Retirement Living

Chapter 3

In chapter 2, my wife Sharon and I were introduced to swinging by our threesome fuck-buddy Martha and her new husband, Jim. During our final ménage-a-trois with Martha, Sharon and Martha expressed the desire to see me with another man. They resurrected this idea once we all started swapping and the girls pressured Jim and me until we eventually came to a compromise that called for Jim and me to blow each other's cocks while they watched. The girls still were not completely satisfied because they wanted to watch us fuck each other's ass, but Jim and I were adamant that that would probably never happen.

Six Months Later

Sharon and Martha have subtly kept hinting and needling us that they really want to see Jim and I fuck each other in the ass. Jim and I have resisted because neither of us finds the idea particularly attractive. Jim and I would rather continue swapping wives and occasionally joining together for a foursome session that was restricted to swapping partners and sometimes letting the girls put on a show for us.

Finally, yesterday I had have enough of Sharon's hounding me about wanting to watch me get fucked by Jim and I told her that I would agree if she would agree to my conditions, would share them with Martha and provided that Jim also agrees.

I explained to Sharon that you regularly accept my cock or Jim's cock into your body, almost nightly. But I have never asked you to take me up your ass. Further, Jim and I have never experienced any form of sexual penetration by anyone else other than the one time that we reluctantly blew each other's cocks. Besides, if we go through with your idea, it complicates my life every time that I have to go to a doctor because one of the standard questions men get asked is whether you ever had penetrative sex with another man. If I say yes, my doctor will insist on giving me an HIV test and I will be banned from ever donating blood again.

My Conditions:

• I get to fuck you in the ass anytime that I want for the next six weeks. I agree to start easy but promise that near the end, I will be forcefully fucking your ass. If you feel this hurts too much, you can call the whole thing off at any time. Similarly, if Martha decides that she cannot take Jim's fucking her ass and calls it off, the whole thing is over. Further, if we get past the first six weeks, I can continue to fuck your ass after the six week period any time I want for as long as I want.

• If you (and Martha) are still interested after the six weeks, you will buy a lifelike dildo that closely matches the size of Jim's cock (you can measure him during one of your stays with him). If you want to get a strap on harness to use with it rather than using your hand to peg me with the dildo, that is your decision.

Then you will peg me once a week for the next six weeks to help me get used to the feeling of having something as big as Jim's cock in my ass. You will start with slow, shallow penetration to allow me to get used to the feeling of taking something foreign up my ass. You will gradually increase the depth and speed so that at the end of six weeks you will be rapidly fucking me balls deep. If I feel that it hurts too much, that will be sufficient reason for me to call an end the "experiment". The whole idea of this is to prepare my ass to be fucked by Jim.

• At the end of all of these "practice" ass fucking sessions, if none of us have called an end to the experiment, Jim and I will meet privately again to decide whether we want to provide you with your show or if we would rather tolerate the two of you continuing to pressure us. If we decide to go through with it, we will decide on the details of how it will be done and what your role(s) will be.

• If any of us calls a stop to all of the experiment, both of you (Sharon and Martha) agree to never bring the matter up ever again.

I printed off two copies of this and gave them to Sharon. One copy was for her and one was to give to Martha. We didn't hear anything from Martha or Jim for two weeks until Jim brought back a marked up copy the printout. He said that they had discussed them at length and that he wanted to change both of the six week times to eight.

Since Sharon wasn't there, he told me that he was going to fuck Martha's ass as hard as he could during the first six weeks to try to convince her to give up the idea. I thought that this was great since I was pretty sure that Martha had been the primary driver for the pressure that we had both been under.

He had also added a condition that the dildos that Sharon and Martha would be purchasing should be different colors so that they couldn't get mixed up in the future. He conceded that our wives would probably fall in love with the control aspect of being able to peg us, so we should accept that and would therefore need to be able to keep the two dildos from getting mixed up.

He added that Martha was fairly sure that she was going to get a harness, so I should be prepared for Sharon to bring one home too.

