tagMatureHow Many Times Can 66 Go Into 38?

How Many Times Can 66 Go Into 38?



This story is completely fiction but it based on some past affairs, some fantasies and a recent event. It touches on some infidelity, vaginal, oral and anal sex. If that is not to your liking I suggest that you not read the story. As always your feedback and comments are welcome.


I had been married for almost 45 years when I lost my wife to cancer two years ago. In the middle years of my marriage I traveled a lot on business and had my share of extra-marital affairs. I never knew if my wife suspected but if she did she chose to ignore it and we stayed in our marriage. For the last twenty years of our marriage I had remained faithful and I had reconciled with my faith. During the years of unfaithfulness I became a big fan of anal sex. My wife was never interested in anal sex or being on the giving end of oral sex but that was very available outside the marriage.

After I retired from the business world we decided to move closer to my daughter's family and four grandchildren. We built a house on a two acre wooded lot in the Midwest as we enjoyed the four seasons and wildlife. Our property was very private as it was surrounded by trees and backed up to wetlands. The house was bigger than we needed but it was designed so that we would live on the first level and the lower walkout level was for entertaining and the grandchildren. The lower level had three bedrooms, a game room, TV room, exercise area, a full bath and a library. There were also two patios on the lower level.

After my wife passed away I decided to keep the house since the real estate resale market was very soft. Whenever I did decide to move I would also have an estate sale since we had so much furniture, art work and collectibles.

I have always been one to take care of my body and at age 66 I was very proud of my fitness and stamina. I was an avid skier and a year ago I joined the Ski Patrol and worked a couple of days a week at a nearby ski area. I worked out all the time and I was at the gym at least three days a week and sometimes I made it six days. I still SCUBA and I belong to a dive club. I also am in a martial arts black belt program.

For the past two years I have not sought out any female companionship. I always said that I would never marry again and I still have no desire to remarry. I socialize a lot with friends but I don't date. I had always been active sexually and for the past two years I have found enjoyment with some quality porn. I have a decent DVD collection of movies from the company Private Label. The European women are beautiful with natural bodies and they all seem to take a cock in every hole. I have no trouble getting an erection and getting off to these quality movies. Up to now I haven't had the need for an erectile dysfunction drug as the porn works for me.


Barbara is one of the many women I met while working out at the gym. Even though I have my own exercise equipment, I prefer the socializing at the gym while I workout. I also like to watch the ladies work out. I love watching their fit bodies covered with tight pants or barely covered with loose fitting shorts. I don't stare at them but I glance at them enough to check them out. Being a leg and ass man the gym is a great place to check out the ladies. Of course many of them are married and have children in the daycare but the way they dress they draw attention to themselves.

I first noticed Barbara on the tread mill one day and I thought I was seeing a ghost. She looked so much like my secretary of eight years Cathleen that it was scary. Cathleen was my secretary in the 1980's who I had an affair with for six of those eight years. She was my last act of infidelity. Barbara looked now like Cathleen did back then. She was 5'6" looked to weigh about 125 with short blonde hair. She had small breasts and a shapely ass just like Cathleen had.

During our affair Cathleen and I had sex in the office at least three times a week. We also went to a romantic interlude hotel once a week. In the office it was always oral sex but in the hotel I got to fuck Cathleen's sweet hot ass. She loved it in the ass and I loved giving it to her. I also took good care of her pussy. So as I watched Barbara on the tread mill I reminisced about Cathleen and visualized my cock sliding into her curvy shapely ass. I realized that I was getting a hard-on and that I had been staring too long at Barbara.

I moved on to finish my workout but I made a pledge to meet Barbara before I left the gym that day. Meeting her was pretty easy as everyone was very friendly at the gym and talked to one another all the time. When she finished her tread mill session, Barbara headed for the machines. As she spotted me our eyes made contact and we smiled at each other. We both continued with our exercises and then Barbara had trouble with on of the settings on the leg extension machine. I loosened it for her and helped her with the setting and then introduced myself.

"Hi I'm Walt," I said as I stuck out my hand.

