AUTHORS NOTE:

I decided to submit stories of my life’s anal encounters. Of all the women that I hooked up with over the years, fourteen of them included anal sex. Some of these were affairs that lasted for months and some for years. Others were memorable one night stands. Instead of going in chronological order I ranked the encounters according to the hottest ones beginning at number fourteen and working my way to number one. Over my lifetime dating back to 1959 when I turned 18 years old, I have had hundreds of sexual encounters with over fifty women. Being a leg and ass man, my most memorable encounters included anal sex. Most all of my sexual encounters were pleasant but these involved anal sex.

INTRODUCTION

My age will range from 29 to 48 during the years 1970 through 1990. The one thing that I pride myself on is staying fit through all those years and even today at age 72. I am 6’0″ tall and have always weighed between 205 and 215, my current weight. In the early years I played softball, football and basketball. Eventually I shifted to the individual sports of tennis and golf. I am still an avid downhill skier and SCUBA diver and I am still taking martial arts classes. In addition I make it to the gym at least three days a week and I am a ski instructor at a local ski area in the Midwest.

I love to travel and although not fluent, I am very comfortable with the Spanish, Italian, and French languages. I am also currently studying Mandarin Chinese. I enjoy reading and the arts and I am a frequent live theater attendee. I have traveled to Spain, Italy, France and the UK over the years as well as some of the best SCUBA diving spots in the Caribbean and best ski mountains in the U.S. and Europe. Some of my other story submissions to literotica speak to my experiences in other countries and islands as well as at home in the states. I served four years in the Marine Corps and I was honorably discharged in 1963.

I will begin the stories with number 14 and work my way up to number 1. Due to the length I have broken the stories up into chapters so that a single submission would not be too lengthy. Also there will be some redundancy in the description of sex acts, after all how could there not be. I had my favorite positions and activities and they were often repeated with different partners. The ranking and dates of the encounters are as follows:

1-Cathleen (1985 -1990) 2-Charlotte (1970-1972), 3-Bonnie (1974), 4-Pamela (1973), 5-Beverly (1977), 6-Sherry (1983), 7-Peggy (1976), 8-Lee (1982), 9-Barbara (1984), 10-Rita (1978), 11-Terri (1979), 12-Susan (1971), 13- Toni (1978), 14-Cindy (1973).

NUMBER 14 – CINDY

I met Cindy in 1973 at a college bar hangout in Cedar Rapids, Iowa. I was 32 years old at the time and still holding my own with the ladies. At 6’0″ my weight was holding at 200 pounds and I was in great shape. I still worked out all the time at home and on the road and I played softball for three teams at home.

Our manufacturing company headquartered in Ohio was relocating a division office from Illinois to Cedar Rapids, Iowa and I was assigned the responsibility of assuring that the computer systems were installed properly. The local sales representative for our computer vendor made sure that the equipment was delivered on time for the cutover. Randy was a nice guy in his thirties and we hit it off. He took me out for lunch several times on his company’s expense account. The day we went live with the new system he wanted to celebrate so he took me out for dinner and drinks.

After we ate randy took me to a bar where it was mostly people in their twenties who went there and many of them were college students. The bar was very diligent about checking identification so that everyone there was at least 21 years of age. Randy and I were comfortable talking with the girls there and holding our own with the younger guys. Disco was popular in 1973 and I was a pretty good dancer. I danced with a number of girls but there was one who seemed to pursue me.

Cindy was 23 years old and a cute brunette with long straight hair. I loved the way her hair flowed when we danced a hot disco number. I guessed her height to be about 5’5″ and her weight to be in the 110 to 120 range. She had a somewhat shapely figure but her waist wasn’t that small. Still she was firm and I could feel her hard abs when we danced. She had a cute ass outlined in her hip huggers and medium size breasts that I assumed were real. I tried to put the moves on her to get her to come back to my hotel with me but she shied away.

“I don’t know,” she said each time I asked her.

Thinking that I was going to strike out with her I turned my attention to another girl who seemed interested in me. I was dancing with this girl named Sharon when I saw Randy talking with Cindy. After a few dances with Sharon, I excused myself to use the men’s room. When I came out Cindy smiled at me and said, “My turn.”

“To use the men’s room,” I joked.

