Two Friends in Need Ch. 09

Marie looked at Anna, who was beet red from listening to our discussion, "After getting to know Jordan a bit better this evening do you want him to fuck you?"

Anna's eyes looked at Marie then me, then she locked eyes on Rebecca, it was like they were sharing their thoughts without speaking. Anna turned and looked Marie right in the eye, "Ma'am I need to know that Rebecca is ok with me letting Jordan fuck me before I agree."

Marie smiled, "Anna that is so sweet of you to consider Rebecca's feelings in your decision. If Jordan is ok with it I think you should ask Rebecca for permission, and if she gives it, you should then ask her to tell Jordan it is ok"

Anna blushed again as she looked at Jordan, "May I ask Rebecca permission to fuck you, Sir?"

Jordan nodded and smiled. Anna turned to Rebecca, looked her in the eye "Rebecca I know that Jordan is not only your Master but a very dear friend and I do not want to cause issues between you and him, so I am asking for your permission to let Jordan fuck me." Anna continued "I will owe you so much if you let me have this experience."

Now it was Rebecca's turn, again it seemed that slut stepped back a little and Rebecca stepped forward a little, "Anna me and my Sir have discussed this possibility and even though there is going to be a part of me that will be a jealous and not happy about sharing my Sir's cock I know it is not my decision. I have to accept and trust him that I am his and although he is fucking you, you belong to Marie and she is in control of your actions. So for what it is worth you have my permission to fuck my Sir."

"Sir, please fuck Anna until she passes out from pleasure, I want her to know why I give myself to you so completely."

I just chuckled, "I will do my best slut"

Anna looked at Marie, "Ma'am may I take care of slut, she has not cum yet"

"Yes you may"

Anna leaned over and kissed Rebecca then basically attacked her pushing her onto her back and the proceeded to mimic slut's actions. By the time Anna got between her thighs Rebecca was squealing and panting. I looked over at Marie and nodded, she smiled and stood, walked over to where Rebecca was flailing as a result of Anna's work. She knelt with her knees on either side of Rebecca's head lowers her pussy onto her face. It was quite the sight Anna buried in her slit munching away while Marie was sitting on her face grinding her pussy into her face.

I gave them a few seconds to get in sync with each other then I knelt behind Anna and aimed my cock at her slit and pushed forward just enough to push the head into her slit. Anna let out a squeal then went back to work on slut. I slowly pumped my cock in to her, it was so hot and wet that even though she was tight I had no problem getting my cock buried in her. I just held it there while she continued to service slut, I knew it was effecting her because I could feel her contracting her muscles trying to get me to start fucking her.

I raised my hand and looked at Marie, she had a look of concern on her face but before she could react I landed a swat on Anna's ass, "I did not give you permission to fuck my cock now stop". Anna squealed and her pussy muscles froze. To her credit she never stopped munching on slut. I had cupped my hand so the slap was much louder than it stung.

Slut must be a natural and eating pussy, even with the distraction of Anna's attention she still had Marie cumming quickly. As her orgasm hit her she let out a low growl and sprayed cum all over slut's face which triggered her orgasm, screaming and pushing Anna's face tighter into her slit. Marie managed to stand and stagger over to the chair and collapse. Rebecca's grip on Anna head relaxed as she slowly recovered.

With my cock still buried in Anna's hot pussy, "Slut, relaxed position by my chair. You may enjoy you wine while I reward Anna for letting us push her limits and help you get back on your journey." Rebecca slowly slid from under Anna and moved to beside my chair and knelt in position.

I started to slide my cock in and out of Anna. I started with long slow strokes letting her get used to my cock. That only last a few minute as her tight pussy was begging to be pounded and I started picking up speed and soon was pounding into her pussy. Anna started matching my strokes pushing back against me panting "Yes oh my yes fuck me harder" I started pounding her with everything I had. Suddenly Anna let out a high pitched squeal and squirted cum all over me as her orgasm consumed her. Her pussy spasmed squeezing my cock and triggering my own orgasm. I howled as I slammed my cock home and just emptied my balls into her pussy, then I collapsed beside her.

