The Vacation Pt. 02

Chapter 2: Guess who's coming to dinner

I greeted Shirley with a kiss as she extended the back of her hand towards me. This was my normal greeting as I waited for her kneeling in the entry way. My cock was locked in the chastity belt with a medium sized butt plug lodged in my ass. I was naked and my knees hurt from the prolonged period of kneeling.

"Honey, I'm home." She announced as she opened the door. "This is Barbara, my supervisor from work. You've heard me talk about her before. Her apartment is being painted so she needed a place to stay this weekend. I invited her to stay with us so it looks like you'll have two women to serve this weekend. I believe that was one of your fantasies wasn't it?"

I did remember our conversations about Barbara. She was new to the company Shirley worked for. In the beginning they had their difficulties. Barbara was ex-military and she expected everyone to jump to her every command. She tended to micro-manage the department and always questioned the employees about what they were doing and why. This was a lot different from Shirley's previous boss who was more laid back in her supervisory role. I figured Barbara's demeanor was a result of her 20 year career in the Marine Corps.

Shirley and Barbara had worked out their differences after having an intense squabble several months ago. I hadn't heard much about Barbara since that incident but assumed they had developed a friendlier relationship. I didn't realize how much so until now.

Barbara was a large woman. Most would call her a SSBBW. I guessed that she weighed over 350 pounds. Shirley told me that Barbara had been married twice before, each ending in divorce. She had won a large settlement following the second divorce and between her income from her Marine pension and her divorce settlement, had not needed to work. Shirley explained that Barbara was devastated when her second husband ran off with another woman. Barbara's self-esteem had been shattered and in her depressed state had gained nearly 200 pounds. In an effort to retake control of her life, she decided to reenter the workforce.

I guessed Barbara was about 5'10" as she was a couple of inches shorter than my 6' frame. She carried most of her weight around the hips and abdomen. She also had massive breasts which sagged noticeably. She had thunderous thighs and I was certain that she would make any chair squeak under her weight. Her face was somewhat attractive and her hair was short and curly; typical of someone who had spent their life in the military. I guessed she was of Italian or Mediterranean descent based on the olive tint of her skin. She wore a dress came to just above the knees and I imagined it was a size or two too small as it was barely able to contain all of her mammoth size. I was waiting for it to burst at the seams at any moment.

"Honey, you're not showing proper respect. I think you should greet Barbara in a more appropriate way." Shirley said. "Kiss her hand like you do mine and ask her if you can serve her this weekend."

Barbara smiled as she held out her hand for me to kiss. She held it longer than Shirley had so I continued to kiss it until she withdrew it. Barbara seemed satisfied and agreed to allow me to serve her. The entire time she was staring at my crotch with the look of a woman who hadn't had sex in years. Judging by her appearance, I suspected she hadn't.

After kissing her hand I realized how exposed I was and immediately tried to cover up.

"No need for that honey," Shirley said. "I think you've already shown her all you have to offer. Now, is dinner ready? We're famished."

"It will be in a few minutes." I replied. "I didn't know what time you would be home so I just have to put it on the table. Would you like some wine while you wait?"

"That sounds wonderful," Barbara said. "Can you also bring my things in from the car? I have several bags in the back seat. Shirley, can you show me where I'll be staying. I want to freshen up a little before dinner."

Shirley told me to put on some clothes and do as Barbara requested. It took two trips to fetch all of Barbara's things. It seemed a little excessive for a weekend stay but I was not about to say anything at this point.

Dinner was ready by the time I finished my assignment. The ladies sat down as I served it. I joined them when I was sure they had everything they needed. The meal started off rather quietly with both women staring at me. I ate in silence for a few minutes hoping their stare did not mean I was in trouble.

"Dean," Shirley finally said. "I believe you forgot to strip when you came back inside. I think you had better do so now!"

We ate our dinner. It was like we had been friends for years. We talked about family and friends and I learned that Barbara had four children, all girls. Three had been from her first marriage and were raised by her mother while Barbara remained on active duty. The fourth child was a surprise from her second marriage. Barbara had raised her after retiring from the military.

As we continued to chat Barbara came up with an idea. She said that she owned a beach house in South Carolina near Myrtle Beach. It was a large house that was part of her divorce settlement. She said that she spent weekends there during the summer whenever possible and that her youngest daughters lived there while attending college.

"Shirley," she announced. "I think we should all head down there for a week as a reward for all the long hours we put in over the summer. There is plenty of room for you and Dean and I would love for you to meet the family. How does the third week in September sound? It's still warm there and the water is wonderful that time of year."

"That would be great Barbara." Shirley replied without even asking my opinion. "I love the beach and you're right, we do need to get away and relax."