"Barbara, but call me Barb," she replied as she took my hand and then added, "Thanks for your help."

"Anytime," I told her with a smile.

"You're here a lot, well at least every time I'm here," she continued the meet and greet.

"I try to stay in shape. It gets harder the older you become to stay fit," I replied.

"Well you look good. How old are you?" she inquired.

"I'm 66 heading for 67 this summer," I answered proudly.

"You're kidding 66, you look great. What ever you're doing keep it up it's working," she complimented me.

"I probably should let you get back to your workout," I suggested.

"Yeah I should finish up and get back to the office, although the real estate business is slow these days," she replied.

"I guess it is especially with all these foreclosures and bankruptcies," I added.

"That hasn't hit us here like in other parts of the country but the resale market is still sluggish. I have some builders I'm working with and I am trying to focus on moving new properties," she told me.

"Well good luck with that, I'll leave you alone now. I already took a lot of your time," I offered.

"Well it was nice meeting you and I'm sure I'll see you here again," she said with a smile.

We both resumed our workouts and I glance at her several times as she went through her workout. She focused on her legs, abs and ass. Her ass really looked great when she did the leg curls as her butt muscles tightened with each leg curl. I already knew that I would be thinking about Barbara with my cock in my hand as I watched one of my favorite porn flicks.

I finished my workout long after Barb left the gym and I showered and dressed. I decided to stop in the local café for a latte and read the morning paper. I was sitting in one of the easy chairs in front of the fireplace with my feet on the ottoman drinking my latte and reading the paper when I heard a familiar voice.

"Small world mind if I join you?"

I looked up and saw Barb standing there with a coffee in her hand. "No not at all, please do I would love some company," I invited her to join me.

Barb sat down in the other easy chair and shared the ottoman with me. I offered her part of the newspaper but she graciously declined.

"I thought that you may want to look at the real estate section," I teased.

"Funny," she laughed.

I put the paper down and then we chatted for quite awhile. She was very easy to talk to and we got along very well. Barb was younger than my daughter by a couple of years but she was comfortable conversing with me. She learned about my wife passing, my daughter's family and my current set up with my house. When I described the house and told her about the three season room with a hot tub she loved it. Barb told me about her failed marriage and her reluctance to get involved again. She did date occasionally but she hated the bar scene.

"That's the one thing I do miss at our gym, no Jacuzzi, sauna or steam room," she sighed.

"Well if you ever want to use the hot tub at the house, you are more than welcome," I offered and then immediately regretted it.

"I'm sorry I did mean that in a neighborly way not as a come on," I apologized.

"I knew how you meant it and that's very nice of you to offer," she replied sincerely.

We talked some more and then she learned that I was a Ski Patrol at the nearby ski area. Barb shared with me that she had always wanted to learn to ski. I told her that there were some good instructors at the resort and I added that I could always teach her if she wanted to try. She actually got excited about the possibility of learning to ski. I told her about my friends in Chicago and how we met up every year in Colorado for two weeks of skiing. Barb confessed that we would love to ski in Colorado someday. We finished our coffee and then exchanged phone numbers before we said goodbye and went our separate ways.

That evening I reflected on my earlier affair with my secretary Cathleen as the image of Barbara was etched in my mind. I thought back to one of our sessions in the romantic interlude hotel. I recalled every moment as if it were yesterday.

The first time we went to The Chateau was memorable. We entered the room and wasted no time taking off our clothes as the Jacuzzi filled with hot water and bath gel. Cathleen and I showered together before entering the Jacuzzi. We soaped each other up and played with each other's bodies being careful we didn't cum in the shower. Cathleen then would douche both her pussy and her asshole. It was the first time I had ever seen a woman do that and it was kind of erotic.

After showering we entered the Jacuzzi armed with a bottle of wine. I turned on the jets and we kicked back enjoying the bubbles and our first glass of wine. After awhile Cathleen leaned back into me and I reached around and stroked her cute titties tweaking and rolling her nipples in my fingers. I slid one of my hands down across her firm abs over her little blond tuft of hair and found her vagina. I played with the folds of her labia and then inserted my fingers in her pussy. I found her hard clit and rolled it between my fingers as I continued to tease her nipples with my other hand.