His final addition was that if the two of us end up having to fuck each other in front of our wives; that they had to be prepared for us to fuck the other's wife in the ass afterwards while the other couple watched. So, Jim would fuck Sharon's ass while Martha and I watched and I would fuck Martha's ass while Jim and Sharon watched.

My First Session with Sharon

I explained to Sharon that anytime that I tell her that I am going to fuck her ass, she must immediately go into the bathroom and fill an enema bulb with water. She must then lube the tip of the bulb's nozzle and her asshole and then inject the entire contents of the bulb into her ass. She should then hold the water in her ass as she washed the bulb and nozzle with soap and hot water. Only after she was finished could she void her ass of the dirty water.

Then I added that I ever felt anything inside her ass as I am fucking her, I would immediately take her into the bathroom and repeat the procedure myself except that I will place her on her knees with her head on the floor so that I can be sure to empty all of the water out of the bulb and that the water would be warmer than body temperature but not hot enough to cause damage.

I said that during this first session, I will push two fingers into your ass to help open you up and to get you used to having something in your ass. I will rotate my fingers to loosen up your entire asshole and then pull out I will then do the same thing with three fingers in the shape of a triangle. After rotating three fingers around I will spread them into a line and rotate them again to further open you up. I will remove then my fingers and will then slowly push the head of my lubed up cock into your ass.

Once the head is in and your asshole has closed around the shaft of my cock, I will hold it there to let you get used to it. Relaxing your asshole as I do all of this will help reduce the initial pain of penetration. If you decide that the pain is too much, you are free to tell me to stop, which ends everything for both couples.

Then, once I have let you get used to having the head of my cock inside your ass, I will slowly push until my entire cock is inside of you. I will again stop to allow you to adjust before I start to slowly fuck your ass. I will take it easy on you the first time around. I asked

"Do you still want to go ahead?"

And she replied yes.

I finally said, I am not going to ask you right now, but you will never know when I am going to fuck your ass until I tell you to head for the bathroom.

The next afternoon, she didn't appear to be too busy, so I walked up to her and said

"I want to fuck your ass right now. Go clean yourself out and prepare yourself for your first ass fucking."

She asked right now? To which my reply was that

'Our agreement says that I can fuck your ass anytime that I want and I want to shove my cock into your ass right now. Now go get ready."

When Sharon came into be bedroom, she was only wearing a blouse and her panties. I told her to take off her panties and to bend over and place her hands on the edge of the bed. I then knelt behind her and lubed up my fingers. First, I ran a finger around her asshole to get it lubed too. Then I pushed my index finger into her until I my knuckle was against her asshole. I told her that this was one finger and that I wanted her to first get the feeling of having her ass penetrated.

I pulled my finger out and then inserted my middle finger up to my knuckles along with my index finger. This time, I wiggled my fingers around inside her ass and rotated my wrist so that my fingers rimmed her asshole. After about a minute of this, I pulled out and inserted three fingers in the shape of a triangle. I let her get used to the feeling of the extra volume before wiggling my fingers again. Then I spread my three fingers out into a line to stretch her asshole. She let out a gasp, so I asked if she was in pain. She said that she was okay but that she hadn't expected to be stretched that much. I told her, just wait because my cock head is going to stretch you even more.

At that point, I told her, remember that you can call this off anytime you want. I pulled my fingers out so that only the first joint of each finger remained inside of her and then spread my fingers as wide as her ass allowed. She gasped again and then said to proceed. So, I rotated my wrist again so that I could stretch her asshole in every direction. This time her ass was opened up to about the size of my cock head. As I was doing this, I pulled my fingers out a little bit more so that I could increase the distance between my fingers as much as her ass would allow. After rotating my wrist a few more times, I let my fingers move back into a triangle and then pulled out.

At this point I asked her if she still wanted to proceed with taking my cock up her ass. She said that she was okay and to proceed.