"It's settle then." Barbra said. "I'll make all the arrangements. In a couple of weeks we'll be heading south for some fun in the sun. Say, why don't we go shopping tomorrow? You know, part of the fun of going on vacation is buying some new clothes for the trip."

They continued to talk about the upcoming trip and how fun it would be to have someone wait on them hand and foot while they took in the sun on the beach. I felt left out as I wasn't included in the conversation. I wasn't even asked if I wanted to go. I was starting to pout just a little. Our 30 day experiment with a FLR was supposed to end tonight and here I was playing the servant to two women, one I hardly knew. Furthermore they were making plans that included the possibility of me serving them while on vacation." Finally I had enough and spoke up.

"Shirley, we need to talk." I said.

"We can talk after you clear the table and clean the kitchen." Shirley replied. "We'll be in the living room."

I did as she requested. It was nearly 10 pm by the time I was through and the women were still busy discussing the upcoming vacation.

"Dean," Barbara said. "Bring us another glass of wine. My glass has been empty for 10 minutes. You really must do a better job serving me. After all, you did ask to be my servant for the weekend didn't you?"

"Yes Ma'am" was all I could reply.

When I returned with their wine they ended their conversation and looked at me.

"You had something you wanted to discuss?" Shirley said.

"You know our 30 day trial period ends tonight." I began. "It appears to me that you assume that the current arrangement is going to continue indefinitely. You haven't even asked me if I wanted to go on this damn vacation. You just assume I will continue serving you as I have for the last 30 days."

Shirley was taken back a bit by my comments. Barbara just looked at me.

"OK Dean, lets discuss it here and now." Shirley replied.

I told her how I felt about the current arrangement. I told her I loved her and enjoyed serving her, especially playing some of the BDSM games, but I didn't think I could keep it up 24/7. I told her that some of the things I had fantasized about no longer interested me, while others I actually enjoyed and would like to continue. I told her I wasn't sure I wanted to continue."

"Let's get a couple of things straight." She replied. "I have come to enjoy this relationship. With Barbara's guidance I now know the benefits of a Female Led Relationship. When I first moved in I was always having to clean up after you. Working 50 or 60 hours a week plus my commute was bad enough, but having to take care of all the housework was just too much. Over the last 30 days I have been able to relax when I get home and the occasional discipline sessions has helped to relieve a lot of the stress I feel from work. I also think you have enjoyed the last 30 days more than you realize. Hasn't the sex been great?"

"Yes, but..." I replied.

"No buts. You have tried to have an erection all night tonight, despite everything that has occurred. If I took that chastity belt off of you right now I guarantee you would be hard as a rock in seconds. Can you deny what your cock obviously knows?" Shirley asked.

I stood in silence contemplating what she had said.

She continued. "It was your fantasy to serve two dominant women. You know it has been difficult for me to discipline you during the last month. I love you and don't want to hurt you. Barbara's demeanor at work and her dominant personality led me to seek her help so you could live out your fantasies. I wanted to do this for you, but as the days passed, I began to enjoy it myself."

She continued. "It was Barbara who mentored me over the past month. It was also Barbara who suggested the camera system and the chastity belt. It was Barbara who suggested some of the potentially humiliating situations that you had to endure but obviously enjoyed. They were all on your list of fantasies or things you or we have discussed doing."

I continued to listen; unable to debate any of the points she made.

"I felt I needed to do something to repay Barbara for all her help." Shirley added. "She mentioned that she wished she could find someone as devoted as you to serve her so I offered her your services for the weekend. It was another of your fantasies, although you probably had someone like the college girls across the street in mind. Now you say this is not what you want. Guess what. It's what I want."

Shirley thought for a moment before continuing. "Yes, I told you we would discuss the arrangement after 30 days, but I never told you that you would have a choice whether it continued. If you remember, I told you to be sure this is what you wanted before we began. You assured me that it was. Now I am just as sure that I want it to continue."

We took a break for a few minutes. I needed to think and Shirley needed to cool down a little. I loved Shirley and would do almost anything for her. Did I really want to continue to live my fantasies, and if so could I give total control of my life to someone else?

It was Barbara who came up with the answer.

"Let's let his cock decide." She announced. "I suggest that we let Dean out of his chastity device. We will give him time to regain his composure and lose any erection that might develop. I think a cold shower should do the trick. When he says he is ready we will give him a test. We'll use the list of BDSM activities he completed last month. I will read each activity on the list and we will evaluate the reaction of his cock to each item. If Dean responds by getting an erection we will know that activity excites him. If his cock twitches or starts to harden, that will also indicate the activity is something he might enjoy doing. If his cock doesn't react or deflates we can assume the activity is not something he would enjoy."

"Ah, I'm not sure about this. I'm pretty worked up having been in chastity for a week." I said.

Barbara continued. "That's the point. If chastity has made you horny, then we can assume it is something that excites you."