“Funny,” she said and made her way to the ladies room.

“I’ve been working on her for you,” Randy said.

“Really,” I quipped.

“Yeah, I’ve been telling her what a great lover you are. That you spent time in France and Italy and really know how to make a woman feel good. I told her that she would experience nothing like it,” he told me.

“That’s laying it on pretty thick,” I responded even though he was right. I had spent time in Italy and France when I was in the Marine Corps and those women taught me a lot about being a good lover.

“I think that she likes you but is still unsure. I told her that there is nothing like making it with an older more experienced guy,” Randy added.

“You make me sound old,” I laughed.

Just then Cindy rejoined us and pulled me out on the dance floor for a slow dance. I held her tight to me and I knew she could feel my stiff cock pressing into her thigh. “Have you given it anymore thought?” I asked her.

“Yes, but I still don’t know. I don’t know you and that makes me nervous,” she told me.

“Do you have any friends here?” I asked.

“Yes, a couple.”

“Why don’t you give them my name and the hotel where I am staying? I will give you my driver’s license so you can get the name and address from it,” I offered.

“I like that but I have my parent’s car and I need to get it back to them,” she shared.

“I’ll follow you to your parent’s house so you can drop off the car and then I’ll bring you to the hotel. I will bring you back home later,” I suggested.

“Okay, I’ll give Suzie your information and ask her to alibi for me. I’ll leave a note for my parents that I’m staying over at Suzie’s place,” Cindy explained.

The dance ended and I gave Cindy my driver’s license. I watched as she wrote down the information and chatted with her girlfriend. Suzie looked over at me several times and smiled as if she was giving her approval of Cindy’s choice in men that night. Cindy came back and gave me my license and then I told Randy I was taking off. He was talking with a full bodied girl and I sensed that he had had enough to drink that he just hoped for a blow job. He told me he would see me in the morning.

I got in my car and followed Cindy to her parent’s house. I knew she was serious about coming back with me because she made sure that she did not lose me. There were so many turns in the subdivision that she could have shaken my tail any time. I waited as she went in the house to drop off the car keys and leave her folks a note. Minutes later she was in my car giving me directions to get back to the main road. Once there I drove to the hotel and brought Cindy to my room. As much as I liked anal sex it was the furthest thing from my mind that night as I truly wanted to pleasure Cindy even though she had a cute ass.

The first thing I did was to undress her and I did it in front of the mirror in my room. I had Cindy face the mirror and I stood behind her. First I removed her blouse and I kissed her neck and tongued her ear as I unbuttoned it. She shivered and cooed in my arms and then I slid the blouse off her shoulders and down her arms. Looking at her in the mirror I could see that he breasts were indeed real. I unhooked her bra and slid the straps off her shoulders. I eased the straps down her arms and removed the bra letting it fall to the floor by her blouse.

Cindy’s hands instinctively covered her firm breasts but I pried them off as I continued to kiss her neck. She turned her face to me to be kissed and I pushed my tongue into her mouth. She responded by shoving her tongue in my mouth and we French kissed as I fondled her firm breasts. I felt her nipples harden in my palms and I tweaked them ever so gently. Cindy was moaning softly in my mouth. I let my hand drift down from her breasts along her flat belly and firm abs to the belt around her waist. I unbuckled the belt and then unfastened the buttons on her hip huggers.

I broke the kiss with Cindy and I dropped to my knees behind her. I removed her shoes first and then pulled the snug fitting hip huggers down her shapely legs. Being a leg and ass man, I admired Cindy’s legs and curvy ass. I removed the hip huggers on legs at a time as she lifted her leg to assist me. I tossed the slacks in the pile with her other clothes. Next I kiss the back of her thighs and she trembled as my lips grazed over her skin. I kissed my way up to her panty covered bottom and then slowly pulled her panties down her legs.

Cindy lifted one leg at a time as I removed her panties and there was the distinct smell of sex emanating from her pussy. I planted soft kisses on her buttocks and she surprised me when she pushed her ass back in my face. Suddenly I realized that anal sex may be a possibility that night but I did not rush it. I ran my hand up the inside of her leg and found her pussy to be sopping wet. I toyed with her vulva and fingered her briefly before standing back up. My cock was throbbing in my pants and it was time for me to undress. I removed all my clothes and then totally naked stepped behind Cindy again. I let her feel my hardness against her firm buttocks and she wiggled her ass in response.

