Falling for a Second Wife - Ch. 01

The following is a work of pure fiction. None of these individuals exist nor did anything described actually occur even though I very much wish that some of them could. Some small details have a basis in fact, but not very many.

Background

My wife Susan and I have been married for over 35 years. During that time, we have enjoyed an active and varied sex life together. We have experimented with many positions as well as role swapping and pegging, but we never had an interest in swinging or other forms of group sex activities.

Unfortunately, as we have gotten older, Susan's health has started to slip and she now has problems maintaining her energy levels and she has also lost most of the strength in her legs. Although she still enjoys our time in bed together, her activity level has dropped to the point where I often feel sexually frustrated, depressed and often feel like maybe she doesn't love me anymore even though I know that isn't true.

She understands this and feels guilty about how her health is causing me distress. So she recently came up with an idea to try to help me out that would avoid having to give me permission to seek out an affair with another partner. She decided that she would find a partner for me.

One of her friends, Linda, had recently lost her husband and had told Susan that once she had recovered from the grief, the hardest part of being a widow was the loss of male companionship and sex with a male partner. So without saying anything to me, Susan asked if Linda would be interested in discussing a possible relationship with me.

Linda was shocked by the offer, but said yes. Susan explained that she hadn't said anything to me so that I would need to agree and that Linda would have to follow a number of rules that she would draw up. Susan added that obviously Linda and I would also need to have sufficient chemistry between us to justify having a long term affair. If we could work things out, this would relieve much of the pressure that Susan has been feeling to "treat" my depression through more frequent sessions in bed than her energy levels really allowed. An affair between Linda and I might also help Linda recover from the depression that she said she was experiencing from the loss of her husband.

The following are excerpts from my Journal entries that record my times with Linda.

The Meeting

At the appointed time, Linda arrived at our house and I greeted her at the door. Linda isn't what I would call beautiful, but she is attractive enough to draw my interest. She has very nice tits that I immediately longed to squeeze and has a nice trim waist. She was wearing medium height heels, jeans and a tight blouse that showed off her ample cleavage and upper body. With the heels, her eyes were about at the level of my mouth, so I didn't have to bend over very far to kiss her. We hugged in an embrace that was more sexual than a normal social greeting and then we gave each other quick a kiss on the lips. The chemistry was already there for me and from the look in her eyes; I think that she felt it too.

We moved into the living room where Susan was waiting for us. While I was taking their drink orders, Linda sat down next to Susan and they start talking. After serving their drinks, I pulled up a chair facing them and join in the pleasantries and so that I could continue to look at Linda.

Once we finished with the latest neighborhood gossip, Susan and I both described a bit about ourselves as well as what we would like to see from an affair between Linda and me, beyond just fucking. Linda told us about what she would like from us. It quickly became obvious that we needed an arrangement that went beyond the limits of a simple affair. We also all agreed that we would need to include Susan in some of our sessions.

Susan emphasized that she wouldn't always be able to participate, but that she would enjoy being involved in an occasional threesome and occasionally observing the two of us in bed together. All three of us then proceeded to describe a few of our sexual fantasies. Some of mine are news to Susan. This way each of us got an idea of what we could expect from the others. Linda learned that I really enjoy getting pegged and I learned that in addition to Linda desiring a new sexual partner, her late husband had been abusive, so Linda both wanted a new companion who could be both a tender sex partner as well as a male that would allow her to can direct some her emotional anger at him during sex.

The three of us discussed a variety of sexual relationships ranging from simple two person affairs, to an affair where Susan would observe but not participate to regular threesomes where Susan would be totally involved with both of us. Some options even had Linda assisting Susan to fuck me or for the two of them to fuck each other followed by the Susan and I doing various things to Linda.

We decided that the option that best suited both Linda's needs and mine and that was acceptable to Susan was for Linda to become my Mistress, not my mistress, along with less frequent exploratory threesome sessions.