As Cathleen got turned on I moved her to the other side of the Jacuzzi and had her lean over the edge presenting her shapely ass to me. Her ass always looked good but this it glistened with water and bath gel and looked so sensual. I leaned over and licked Cathleen's pussy from behind driving her wild. Then I had the urge to tongue her beautiful ass so I swiped my tongue from her pussy up and over her bung hole and back to her pussy. She gasped out loud when my tongue touched her asshole. I really got into it and grasped both of her curvy ass cheeks and pulled them slightly apart so that I could get my tongue in deeper. I probed her pink aperture with my tongue as I inserted three fingers in her pussy. She started whimpering, gasping and directing the action.

"Oh my God, do it again. Lick my asshole; stick your tongue in there. Eat my pussy, tongue my ass, rim me, oh yessssss," she cried out.

I grabbed the bottle of wine and poured some in the crack of her ass letting it trickle down over her anus and pussy. I placed my mouth on her and drank up the wine swabbing her pussy and ass in the process. I repeated this several more times until Cathleen seemed to go into convulsions with her first orgasm of the evening. She collapsed back into my arms and I stroked her smallish tits as she recovered from the intensity of her orgasm.

"Not in my wildest dreams did I ever think that someone would stick a tongue in my ass, nor did I know it would feel so wonderful," she uttered in an exhaustive voice.

"I surprised myself by going after your ass. I have never done that before but it just looked sexy as it glistened with water. Of course I remembered that you had douched and it looked so clean. I think I have found a new way to drink wine," I replied.

We decided to get out of the Jacuzzi before we turned into prunes. We dried off and flopped down on the water bed. Cathleen began to stroke my cock into an erect state and then proceeded to suck on it. She loved to stick her tongue in the little hole and nibble on my cock head. This always made her hot and she needed my cock in her pussy. She straddled me and aimed my cock in her hole and rode me until she achieved another orgasm.

It was time for me to fuck her in the ass so I had her kneel on all fours with her gorgeous ass in the air. She always put her head on the mattress and turned to the side so that she could watch. This time she had the added benefit of mirrors on the wall and ceiling and so could clearly see the penetration. I broke out the lube and put an ample amount in her asshole. I fingered her ass and pussy at the same time.

"I love the feel of your fingers in my ass and pussy together," Cathleen exclaimed!

If there was one thing I liked besides fucking a beautiful ass is preparing an asshole for a good reaming. After several minutes of finger fucking her pussy and asshole I couldn't wait any longer and I had to get my cock in her beautiful ass. I removed my fingers and lined up the head of my cock at her moist puckered ring and pressed forward slowly. My cock head strained to pop through and she let out a little groan as the pressure from my iron hard dick forced her little ring to open like a flower and suddenly my large mushroom head slipped past the ring and into her ass. Cathleen let out a groan as her rear passage was stretched to accommodate my ample girth.

"Oh you are going to make me like this more than the regular way," she gasped and shivered as I filled her fully and withdrew my penis slightly.

I felt her ass tighten around me and I continued to slowly stroke in and out of her tight ass until all 7+ inches were tightly packed up her ass. Cathleen really began to moan and her whole body shook in anticipation of what she knew was coming. I began to slowly fuck her but soon picked up the pace as I penetrated her with long hard strokes that used the entire length of my thick cock. Cathleen was going wild as she loved the feel of my cock as it pulled out and then came crashing back in as my big heavy balls bounced off her clit. Cathleen was thrashing around uncontrollably, gasping and moaning with pleasure. When I reached underneath her to stroke her clit she exploded with her third orgasm of the night.

I continued to hammer her ass with long strokes then suddenly I felt that familiar tension in my balls and I knew I was close. I began to piston my raging cock harder into her searing ass in search for my release, which also increased the intensity of her orgasm. She was yelling and moaning, clawing and scratching at the cover of the waterbed begging me to cum.

"Give it to me, give it to me, give me your cum, cum in my ass," she begged.

