeling in position the center of your living room, facing the door.

-Sir

After sending the email I called the boutique and talked to the manager. I explain that I wanted to bring Rebecca in to be fitted for a corset.

"The same Rebecca you sent in for the fitting on the black skirt and Blue silk top," ask the manager.

"Yes, it is the same Rebecca"

"I wanted to thank you for referring her to us, she called the next week and setup an appointment to come in and get some new outfits," the manager explained.

"So were you able to help her out?" I asked. I was curious to know what the outfits looked like, but did not want to come right out and ask.

"Oh yes we were able to help her, in fact we just finished up the alterations she requested and delivered them this past Saturday."

"So you will be able to help us with a corset?" I asked.

"I will make sure that I have several to pick from," the manager assured me.

We setup an appointment, Saturday morning, for Rebecca's special fitting.

After talking to the manager, I thought about what she had said about the alterations. She said "alterations she requested", that piqued my interest, not necessary alteration but ones Rebecca requested.

With that done all that was left was a trip to a special adult toy store and wait for Friday. The week crawled as my thoughts continued to return to the upcoming weekend with Rebecca. Between going over the events that had transpired since that first email that I had dared to send, and me wondering just how far I could push Rebecca, and just how fast she wanted to be pushed, my thoughts were occupied by little else. So far things could not have gone better, almost too good. It would make the weekend even more of a challenge for me.

Friday finally came and I headed to Rebecca's, I arrived a few minutes early, trying to catch Rebecca off guard. As I reached for the doorknob I thought I caught glimpse of a shadow move in the sidelight of the door. When I opened the door there was Rebecca obediently kneeling totally naked. I closed the door and locked it then walked over to Rebecca circling her, inspecting her like a possession.

I did not speak a word just enjoyed Rebecca's embarrassment as I continued my inspection. The blush that covered her skin just made her look that much more vulnerable. As hard as it was for Rebecca to kneel there naked awaiting my next instruction, her hard nipples and her shallow breathing told me she was getting turned on. I reached out and stroked her hair, then bent down and kissed her on the forehead and whispered just one word, "stay". This caused Rebecca to let out a slight whimper as I straighten up and walked toward her bedroom.

As I enter Rebecca's bedroom lying on the bed was four sets of lingerie. The first set was red satin, the second one was white lace, and both consisted of a thong, matching garter, and a very sheer bra. The third one was transparent black satin, the forth one was a pale pink lace and both consisted of a thong, matching garter, and a pushup bra with half cups. Next to the lingerie where several pair of stockings and next to the stockings were the black pumps from our last meeting along with a pair of white open-toed with four inch heals, and red pumps with five inch heals.

Hanging on the closet door were three outfits. The first outfit was a white linen sleeveless dress that buttoned down the front. As I looked at it I could see that the top two buttons had been removed, and to my surprise the very bottom one had also been removed. The second outfit was a sheer pink sweater with a dark blue plaid pleated skirt; the outfit almost had that schoolgirl innocence. The third outfit was a red satin dress, with a scoop neck and a four-inch slit up the right side.

By the time I was done inspecting her purchases my mind was reeling, Rebecca was in her living room naked and kneeling in position, a perfect picture of submission. Her purchases reinforced that submission, and now she was waiting for me to use her for the weekend. I headed for the living room and Rebecca.

As I returned to the living room Rebecca was still kneeling obediently. I walked over and stood directly in front of her, to her credit she resisted the urge to raise her eyes to look up at me. The effect of me standing over Rebecca was amazing, her breathing became shallow and her skin blushed a pale pink. As I looked down at her, I spoke, "Rebecca, take my cock out."

Rebecca raised her hands and eyes to my crotch. Her fingers struggled with the zipper as she was trembling. She finally got the zipper down and reach to pull my cock out which took some doing as the situation had me semi hard. Once she had my cock out it quickly went from semi hard to fully erect pointing directly at her lovely face. As my cock hardened in Rebecca's hands she swallowed and let out a sigh.

"Clasp your hands behind your back, Rebecca", I spoke in a quiet but firm voice. Rebecca slowly let my cock go and moved her hands behind her back. "Now kiss my cock." Rebecca leaned forward and took the tip of my cock between her lips and swirled her tongue over it. A sigh escaped Rebecca, as the kiss ended and her lips lost contact with my cock. Between the warmth of Rebecca's lips and tongue and the sudden coolness of the moisture her tongue left behind caused my cock to twitch. "Now suck my cock, Rebecca. Show me how much you want to please me." She leaned forward again and took my cock between her lips and started to run her tongue over the head again.

She then started to take more of my cock in running her tongue over the shaft as she did. I knew I would not last very long as she continued her oral servicing. She soon had my cock buried in her throat and still I could feel her tongue running over the base of my cock. She continued with her tongue as she started sliding her lips slowly up my shaft then back down to the base sliding the head of my cock into her throat. When my cock would be buried in her throat she would swallow causing her throat muscles to tighten on my cock head.