A femdom relationship between Linda and I would allow Linda to release some of her anger and would not lead to the type of affair that might cause Susan to fear losing me to Linda even though I repeatedly assured Susan that there is no way that I could ever leave her for another woman. Susan and I would continue with our normal sex at night, but less frequently and with more snuggling than we had engaged in recently. That way, would still be getting sex from Susan and domination and rougher sex and pegging from Linda.

As my Mistress, Linda would be able to release some of her anger through the use of any form of physical or sexual assault upon me that she desired so long as it does that does not violate one of the rules that Susan stipulated later. We agreed that during any threesome sessions, Linda would be our joint mistress, not my Mistress, and any activity between the three of us would be limited to "normal" sex, as in no bondage, physical assault, attempts at dominance or unrequested forms of penetration by toys, fingers or my cock.

Then we discussed each of our schedules. We finally decided that Linda and I will get together after lunch each Wednesday and that assuming that Susan's health and energy levels allow, all three of us will get together once a month on a Friday afternoon. Linda and I will forego our session on any week when we have a threesome with Susan since we both wanted to be able to direct all of our sexual energy toward Susan during the threesome sessions.

If Linda or I developed a conflict for our normal Wednesday sessions, we agreed to text each other ASAP to find another time to get together. We all viewed all of these sessions as too important for each of us to allow any cancellations.

The combination of Wednesday dominance sessions and monthly threesomes would allow Susan to know how to adjust her schedule to get enough rest ahead of time to be able to actively participate in our threesomes. That way, she would not simply lie in bed receiving our the attention and just get fucked by Linda and me without an opportunity to fuck one or both of us. Skipping Wednesday sessions before a Friday threesome would also leave both Linda and me so sexually frustrated by Friday afternoon that Susan will most certainly get more fucking than she expected the first time around.

Therefore, we all agreed that this would not be a simple affair between Linda and me. It will consist of the weekly femdom and fucking sessions between Linda and me to satisfy our needs and monthly threesomes so that Susan would not be left out. Susan is also allowed participate in any of Linda's dominance sessions when she wishes or when Linda requests Susan's presence.

It was further agreed that when Linda arrives for a session, the two of us are allowed a tight embrace at the door along with a kiss on the lips and any physical groping that either one of us desires to bestow on the other. I will be allowed to address her as Linda and to act as a gentleman doing things such as helping her with her coat, carrying any bags, assisting her up the stairs to the bedroom, etc.

Susan is also allowed a hug, kiss and to grope Linda, if she so wishes but Linda has to ask Susan's permission for anything more than a kiss, butt pat or tit squeeze. Once Linda and I are in the bedroom and close the door, I am only to address Linda as Mistress and must immediately follow all of her commands. I must also follow any directions that she has texted to me prior to her arrival as if we were already behind the closed door. This can include commands such as donning whatever attire she requests, cleaning out my ass to prep for pegging or preparing any toys that she requests to be ready upon her arrival.

Finally, we all adjourned to the bedroom so that Linda could see the collection of toys that I have accumulated and that she will be able to use on me whenever she wishes. Linda also looked through my clothing and shoes and through Susan's clothing, shoes and jewelry. Linda did this so that she could get an idea of what she can ask prior permission to have me wearing upon her arrival.

I am not a cross dresser, but I understood that Linda would occasionally wish me to do so. Linda asked me to try on a couple of Susan's shoes, skirts and bras to get an idea of what fits me and what does not. Fortunately, Susan and I are about the same size, so most of her clothing fits reasonably well. Linda seemed especially interested in a pair of Susan's 5-inch stiletto sandals that I am able to wear. She asked me to take a few steps and was very impressed that I can walk in them without wobbling around too much or falling and breaking my ankle.

Susan then laid down her rules for our relationship. They are as follows:

Susan's Rules

1. Kissing is limited to kissing on the lips or gentiles. French kissing is only allowed during threesome sessions or after Susan has bestowed her blessing.