I turned her toward me and knelt in front of her. I pressed my mouth to her vulva and her hands held my head as if she was afraid that I would stop. She was dripping wet with desire and I tongued her clit causing her to orgasm quickly. Cindy held my head tight to her pussy as she thrust it at me and cried out. “Oh Walt, hold me, hold me tight.”

I held her by the cheeks of her ass as she exploded in my mouth. Cindy trembled as held to my head for balance. Then her hands dropped to my shoulders for more support. I continued to lick her and tease her clit until she pushed my head away. “Oh I came so quickly. Let me lie down,” she pleaded.

I pulled the bed covers down and laid her on the bed. She looked radiant as she smiled and held her arms out to me. I moved between her legs as she lifted them out to the side and my rigid cock slid in easily. Cindy gasped as my cock filled her quim and she wrapped her legs around me and locked her ankles together. I was in no hurry to cum and I wanted to please her over and over before I finally did. I was still good for at least two ejaculations and I knew that the second one would take longer.

Cindy was turned on beyond belief and she was insatiable. She had two more orgasms and I still had not cum. The last orgasm was so intense that it scared me but she was used to having volcanic like climaxes. She needed to let her clit rest for a while so she moved to all fours and I fucked her from behind. It was my favorite position particularly if the girl had a nice ass and Cindy certainly did. I caressed her buttocks and teased her nether hole which was very tight. I was sure that she never had experienced anal sex. I wet my pinky finger with her pussy juice and eased it into her anus. Cindy stopped moving briefly and then resumed moving her ass around with my little finger in it.

“I have been thinking about anal sex but I am still afraid. Your cock is bigger than most too,” she whispered.

“If you want to try I’m game. We will need to use some cream to get you very slick. If at any time you feel scared or are worried, we can always stop,” I told her.

“I want to try it,” she agreed hesitantly.

I eased my cock out of her pussy and then knelt behind her. I lapped at her pussy gathering up some love juice and then I tongued her anus. I thought Cindy was going to leap off the bed when my tongue touched her nether hole. However she loved it and I continued with the anal foreplay. “You certainly know how to get a girl all hot and bothered,” she rasped.

“I’m going to get some lotion,” I told her as I moved off the bed.

I got the hotel supplied body lotion and used it to lubricate her anus, I had her pussy juice and my finger was very slick as it entered her rectum. I used my index finger to stretch her a little and then switched to my middle finger. After several minutes of using my fingers, I introduced my thumb to her ass and it was a snug fit. Still Cindy was determined to go through with it and did not protest. I felt she was ready for the real thing and I knelt behind her.

I applied and ample amount of lotion to my cock along with my saliva making it as slick as possible. I eased my cock into her ass and she grunted as the mushroom head cleared her sphincter. “Oh, oh, wait,” she cried out.

“Should I stop?”

“No, just stay still for a minute. Let me get used to it,” she whispered urgently.

I didn’t move with just the head of my cock in her ass. Several minutes passed and the n Cindy moved back a little and accepted more of my cock in her bottom. This continued for what seemed like and eternity and even then only about half of my cock was in her ass. That was enough for her though and she controlled the action. She moved her ass back and forth on my cock each time stopping when she felt full. I looked at her beautiful ass as my cock slid in and out and that was enough to get me to cum.

“Cindy, I’m going to cum. Do you want me to pull out?”

“No, I want to feel it. I want you to cum in my ass,’ she replied excitedly.

“Here it comes then,” I announced as I ejaculated in her rectum.

It was a good size load as my first always was and Cindy cried out when she felt the warm sperm flood her rectum. “Oh, oh, oh, yes, I can feel it,” she called out.

My cock stayed hard in her and I could feel he sphincter contracting and relaxing around my shaft. I waited for several minutes and then I eased my cock out of her ass and watched as my seed trickled out and ran over her pussy down her inner thighs. Cindy involuntarily contracted her sphincter and more semen oozed out of her anus. It was an incredible sight to see her cute round ass expunging semen. I caressed her buttocks until she flipped over.

“I feel like I have to poop,” she said.