As I lubed up my cock, I told her to climb into bed face down. Then I crawled up with my knees just below her knees and told her to reach around, grab your butt cheeks and spread them for me. Since I had already lubed up her asshole, I touched the tip of my cock to her asshole and paused. I reminded her to relax her asshole to reduce the pain. I said if she strained as if she was trying to shit, that would help her open up. I waited for a second and saw her asshole open up a bit, so I pressed my cock in until her asshole had closed around the head. She gasped and said

"That hurts"

So I asked if she wanted to stop and she emphatically said no. So, I waited a bit for her to get used to the feeling of having her ass violated and then slowly started to push in. When I got about half of my cock buried in her ass, I again paused and asked if she was okay. She said that she was better now and it just felt like her ass was full. I told her,

"I am only half way in"

and then I proceeded to push until the tip of my cock felt something that was probably the end of her rectum. I paused again and then slowly pulled out until the head was just inside her ass. I then slowly pushed back to where I felt something again. I then leaned so that my chest was against her back and said

"That wasn't fucking, that was just to let you get used to the feeling of having my cock in your ass. Are you ready for me to start fucking you now?"

She said to go ahead, so I slowly pulled out and pushed back in and slowly fucked her ass for about five minutes. I finally judged that she had experienced enough for her first session and pulled out. That drew a big sigh of relief from her.

I told her that I was intentionally going very slow and that she had not taken my entire cock into her ass this time. I told her that this time was more about getting her used to having my cock in your ass instead of fucking your pussy. I continued,

"That was nothing compared to the fucking that Jim will give me if you and Martha decide to push this on to the end."

She said that she understood and that it hadn't hurt as much as she feared. She added that she would reserve judgment on continuing until future sessions.

Second Session Four Days Later

This time, I went to her about an hour after dinner and told her to prepare to get her ass fucked again. I told her that I would not be using my fingers to loosen her asshole; I would simply lube her asshole and my cock and then start to fuck her. She would have to relax her asshole by herself if she didn't want it to hurt. I told her that I am still going to go slow, but there will be no stopping to allow her to adjust this time.

This time, she came out of the bathroom nude from the waist down. I made a point of lubing up my cock in front of her and then told her to resume her face down position on the bed. Once she was in place, I reminded her to spread her cheeks and used the extra lube on my hand to lube up her asshole.

I touched the tip of my cock to her asshole, saw it relax and pushed in until I felt something again. However, this time I pushed a bit harder until I was balls deep inside her ass. I had felt the tip of my cock get pushed to one side, so I suspect that my cock had started to turn the corner into her colon.

As I pushed this second time, she let out a faint cry. I stopped and asked if she was okay and wanted me to continue. She said that my final push had hurt, so I explained that she had just taken the entire length of my cock for the first time. I told her, because Jim's cock in longer than mine, taking Jim's cock in my ass would probably hurt me even more. Then I asked. Do you want to quit? She said no, so I pulled out and started fucking her by pulling almost all the way out and then pushing all the way in again.

I kept this up for a bit longer this time than I had the first time. When I finally pulled out, she said that after the pain at the end of my first push, that it didn't hurt like it had last time. She said,

"In fact, I was even starting to enjoy it, just a little bit. It feels much different from having you fuck my pussy"

So I told her

"And it feels very different for me because your asshole is much tighter and stronger than your pussy muscles. If I keep that up for very long and you were to squeeze hard on my cock with your asshole, you could end up feeling me cum in your ass."

Session 3 Three days Later

It is now one week down and seven to go.

I have been trying to keep her off balance by not knowing when I am going to tell her that I am going to fuck her ass. The first time, I waited for four days and fucked her after dinner, this time I only waited three days and told her an hour before lunchtime.

I found Sharon in the living room and told her to go prepare for an ass fucking. She got up and went into the bathroom. While she was cleaning herself out, I stripped from the waist down and lubed up my cock to be ready for her as soon as she came into the bedroom.