2. Under no circumstances can I put my cock in Linda's pussy unless Susan is present and gives us verbal permission

3. The relationship will be one where Linda will be dominant and I can be subjected to any form of physical or sexual assault that she chooses that does not violate Rules 8, 9 and 10

4. The relationship can include any form of physical and sexual assault that Linda desires. No form of emotional or psychological assault is permitted at any time by either of us. This is important because Linda's late husband was emotionally abusive and was very controlling

5. No drugs of any kind will be used by either of us except those prescribed by a doctor. This means no weed, alcohol, Viagra, etc. before, during or after our sessions

6. I will be required to use a condom anytime that my cock enters Linda's body other than during oral sex. This includes during threesomes. Linda will be required to use a latex glove anytime that one or more of her fingers enters my ass. Also, neither of us is allowed any form of ass-to-mouth play although rimming is permitted.

7. Linda is allowed to provide any equipment she needs to satisfy her desires. She is also allowed to use all of my toys, any of my clothing (which cannot be damaged) and any of Susan's clothing provided she has prior permission to use Susan's things.

8. Linda is not allowed to cause me any type of physical injury. This includes anything more than a small bruise. Injury includes things like fingernail scratches, cuts, etc.

9. Linda is not allowed to leave a mark anywhere on my body that will be visible 12 hrs later

10. Linda is not allowed to leave any mark on my body that cannot be covered by clothing that is suitable for the season. This means that nothing can show as soon as I get dressed.

11. When Linda arrives for a session, we are allowed a hug and a kiss at the door and I am allowed to address her by name. Once we are alone and close the bedroom door, I can only address her as Mistress.

12. If Linda violates any of these rules, roles will be reversed at the next session and she will be subjected to any form of physical or sexual assault that Susan and/or I choose that is within the same rules that she is subject to.

13. Our relationship can be terminated without notice at any time by either one of us and no reason for the termination is required.

Session 1 -- Linda's Introduction to Our Toy Collection

Today was my first session with Linda. Yesterday, I received a text that said that she wanted to learn how to use my entire toy collection, so I should clean out my ass as preparation for a long pegging session. She also asked me to tell Susan that she would need her help.

This first session was essentially a training session for Linda. She had asked Susan to join us in the bedroom because she wanted Susan to demonstrate the use of all of the toys in my collection. As soon as the bedroom door closed behind all of us Linda ordered me to strip from the waist down. While I was removing my clothes, Susan showed Linda our toy drawer and got out a towel and spread it on the bed for the used toys.

While Susan was doing this, Linda removed a bottle of lube and the two of them took all of the toys from the drawer and put them next to the towel. Susan then proceeded to describe to Linda how to lube each type of toy, how to turn on the toys that contained vibrators, to change batteries or recharge the ones with power and how to use the remotes for the two toys that have them.

After Susan had finished describing how each toy or remote control worked, I was given a chance to explain to Linda how each toy felt and the benefits and limitations of each. For example, one toy that is very thin and about the length of my rectum has a hard, fairly sharp tip. So Linda would need to be careful not to push it in too far unless she wanted it to cause pain. Limiting how far she pushed it in would also decrease the chance of it getting lost in my ass, which would necessitate an abrupt end to our session and a trip to the Emergency Room.

In contrast, another toy is only slightly longer that the first and appears to be the same length until they are placed side by side. The second toy initially appears to be much larger because it is larger in diameter and has a rounded, blunt tip. I explained that instead of causing pain when forced into my ass, this toy is actually quite comfortable when pushed in to its limit. Also, because it is just a bit longer, it cannot be pushed in far enough to get lost in my ass, at least not without the use of unreasonable force. I explained that it is actually comfortable enough for me to insert it in my ass and then to sit on it while I work.

I went through the pros and cons of the rest of the toys and ended with an explanation of the largest toy. This is a conical dildo that is about seven inches long and three inches in diameter at the base. It has spiral groves down the side that require extra lube and it also has rather sharp points near the base that point upward and are painfully when they hit my anal sphincter. This toy also has a suction cup base that is perfect for attaching to the shower wall or is a comfortable place for my partner put a knee on to push harder. I said that if she wanted to just sit and watch me fuck myself, this was the best toy for that purpose.