Her pace quickened and she was soon fucking her throat with my cock. I could feel my knees getting week and that familiar tickle in my balls, I knew I was close. I reached down and put my hands on the back of Rebecca's head and took over the fucking of her throat. Rebecca fought to keep up with me gasping at a breath of air when she could. One last time I pushed my cock into her throat only this time I let out a loud growl stiffened and released my cum straight into her belly. It was all I could do to keep from collapsing as my climax took over. I released my grip on Rebecca's head allowing her to slide my cock out of her throat letting her breath again. As I stood there on shaky knees I heard Rebecca sucking air in through her nose as she still had her lips sealed around the head of my cock. After a few minutes Rebecca's breathing became more regular and I felt her swallow and then start to gently suck on the head of my cock draining every last drop of my cum. When she was finally satisfied that my cock was drained and clean she released it from her lips and knelt straight up in position.

I spoke; "Rebecca." She hesitated at first then slowly raised her eyes to mine. Her eyes sparkled as they met mine, I could not help but smile. "Put my cock back." Rebecca reached up and took my soft cock and carefully tucked it back into my pants and pulled the zipper back up. After she was done she moved her hands back behind her.

I sat in one of the living room chairs and took in Rebecca's submissive beauty. After a few minutes, I spoke, "Rebecca, go and wash your face and then put your makeup on, remember I want it on the sluttish side. Do not brush your teeth or rinse your mouth out. Then put on the black lingerie and black heals and come back and stand in position. You have thirty minutes, now go."

"Yes Sir," was Rebecca's only words as she got up and headed for the bathroom.

While Rebecca was busy I sat there patiently waiting. It was not long and I heard the bathroom door open and then Rebecca's soft footsteps as she headed for the bedroom. I sat there daydreaming about how lucky I was to discover this side of my friend, and then to get the opportunity to fulfill her needs. Rebecca did not seem as nervous this time as she was the first time, but I had a feeling that would change a bit as the weekend progressed. I was going to do my best to push her limits even further this time. My gut feeling was that if I did not push her she would have been disappointed.

My thoughts were broken by the clicking of Rebecca's heals on the hardwood floors. She enter the living room and proceeded to the center turned and faced me, spread her feet just wider than shoulder width, back straight, hands clasp behind her neck. I stood up walked over to her and took her by the chin and lifted her face so I could look her in the eye. Her eyes sparkled and her smile lit up her entire face. I moved my hand from her chin and took a step back and then proceeded to circle her, subjecting her to glaring scrutiny. Again gone was the conservative confident executive, replaced by a submissive sexy slut. Her lips and nails were blood red, her eyes bold. As I continued my inspection it was obvious that Rebecca was very much into the game. Her aureoles were swollen and puffy, and her nipples were sticking straight out.

I came up behind Rebecca and reached out and lightly ran my fingers from just below her armpits down across the sides of her satin encased breasts. Rebecca took in a quick breath and held it as my fingers made contact with her sensitive skin. As my fingers traveled down to her breast she started to breath again but her breathing was a little faster and a little shallower. I stepped closer to her and continued to let my hand lightly trace over the satin cups of her bra slowly circling her breast spiraling toward her nipples. As I got to her aureoles I limited my touch to one finger. With the same light touch I started to trace circles around her nipples, being careful not to touch her nipple. I then leaned forward and brought my lips very close to her neck just below her ear. I did not say a word; just let her feel my breath on her neck. This coupled with my continued tracing of her aureoles caused her breathing to be come more ragged and her nipples to stick out even further.

I then moved my hand to the under side of her breast and started, ever so lightly to caress them. As I did this I brought my lips closer to Rebecca's ear and in more of a hushed voice than a whisper, "I see you are enjoying being my little slut."

I pulled my self closer pressing my growing cock against her. Slowly I started sliding my right hand down, over her stomach, to her pussy, while continuing to caress her breast with my left hand. As this was going on I continued, "I am going to treat you like the slut you want to be. I am going to display your charms for others to admire. If you are obedient you will be rewarded with extreme pleasure, if you are disobedient then you will be punished."

Rebecca was almost panting now and her body was trembling. I ran my hand over the tiny piece of satin that barely covered her pussy lips. The satin was soaked with Rebecca's juice. "Rebecca you are such a slut, your pussy is completely soaked and I have not even touched it yet. I am going to so enjoy using you this weekend. One last thing for you to think about Rebecca, I intend on introducing you to the pleasure of pain."

With the last statement took her right nipple between my thumb and forefinger and squeezed it hard. I continued to increase the pressure until Rebecca let out a gasp. As I released her nipple I felt a shudder run through Rebecca's entire body and a gush of juice from her pussy onto my right hand.

"You Little Slut! You just made a mess of your panties" I half scolded, half teased Rebecca. "Now take them off, go rinse them out and hang them up to dry, you will have to go without them now."

Rebecca let out a gasp and went bright red with embarrassment. She then peeled her soaked panties off and then stood back in position with her panties crumpled in her hands. In almost a whisper Rebecca spoke, "May I please be excused to rinse my panties Sir."