I told her to assume her position and did not have to remind her to spread her cheeks this week. I climbed up behind her, lubed up her asshole and immediately pushed my cock into her ass. I didn't pause until I felt the end of her rectum. I gave her a second and then plunged the rest of the way in. I waited a second and then started fucking her. This time, I didn't go as slow as I had been. This pace was about what I would give her pussy if I was trying to give her a tender, but erotic pussy fucking.

I fucked her constantly like this for about 10 minutes. Several times, I felt her tighten her asshole around my cock, which felt great. I hope that she was doing that for my benefit rather than as an instinctive reaction to having something as large as my cock in her ass.

When I was about finished, I left my cock deep in her ass and leaned over so that I could brush the hari from her neck and kiss her neck. When I did this, she seemed to relax and I felt her clench her asshole around my cock. This time, I knew that it was for my benefit and not something instinctive.

I finally pulled out of her and rolled off to one side. I asked her how she was doing and she said that she must be getting used to it because this time it had started to feel pleasant just shortly after I had started my fucking motion.

I didn't say anything, but I thought to myself that maybe my plan was starting to backfire. I loved Sharon and so I was trying to avoid causing her any pain, but maybe my tender approach was teaching her to enjoy getting her ass fucked. Oh well, that wouldn't be so bad. I have enjoyed having my cock up her ass, especially when she has started to clench her asshole around my cock while I am fucking her. To me, that almost feels like simultaneously getting tight hand job on my cock while also fucking my wife. It would feel great to be able to cum in her ass and know that she had squeezed me just to make me cum.

Session 4 Five Days Later

I waited until just after lunch today to tell Sharon to prepare for another ass fucking. She knew that I would be asking more often than once a week, but I don't think she was expecting to put her ass out for fucking this often.

I was ready when she came out of the bathroom and immediately got on the bed and grabbed her ass cheeks. I lubed her up and immediately went balls deep this time. That got a gasp out of her since before this I had always given her rectum a chance to adjust before pressing into her colon.

I then started rapidly fucking her. I was trying to use speed rather than force because I wanted to save the forceful fucking of her ass for later. I tried to go as fast as I could without driving into her too forcefully. About half way through, I felt her ass clench around my cock. This was almost too much for me because I was already going at the speed of a hand job that is intended to make me cum.

When she squeezed my cock, she almost made me cum right then. I wanted to save that sensation for a later fucking, so I eased up the pace a bit to allow my prostate to calm down a bit before resuming my previous rapid thrusting. I fucked her for at least 10 minutes and the rapid pace was beginning to tire me out. I finally buried my cock deep inside her ass, brushed the hair off the back of her neck and kissed her neck before I pulled out and rolled to one side.

This time, she rolled over toward me and gave me a hard kiss. I wasn't sure what to make of it until she said that the rapid fire fucking had been "stimulating" and that apparently she was getting used to having her ass fucked because it didn't hurt at all this time. So I made a mental note to myself, next time she needs to get fucked very hard.

Two Days Later - Update from Jim and Martha

We had lunch today with Jim and Martha.

After lunch Martha and Jim came to our apartment and said that she was starting to adjust, but it still hurt. It sounded the certainty that she had started out the experiment with was starting to waiver. As she said this, Jim was standing a bit behind her and had a bit of a grin on his face, but not enough for Sharon to notice. Sharon told Martha that she was starting to adjust too, which wiped the grin off of Jim's face. As they left, Jim called me out into the hall. After Martha had walked on, I told him I had been taking it easy on Sharon because I love her and don't want to hurt her too much, but that our next session was going to be ver forceful. He looked at me and said "good".

Session 5 Four Days after Session 4

This morning after breakfast I told Sharon that it was time for another ass fucking. She went into the bathroom to prepare while I got undressed and lubed up.

When she came out, she got into position on the bed. I lubed her up and immediately plunged balls deep into her ass. I then started fucking her as hard and deep as I could. I didn't worry about doing it fast. I wanted to use all my weight to drive my cock into her ass with as much force as I could. I didn't want to hurt her, but I did want to convey to her that I really didn't want to have to go through with this.