Susan then decided that we needed to make things more interesting than simply having them fuck my ass with each toy. She suggested to my Mistress (I had no say in the matter) that we would play a game. I would wear a blindfold, ear plugs and noise reduction earmuffs so that I could not hear their plans for my ass or their conversations. They would then randomly select a toy and fuck me with it for as long and hard as they wanted. I would then have to identify the toy based upon the way it felt in my ass. Since they would be able to repeat the use of any toy at any time and could fuck me with a toy for any length of time, I would get a slap on the ass to let me know when they were finished fucking me with that toy and moving on to the next one.

If I correctly identified all of the toys by the time that they had run through all of them, my reward would be 15 minutes of fucking using a double lobed butt plug that feels really great but is intense due to its size. If I miss-identified just one toy, they would take the largest toy, the seven inch conical cock with the grooves and sharp points near the base and then DP me with it by also pushing one of the smaller toys into me using one of the grooves.

They didn't define smaller, but I wasn't going to bring this up since my word meant nothing right then and I didn't want to give them any ideas. Getting DP'd with the conical cock and even one of the smaller toys would be both sexually intense and very painful since even the conical cock has the potential to stretch my asshole past its limit. So that would definitely be a penalty for any error on my part. Further, my penalty would allow them to tag team fuck me like this for as long as they wished and to switch out the smaller toy for another other small toy whenever they wanted.

I inserted the ear plugs, put on the noise reduction headset, got on my knees at the edge of the bed, donned the blindfold and then put my hands on the bed. It seemed like forever before anything happened. I assume that they were discussing which toy to use first and the progression through the collection plus giving Linda a chance to learn to lube up the first toy and probably said things to make certain that I couldn't hear them.

I finally felt a cold finger on my asshole as lube was applied and the lubed finger was pushed in a little and then one of them, I assume Linda, started fucking my ass with the first toy.

Toy Progression

The first toy they used was one that I call the pencil dick. It is a long thin, hard plastic toyk that is about the diameter of a fat pencil with about a dozen small ribs that run along the length from near the tip to near the base. It has a dull but pointed tip and its length is about the length of my rectum. As a result of being my shortest toy, if pushed too hard it might get sucked into my ass. But it also causes pain when pushed that hard since the small tip is probably pushing into the end of my rectum.

Once inserted, if twisted back and forth, it feels a lot like my asshole is getting rimmed. Normally, I don't use this toy very much because of the risk of pain and also because it is so thin that I don't really feel like I am getting fucked. It is therefore only good for rimming and I have toys that do a better job of that. So, the size of the pencil dick made it easy to identify to my Mistress.

The second toy is one that I call the green probe. Obviously from its name, it is green and it was purchased as an anal probe. It is quite a bit longer than the pencil dick at seven inches total length of which about five is insertable. It has a smooth, almost satiny hard plastic surface and widens from a rounded point that is only a bit less sharp than the pencil dick to a diameter of 1.25 inches that is about 2/3 of the way from the tip to the handle. At that point, it tapers back down to about a half inch before reaching the handle.

As a result of this taper up to the shoulder and then back down again, my ass tends to suck it in once the shoulder passes through my sphincter. It is also long enough that when my ass sucks it in and the narrowest part of the neck is held by my sphincter, the point can sometimes cause pain similar to the pencil dick, but usually not. It probably depends upon where the tip hits in relationship to the turn toward my sigmoid colon.

Another property of the green probe is that it has a strong vibrator at its widest point, which does a fantastic job on my prostate. Susan even loves to occasionally use this vibrator on her clit because it is so strong and its length makes it easy for her to hold. For me, it also feels great to have the shoulder cycled back and forth through my sphincter. That gives me a great feeling of being fucked, especially if it is moved in and out very quickly.