She looked at the list for a moment.

"If the activity involved sucking another man's cock, I would expect your cock to deflate a little. Maybe not completely, but there should be some indication to indicate that activity is not something you would enjoy. After all, you listed it as a hard limit."

"I guess I see your point." I replied. "But my cock might not respond instantaneously, especially if I am still thinking about a previous activity that might have excited me."

"Good point." Shirley interjected. "I suggest that we start with the activities that he scored the lowest. That way we'll evaluate his hard and soft limits first, before any of his other fantasies have an opportunity to excite him. We should allow him 30 seconds to consider each item. That should be ample time to allow his cock to react."

"OK." Barbara said. "30 seconds per activity. If less than 75 percent of the activities excite him then we can assume a FLR would not be a good choice. You could still play on occasion, but that is something you both will have to agree on. Now, if he scores between 75 and 85 percent, it would indicate that Dean still has some interest in a FLR but maybe not enough to want to commit to it 24/7. I think it should be up to him if you continue down that avenue. If he scores 85 percent or more, I think it is obvious that Dean still has interest in serving a dominant woman whether he wants to admit it or not. In that case Shirley gets to decide if your FLR continues. Is that fair?"

"Can we set a time limit?" I asked. "Maybe one year and then reevaluate."

"Sure" Shirley replied. "Honey, whatever the decision, I think you still need to serve Barbara this weekend. After all, she did help make your fantasies come true."

I thought for a moment. I really didn't mind serving a large woman. After all, Shirley had gained considerable weight and now was about 220. Barbara on the other hand was much larger than anyone I had considered serving. I once played with a woman who weighed 260, but Barbara topped that by another 100 pounds. After a lot of soul searching I finally agreed and to show my respect, kneeled down and kissed Barbara's feet.

We all agreed to the rules of the contest. I knew it would be a challenge to remain flaccid after a week without masturbation, but I hoped a cold shower would help. About 30 minutes later I was standing naked before both women. Wrist cuffs were placed on each wrist and connected together behind my back. A spreader bar was attached to ankle cuffs which spread my legs widely. I was fully exposed with my cock hanging softly between my legs.

"We just want to make sure you are fully exposed for our evaluation." Barbara said as she began reading off the list of activities.

She started with my hard limits. As she read I continued to remain flaccid. Normally she would announce the activity and if appropriate, its definition. She would wait 30 seconds and then announce the next activity. Occasionally she would combine several similar activities into one item. If my cock stirred, I earned points for all of the activities mentioned.

Even with her combining activities it was nearly midnight before I finished the test. Barbara totaled the score then handed the activity list to Shirley. She verified the math and passed it to me. We all concurred that I scored 84%. The score was higher than I expected, but it did confirm that I still fantasized about serving a dominant woman. I hoped my fantasies wouldn't betray me over the next year as I got on my knees, kissed Shirley's feet and begged to be her servant.

Shirley looked down upon me and wiped the tears from her eyes. I knew no one had dedicated themselves to serving her like this before; not even during her two previous marriages. I could tell that she was touched by the moment. She accepted my offer and told me to rise.

It was now after midnight and we were all spent.

"It's been a long day and I think we should retire for the night." Shirley said. "Honey, tonight you will sleep with Barbara but first I want you back in your chastity belt. I'm not ready to give anyone access to your cock. That belongs to me! Tomorrow is going to be a long day. Have breakfast ready for us at 9 AM. You've earned a discipline session which we will take care of after breakfast. I would recommend that you serve Barbara well tonight as she will definitely participate in your punishment session. After lunch you will accompany us while we go shopping."

Shirley handed Barbara my chastity belt which she immediately applied.

"No need for the butt plug Shirley." Barbara said. "I have some other uses for that hole. See you in the morning. Come along slave dean, I've got plans for you tonight."

Barbara turned and started towards the stairs that led to the bedroom. She turned to look back at me and told me to get on my hands and knees and crawl. Shirley looked on and was amused by the sight of me crawling on hands and knees.

"Have fun you two." She said as she headed to the master bedroom. "See you in the morning."

Shirley was gone by the time I had crawled to where Barbara was standing.

"Now that she is gone we can get better acquainted." Barbara said. "Crawl up behind me and stick your nose up my butt. This is how you will follow whenever I tell you to heel. You will earn a punishment each time you fail to keep up."

I crawled behind her and pushed my face into her ass. She immediately bent over and reached to spread her ass cheeks apart.

"Push harder." She said. "Your entire face should be buried in my ass. Yes, that's better. Now follow me up the stairs."

It was difficult to keep up with her as I crawled along. I literally had to push her on her way to remain buried in her derriere. The stairs were exceptionally difficult. Three times I failed to keep up with her.

"That's one punishment." She said. "That's two... That's three."