I did not answer her at first; I wanted her to wonder what she should do. I could see the indecision in her face as she wondered if she was to go or if she had to wait for the permission she ask for. After a few moments I finally answered her, "Yes you may be excused, and once you are done rinsing your panties out you are to put on the white outfit and pack the rest of your outfits in your garment bag. Once you are dressed and packed, place the garment bag with your over night bag by the door then come back here. You have ten minutes, now get moving"

"Yes Sir", was her only words as she turned and walked to the bathroom. A few minutes later I heard Rebecca's hurried footsteps on her way to the bedroom. I knew ten minutes would be pushing it and doubted that she would make it on time. I figured she would be close but would never make it, which would give me a reason to warm her ass before we left.

At ten minutes she was hurrying to place her luggage by the door. She then moved to stand in front of me. The dress came to mid thigh, which would have been a bit long if not for the missing button at the bottom. With the last button missing the dress had in effect a slit right up the front to just three inches below her crotch. Then to make it even better with the missing buttons on top the dress was opened to just above the clasp of her bra. The black lingerie was quite noticeable under the white linen. This emphasized the fact that she did not have on panties.

I stood and circled her in silence, again inspecting her like a piece of property. As my inspection continued her breathing quickened and she began to tremble ever so slightly.

I brought my lips very close to her ear and whispered, "You were late"

"I'm Sorry" Rebecca tried to apologize but I cut her off.

I then moved Rebecca closer to the front of the chair. Placing my hand on her back between her shoulders I applied gentle pressure causing her to bend over. I continued until she was bent over completely holding on to the front of the chair for support. With her bent over I pulled the back of her dress up over her naked ass. Between being bent over and her heals the muscles in her thighs and ass were pulled tight. I could not resist running my hands over her ass. She let out a low moan as she felt my caress. Then slipped a finger between her thighs and down her pussy slit finding her almost dripping wet. This contact caused her legs to shake and her breathing to quicken.

"Rebecca, so are you ready to be my little slut? Are you ready to be used by me for my pleasure? Are you ready to be obedient? And are you ready to accept your punishment when you fail to please me?"

As Rebecca listened to my questions her breath became ragged and shallow, her trembling became more pronounced. She took a deep breath trying to gain compose enough to answer. Then her answer came almost in a whisper, "Yes Sir"

"Louder, I need to hear you clearly!"

Rebecca was all but panting fighting to compose herself, which was made that much more difficult given her present position, and then with great effort she blurted out, "OH GOD! Yes Sir! I Am Ready To Be Your Little Slut. Use Me For Your Pleasure! I Will Obey You, and Accept Your Punishment When I Displease You!"

Just as she got her response out I gave her four quick swats, leaving my handprints on her ass. The swats got her so off guard that her mouth opened to let out a scream but nothing came out. And before she could totally recover from the swats I had her standing back in position. Her face was a mix of confused emotions but her eyes were wide open and sparkled with pure lust.

Again I moved behind her and moved my mouth close to her ear and Whispered, "You have done well, you will be rewarded later, but for now it is time to go."

I then picked up her garment bag and overnight bag and headed for my car. Rebecca picked up her purse and locked up and hurried to catch up with me. As I was placing her bags into the trunk she caught up. I opened Rebecca's door for her. As she got in her outfit afforded me a great view of her naked pussy. Then to my pleasure she hiked the back of her dress so her naked ass was on the seat.

As I got in the drivers seat I looked across at Rebecca, a woman I know to be strong, confident, independent, sitting there waiting to serve me, to be used for my pleasure. Pulling away I smile knowing this is going to be a very memorable weekend.

While driving I see that Rebecca has relaxed a bit so I decide to push her a bit. "Rebecca, unbutton your dress," came my simple command.

Rebecca's breathing picked up as soon as she heard my command. I watched as her fingers were shaking as she reached for the first button. Three buttons later, her dress was unbuttoned. With her dress opened she was on display for anybody driving past. Being exposed as she was brought back a bright red blush to her face and across her chest.

"Now Masturbate Rebecca, but don't cum."

Rebecca's blush deepened, as her hand slowly moved toward her naked pussy. She sucked in a deep breath as her fingers came in contact with her pussy lips. Soon she was moaning and arching her hips against her hand as she continued. Her head was thrown back her eyes closed tightly she was lost in the pleasure she was giving herself.
It was all I could do to concentrate on driving; her actions, her exposure, the sound of her labored breathing and the sweet aroma of her sex had my cock rock hard and my mind swimming in the possibilities that awaited this submissive slut.

I pulled into an alley about a block from the restaurant. I turned and looked over at Rebecca who was lost in her pleasure, smiled and whispered her name, "Rebecca." She did not respond still lost. I again called her name just a bit louder, "Rebecca" Again, she did not respond. So then I called her one more time only this time a bit louder than normal "Rebecca!"

Immediately her eyes snapped open and her head turned. As soon as she made eye contact with me she quickly looked down. But her hand never stopped and I could tell she was very close to her orgasm, right where I needed her to be. "Rebecca, Stop!"