I felt powerful and dominant with my impressive dick stuffed up the beautiful ass of a woman who could not get enough of me. Cathleen lay submissively before me on all fours as I towered above her like some untamed animal with a strong sexual hold on her. I took firm hold of her hips and slammed once more full force into Cathleen's ass. I did that three or four more times and then I let out a loud groan as I emptied my seed deep into her bowels. I couldn't believe how much cum I produced as my dick continued to hammer into her ass.

When I was finished I pulled out of her ass as Cathleen collapsed on the bed utterly spent. I slumped down next to her quivering body. I looked over at Cathleen and I noticed my seed oozing from her asshole. It resembled a natural spring as the jizm just seemed to bubble up as she tried to relax her spasming anal muscles.

Cathleen and I got up, showered and returned to the Jacuzzi where we soaked our aching muscles. After the Jacuzzi I offered her a massage which she gladly accepted. I had her lay face down and worked her back, legs and buttocks. Not so surprisingly I got an erection as I massaged and fingered her ass again. Very surprisingly I came a second time that night when I fucked her ass again. After the ass fuck I rolled Cathleen over on her back and continued the massage this time working her tits, abs, legs and pubes. I finished her off with another thorough pussy eating which had her screaming my name and humping my face with her volcanic orgasm.

I was brought back to reality when my cock erupted in my hand and cum landed on my pubes. That was one of my better cum shots in recent years as I was very turned on by thinking it was Barbara and not Cathleen that I was fucking.


Several days went by and I saw Barb at the gym more frequently. One day she approached me and asked if the offer to teach her to ski was still open. I told her anytime since my schedule was very flexible but that the best time was on a weekday in the early afternoon. So we made a date to go skiing the following Tuesday. I got her address and told her I would pick her up about 10:00 AM. It was a little less than a two hour drive to the ski area.

The following Tuesday I picked Barb up at her place and we drove up to the ski area. I suspected that she wouldn't have all the right gear so I packed some things just in case. She was thankful for the neck gator and goggles. I got her fitted for the right rental equipment and she got the best available since all the guys knew me. We started off on the bunny hill of course and then quickly moved to the beginner chair lift. Barb was a quick study and her fitness paid off. We skied for a couple of hours and then took a hot chocolate break. After the break I took her to another area and she progressed very quickly. She fell in love with skiing and she was now determined to buy her own gear. I told her to wait until the end of the season when the prices were slashed and I would help her pick out her skis.

After another hour, Barb was exhausted so we quit for the day. We stopped back at the lodge and I got her a hot chocolate with a shot of Baileys in it. She sipped it and loved it. We relaxed for awhile with a second drink and then decided to head home. Barb was sore as predictable but not as sore as she would be the next day. I told her that she used muscles that normally don't get used and that tomorrow she would feel it in her shoulders and her calves. As we drove home Barb fell asleep in the car and didn't wake up until we were about five miles from home.

"Sorry I wasn't much company was I," she said and yawned.

"Don't worry about it I had the music to keep me company," I replied.

"Is that offer to use the hot tub still open? Every muscle in my body aches," she asked.

"Sure and I have plenty of bathing suits so I'm sure that you can find one that fits. One of my daughter's should actually fit you pretty well," I offered.

"Great then we don't have to stop at my place then," she sighed as she rested her head back on the seat.

We arrived at my house and I pulled right in the garage. Barb followed me into the house and I got her a bathing suit and showed her to the guest bedroom and bathroom on the first floor. I then changed into my bathing suit and grabbed a couple of terry robes for us. I opened up the hot tub and turned on the jets. Then I opened a bottle of wine and brought it into the three season room. Barb entered the room shortly after and stepped into the hot tub. I told her to lie down in the lounge section and she sighed deeply as the jets soothed her body.

"Whoever said that there is no heaven? I bet that God has a hot tub up there," she said as she completely relaxed in the water.

I poured the wine in the special plastic wine glasses that I used for the three season room. I handed a glass to Barb and she smiled as she accepted it. She sipped it and told me how good it was.

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bywalterio© 6 comments/ 122068 views/ 22 favorites

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