It took a few minutes before I was recovered enough to get back in my chair. Anna took a little longer to recover but she also slowly got back into position. Both of our sluts looked well used but content.

"Slut, since you have had time to recover you need to get a round of refreshments. Marie, since it is close to the end of our play for this evening I propose a nightcap to celebrate this wonderful evening of journeys continuing and boundaries broadened?"

"I agree a glass of wine, red."

"Slut, wine for our guest, a beer for me no glass, and wine for you."

"Yes Sir." Rebecca stood and headed for the kitchen.

Anna was kneeling in position, she looked a tad worse for wear but had a look of contentment. "Anna moved over to Marie and kneel in position there."

"Yes Sir."

Anna moved to Marie and knelt in position. Marie reached out and stroked her hair, as she did this Anna leaned into her touch, content and happy.

A few minutes later slut came back carrying our drinks on a tray, she set it on the coffee table and served Marie first then me, then she served Anna and then she picked up her wine and came and knelt by me.

"Anna since you have been following my house rules since you arrived you now need to know that once we are done playing and just relaxing you can relax also. You need to still stay kneeling by Marie but you may sip your wine and relax."

"Marie, was the evening what you expected?"

"I am not sure what I expected but it was interesting. You know when slut called for the replacement lingerie she promised me that she would do anything if I could manage to free up Anna to deliver it to her earlier today. Since I managed to free up an hour of Anna's time when I was busy, I feel that slut owes me one hour to replace Anna's time, in addition another hour to cover my inconvenience and finally one half hour for processing of a last minute emergency order. That is a total of two and one half hours of her time that I would like to collect at some point. I would require this debt to be paid in full in one installment of time. I would like to know your thoughts on this and what your rules would be pertaining to the repayment."

Rebecca went red and her eyes were going from Marie to me as she listen intently to Marie.

"Slut did tell me about this debt earlier, she felt I had a right to know. My thought are that since slut made the deal, repayment has to be on slut. My rules for the repayment are, first and foremost it cannot involve Rebecca or disrupt her professional life, and no men can be involved. She is not permitted to cum during this time, I do not think Anna did and she was visibly fluster when she got back to your shop after seeing Miss Rebecca. I want to be informed of when everything is set and scheduled. The following probably does not need said, but nothing every really needs unsaid in this game. Complete respect for slut's limits and complete discretion no photo's or digital recording of any kind."

"I agree completely with your rules, slut's limit's will be respected and with the internet now a days I would not let anybody record her, that opens me up to much liability and definitely would violate your primary rule, protecting Rebecca. Not only would I not want to jeopardize our friendship, the fact that Rebecca is a potential customer that needs my help, that is reason enough for me. I look forward to guiding her in changing from a granny to the beautiful successful young business woman that she is without compromising her modesty. One clarification you said no men can be involved what about other woman?"

"Again as long as her limits and safe words are respected other woman can be involved."

"Then as far as you are concerned my proposal is fair payment for services rendered. Slut, Jordan said it is on you to repay your debt of time. I will be in touch next week to schedule your appointment, do not worry my schedule is flexible."

Rebecca gave me a nervous look, I just gave her a nod. She turned back to Marie, "I understand Ma'am, I will have Rebecca check her schedule so I can let you know my availability."

"That will work, one last thing would you explain to me and Anna why you were walking around in your maids outfit with, your panties in your mouth."

Rebecca turned as red as she ever has and took a gulp of her wine refusing to look at anything but the floor.

"I would be interested to know your thoughts on the subject myself, slut, please explain your actions to Marie and include what was going through your mind while they were happening."

Rebecca started in barely a whisper, "Sir"

Slut, look at Marie when addressing her and speak up so we can hear you.