“That’s natural after anal sex,” I told her and then offered, “Let’s shower together and get cleaned up.”

Cindy and I showered together and rinsed the semen from her body. I helped her douche her anus with the shower water and afterward we dried off and went back to bed. We cuddled together and caressed each other causing me to get hard again. Cindy saw my erection and slid down the bed to take it in her mouth. She sucked on my cock giving me a very good blow job.

“Turn around,” I encouraged her.

Cindy rotated around and straddled my face. I lifted my head to get my tongue on her clit. We stayed in the 69 position until I ejaculated in her mouth. Cindy swallowed every drop and let my cock soften in her mouth. She managed another orgasm and I tasted her juices. We eventually moved to a spoon position and I draped my arm over her body and cupped her breast.

“Can you take me home? I should get going,” she whispered.

“You’re welcome to stay her but if you want to leave now I’ll drive you home,” I told her.

“Yes, it will be better if I get home early,” she replied.

We got up and got dressed and I drove her back to her parent’s house. I paid close attention to all the street names and turns so that I could find my way back to the main drag. As we drove Cindy told me that she was glad that she tried anal sex but she wasn’t sure if she would do it again. Her bottom was still a little sore and she felt constipated. I told her that she would feel that way for a few days and then it would pass. I explained that the sphincter was stretched and it was designed to push things out not to take things in. She nodded that she understood.

I dropped Cindy off and we never exchanged contact information. I wasn’t sure if I would ever get back to Cedar Rapids anyway. I managed to find the main drag without getting lost and made my way back to the hotel. My flight home was scheduled for that morning but I changed it to an afternoon flight so I could sleep in. It was very easy those days to change flights without a hassle.

NUMBER 13 – TONI

I had changed jobs in 1976 and I was working for another manufacturing company located in Ohio. In 1978 I played on the IT team in the company intramural volley league. The teams were coed and we had to have at least two girls on the court at all times. One of our players Toni was a recent college graduate and an entry level programmer in our department. She was an attractive young woman but by no means a head turner. She was 6’0″ tall and weighed about 145 pounds. Toni had a very straight line figure with medium size breasts. The one thing she had that many tall girls don’t have was a nicely shaped ass.

Toni was conscious of her appearance at work and she always wore long loose fitting clothes. On the volleyball court it was different as she wore shorts and a tee shirt. That’s when I noticed her curvy ass. I had never even given a thought to having sex with Toni as I was currently seeing two other girls who did not work at the company. One evening after one of our games some of us joined Toni by her Volkswagen van for a beer. I had supplied the beer and the cooler was stored in Toni’s van.

After a couple of beers everyone else left leaving Toni and I alone with the beer. The bugs were getting to be a pest so she suggested we sit in her van and finish our beer. As it turned out we had a few more beers and I was starting to think about getting some pants that night. Toni leaned over her seat to fish two more beers out of the cooler and as she did she put her fine ass on display. I could not resist and I ran my hand over her firm butt.

“Nice,” I said.

“I’ll give you an hour to stop that,” she said slurring her words slightly with a giggle.

“Game on!” I thought to myself and I continued to fondle her shapely buttocks.

“Let’s get in back,” she said in a hurried raspy voice.

I suspected that she was horny and in the mood for sex. I climbed in back with her and we lay on the floor of the van. I took her in my arms and kissed her and she kissed me back. Next our hands were fumbling with the other’s clothing and I had her tee and bra pushed up baring her cute firm titties. I mouthed them and sucked gently on her nipples as I slipped one hand between her legs and rubbed her snatch through the shorts. I kept my mouth fastened to her tits as I pushed her shorts and panties down below her pussy. I fingered her quim and found it soaking wet with desire.

“Shit, shit, oh shit,” Toni whispered as I worked on her.

I removed my mouth and moved down so I could remove her shorts and panties. Now she was nude except for the tee and bra pushed up above her tits. I moved between her legs and licked across her vulva causing her to thrust her cunt in my face. She continued to utter the word shit over and over as she approached her first orgasm. When I slipped my fingers in and located her g-spot that did it. Between rubbing the g-spot and nibbling on her clit she went wild. Toni juiced my face as her body seemed to go into convulsions. I kept at her and did not let her escape until she was finished cumming and her body went limp.