We finally reached the spare bedroom. I saw that she had already applied restraining straps to the corners of the queen sized bed. Lying on the night stand next to the bed were an assortment of paddles, whips and several canes. What bothered me more was the strap on harness and assortment of dildos she had laid out for me to see. There was fear in my eyes which she noticed immediately. She also noticed my cock straining to get out of its cage.

"I guess you've figured out I've done this before." She announced. "My mom was a very strong willed woman. She ruled the household with an iron fist and she taught me and my two sisters that we had to be assertive if we were going to survive in a man's world. She didn't beat my dad but she sure controlled him. When I joined the Corps I realized what she said was true. I had to be better and tougher than any of the men I commanded. I learned a lot about controlling others. Many of my subordinates called me the 'Bitch Captain' and for the most part they were correct. I squashed anyone who got in my way. I ended up retiring as a Lieutenant Colonel."

"We can talk more of that later." She said. "Right now I need your face buried in my ass. You might say I'm a very anal person but I'm sure you'll figure that out for yourself."

She secured me spread eagle to the bed. I was face up with my head at the foot of the bed. When she had finished securing me she began to strip. As she stood before me she reached out to stroke my cock. As she expected, my cock stained against its imprisonment. She turned and lowered herself onto my face as she sat on the bed.

"This is your first punishment." She said. "You will lick my asshole until I orgasm. Fortunately for you I am already wet from tonight's activities. Reading that list of BDSM activities got me hot, and when you volunteered to serve Shirley, I almost came. I am going to continue to mentor her and by the time I'm done, you will be a perfect slave to both of us."

My world went black. I struggled to breathe as Barbara spread her cheeks once again and squirmed around until I found her puckered hole. She occasionally gave me an opportunity to catch a breath of air but only when she felt I was going to pass out. Whenever my worshipping of her ass began to falter she would bear down against my tongue and remind me that toilet service was no longer on my list of hard limits. The threat was enough to motivate me.
After about 15 minutes Barbara started squirming more on my face. She was beginning to gasp for air and her moaning increased. She was rubbing her ass up and down across my face to create more friction. All I could smell was the musky fragrance of her ass. Barbara was panting now. I knew she was prolonging her climax as long as she could. I jabbed her hard with my tongue and she moaned in delight. I just wanted to get this over with and her off my face.

She finally climaxed. I was drowned in her juices. Her entire weight bore down on my face as she lost control of her body. It lasted for what seemed like 5 minutes but was probably closer to 90 seconds. When she was finished she gave me an opportunity to catch my breath.

"Clean me up now." She said as she planted her pussy over my mouth. I licked her clean. It was as unpleasant as licking her ass had been. When I was done she spread her legs a little further apart.

"I think golden showers was one of those Fantasies that made you erect earlier." She said. "Welcome to reality."

I felt the first gush of warm spray hit the back of my mouth. I couldn't avoid it. She controlled the flow, stopping when necessary to ensure that I swallowed all she had to offer. When she was done she got up and unfastened the straps securing me to the bed.

"Better get used to that." She said. "I use to really enjoy watersports. I haven't done it in a while but it really felt good and your tongue is much better than toilet paper. Cheaper too."

She had me turn around and roll over. She took the pillows from the bed and put them under my midsection and then secured me to the bed again. My ass was now raised and I knew what was coming next. I wasn't looking forward to it. She donned her custom made harness and put a medium sized dildo through the retaining ring. It was about 2 inches in diameter and 8 inches long.

"I understand you have some experience with this." She said. "I think we can skip the beginner models and move on to something a little more challenging. Shirley tells me you keep begging her to fuck your ass. When I get done with you you'll be begging in a different way."

She lubed her cock and my ass before positioning behind me. She wasn't very mobile but she certainly could provide enough force to get the job done. She positioned the cock so it just penetrated my ass. She then let her weight do all the work as she slowly impaled her phallus until it was embedded all the way in my hole. She slowly started pumping with the bed creaking each time she moved. I wondered if Shirley heard it in the next room and knew what was happening.

She pumped for about 15 minutes and then took a break. Her weight on top of me made it difficult for me to breath. After about ten minutes she began again. She reached under her and found my nipple. I winced in pain as she squeezed one and then the other. She fucked me a total of four times over the next 90 minutes. When she got up she looked down at her cock.

"Bitch" she said. "Look how dirty you got my cock. I think you have earned another punishment. We will discuss that in the morning. Take it and clean it then return here. I'm going to bed. You can sleep on the floor."

It was after 3 am when I finally got to lie down. Although I was tired I had trouble falling asleep. My cock hurt from its confinement and my mind continuously replayed the night's events. I finally drifted off only to be awoken at 7 am by Barbara who once again had to pee.

Chapter 3: The weekend continues (Coming soon)

the vacation

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