Rebecca's snapped up and looked at Marie, "Ma'am they were in fact my panties from the maids outfit. Jordan was concerned that when he punished me that I would be unable to keep from screaming so he had me get the panties that I had worn all day and he rolled them into a ball with the soiled crotch on the outside. When he pushed them into my mouth I could taste myself, smell myself, it was not pleasant but my thoughts were if this is what I have to do then I will. Sir had me bend over the kitchen table and hold onto the opposite side. He gave me the option to be tide in place or hold on by myself. Sir was right, I was screaming from the first swat with his hand, I was also right I could not have let go of the table it was my anchor to reality. After he finished with the ten swats with his hand he went and got the paddle and the crop and laid them where I could see them and I dreaded what was about to come, then he started with the paddle, I was screaming bloody murder into the panties as he quickly delivered the ten blows. Then he sat down and waited to I was just sobbing before he started with the crop. He swung it a couple of times so I could hear it whistle. Every time I heard that whistle I screamed I was so scared. When the first stroke hit it was like he branded me I howled in pain, but of all of the swats the ones delivered to the underside of my ass felt like he split my skin in two. I do not know how I did not pass out. I was holding on to the table for dear life.

I remember sobbing as he sat there watching me. Once I completely calmed down he just sat there staring at me with me staring back at him, my mind was completely blank. Then he sent me to my room with my dirty panties still in my mouth forbidding me to cum, I was not even permitted to think of anything remotely sexually exciting. I was to take this time to reflect on why I was being punished and what my actions almost cost me, and how I was going to refrain from this in the future. I was devastated, this was my best friend my Sir, I had never felt so alone. It was during this time I began to question how Jordan could be so cold and cruel, and on top of that my pussy was aching for relief and he forbid me any relief. I almost gave up and quick the game, I was sobbing and feeling sorry for myself.

Then my Sir brought me dinner and allowed me to remove my panties to eat. A bit later he came back and let me know that my instructions were on the table and that I should be up early to complete them. Both times I seen concern and sadness on my Sir's face. He also gave me permission to remove the panties while I slept. When he left the room that time I realized he was hurting as much as I was and I started to reflect on my actions and except that I had to figure out what I wanted. After a long conversation with Rebecca, we had made the decision that I was not quitting the game that we both needed it, but we were going to be much more careful. So even though I did not sleep much I was up early as you know by the time of my call to you.

After a while outside of the panties being a nuisance they were not too bad, that was until the groceries were delivered and worse when Anna showed up I was so embarrassed, I think that was my Sir's intention. But the look on Anna's face was priceless. I now know not to try and get Jordan to play outside the game." Rebecca finished and took a gulp of her wine.

I kept an eye on Anna while Rebecca explained her thought on the panties and her acceptance of her required compliance. Even though I know that the severity of Rebecca's punishment disturbed her I could see an understanding in her expression. She also looked a bit too comfortable so I started, "Anna, tonight you have been pushed pretty hard, and I would love to know your thoughts on what was required of you this evening? Start with being exposed at the restaurant"

Marie added to her discomfort, "Yes I would like your thoughts on your actions as well, I want you to answer Jordan's question."

It was Anna's turn to feel the embarrassment of putting her feeling into words, she took a gulp of her wine and with eyes down she started but was quickly cut off by Marie, "Look at Jordan while you answer don't be rude."

Anna raised her eyes to me her cheeks glowing in embarrassment, "When you and Rebecca showed up and she was dressed identical to me I knew Marie was up to something and it was obviously going to involve both Rebecca and I. I could feel a knot forming in my stomach. I only recently met you and Rebecca, I did not really know you and my thoughts were colored by my observations of Rebecca, the marks I had seen at her corset fitting, the way you displayed her at the club, then when I delivered her panties and seen her in the maids outfit and the panties stuffed in her mouth. I was very nervous, I did not know what to expect. Then Marie and you explained about Rebecca's journey and the desire to have me support her by mimicking her action really had my mind running in circles. I watched as you removed the buttons on her blouse and then adjusted it for exposing her charms. Marie stood and did the same to mine then we were permitted to sit. The first time the waiter a complete stranger looked down my top I reacted by coving myself but I watched as Rebecca just sat there and let him look all he wanted. It was obvious she was embarrassed but I also seen her eyes were bright and sparkled.

Then she explained that I had to except that it was not my decision to make and that I to put my trust in Marie and let go. I will say that Rebecca being there helped me. But then you explained that what Rebecca had to do to indicate her acceptance of the game. As I watched her remove her panties and hand them to you, I was having second thoughts but then her eyes met mine and I knew I had to try. Then you just laid the panties on the table for all to see, I was mortified. When we had to give up our bras next and they ended up on the table also. I thought I would die of embarrassment when the waiter came in to serve our dinner, he made no attempt to hide the fact that he was looking down my blouse. If this was not enough now I watched as Rebecca ask permission to comply with your wishes and then stood and removed her blouse and sat back down topless. I can tell you it took all my will and all of Rebecca's help for me to remove my blouse. My mind was going a mile a minute, sitting there with only a curtain between me and being exposed like never before. But at the same time I could feel my pussy tingling and I knew it was a hot mess.

But I would have to say being made to make out with Rebecca was just hot, although having to make out when the waiter was there with the curtain pulled was so humiliating. But having to hold hands when we were sent to cleanup and fix our makeup and to act like we were an item as we left had my mind completely upside-down, I was so humiliated yet my body was ready to explode with need."

"Marie, may I ask Anna another question about her thoughts on tonight? Since she just gave her first real blowjob and got her first real fucking and I would like to know her thoughts."

Marie looked at Anna, "I think that I would also like to know her thoughts on that."

Anna did not hesitate, "I was so nervous that I would disappoint you, but you had Rebecca kneel behind me and encourage me with her words and her touch. I knew then that I would not fail. It was so much different with you, you showed patients you let me move at my own pace. Your smell, your taste the feel of your cock in my mouth it was overwhelming, I could not get enough then Rebecca took a firm hand and pushed so your cock went into my throat. At that point something switched in my head and I wanted it bad and I just started fucking my throat then you told me I had to swallow. I really did not know if I could. Then you went shooting your cum all over my face and in my mouth. I could taste it I could smell it, it was intoxicating but I just could not bring myself to swallow, my upbringing just would not let me. Well that was until Rebecca convinced me to, her words of encouragement and promise of her rewarding me if I pleased you by swallowing your gift of cum. And true to her word she gave me one of the most intense orgasms I have ever felt.

Then you proposed that I should experience a good fucking if I was interested and at that point I had to know, and you did not disappoint me. When you buried you cock in me but would not let me fuck it. It was maddening as you just held it there buried so deep. Once you started actually fucking me I was in heaven, it felt so good I could feel my orgasm climbing then it went off and you started cumming and it pushed my release to the point I think I blacked out.

All I can say is that I hope that I get to experience it again someday."

Rebecca just gave a knowing smirk as Anna made the last statement. Then finished her wine.

"Marie you and Anna are free to stay up and have another glass of wine, you should have everything you need in the guestroom but if you need anything just have Anna knock on my door and slut will get it for you. Coffee and fresh cinnamon rolls in the morning. Slut come with me you can clean up the glasses in the morning. Good night"

"Thank you for a wonderful evening we will be heading to bed also. See you in the morning if we are not up and gone before you get up, Anna has school obligations tomorrow."

With that we all headed to bed for the night. When slut and I got to our bedroom we headed to the shower to rinse off then we climbed into bed. A quick kiss and we both passed out.

When I woke up the next day it was almost 10:00 as the cobwebs cleared I spied my precious slut kneeling in position just watching me. "Good Morning Sir, Marie and Anna have had coffee and have left so Anna can take care of her school work. I can put fresh coffee on for you then help you shower if you would like."

"I take it you slept well last night?"

"Much better because I was beside my Sir and all is right again."

"Very good go start the coffee when you hear my shower start you can come help me shower."

Rebecca stood and headed for the kitchen, I got up went to the bathroom and took care of business. I then started the shower and stepped in, not a minute later slut was there stepping in to help me. She took the washcloth lathered it up and started with my chest and slowly washed every inch of my body. She paid particular attention to my cock and balls which caused my cock to rise. When that happened I pushed her hand away indicating that it was not time for that. After she was done washing me I rinsed and stepped out of the shower with slut following right behind me. She grabbed a big towel and dried me off.