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 8 — LEE

It was 1982 and I was working with a software company in Chicago. I was the Regional Manager and I was helping out the staff with sales calls and qualifying prospects. I received a call from my District Manager in Dallas and he asked if his new tech support person could shadow me for a few days. He felt she would learn more from me visiting prospects than just reading manuals. I agreed and a pretty blonde young woman named Lee was on her way to Chicago.

I met Lee at O’Hare airport and we called on a few prospects in the north suburbs. Afterward I gave her a brief driving tour of Chicago and then we stopped for dinner in the hotel restaurant where she was staying. During dinner Lee seemed to feel the effects of the wine.

“I shouldn’t drink so much wine. It always makes me feel romantic,” she whispered across the table.

I just smiled at her and then looked at her in a different light. I felt that she was there for the taking. Now I studied her features closely. She had long blonde hair that came down past her shoulders. Her eyes were very blue. Lee was 5’11” and even taller when she wore heels. Tonight she had worn a blue dress that had a slit in the side and every once in awhile her shapely leg would appear. She had nice sized breasts and she was very fit. After dinner we went to her room and I asked if I could join her for an after dinner drink in her room.

She snuggled in close wrapping her arm in mine and whispered, “I’d love that.”

Once in the room we kissed and then peeled the clothes off one another. Lee got in the bed and lay back as I took in her beauty. For a 33 year woman she was in great shape. She had nice legs, a narrow waist, great abs and nice tits. I looked at her pubes and noticed the light blonde tuft of hair above her pussy.

I walked over to the bed and sat on the side of it. I stroked Lee’s shapely legs and luscious thighs. My hand drifted up to her mound and I felt that she was wet with desire. She smiled at me as I fingered her pussy and licked my fingers clean of her juices. Then she opened her arms and welcomed me into her body for the first time. I slipped between her thighs and slid my hard cock into her quim. Lee uttered an audible gasp as I hit bottom. I began to fuck her slowly and eased my cock almost all the way out of her pussy before plunging it back in. She was lost in the lust of the moment.

“Oh that’s it fuck me, fuck me slow,” she whispered.

Just hearing her asking me to fuck her was an incredible turn-on for me and I picked up my pace. Lee threw her hips up at me as if to try and get me deeper in her cunt. I felt my orgasm approaching but I didn’t want to cum before she did so I tried to slow down.

“No, no don’t stop, fuck me faster, I’m so close,” Lee begged.

I picked up the pace again as we both raced toward our orgasms. I don’t know who came first because we were so close but Lee wrapped her long legs around me and humped me for all she was worth as I spurted my seed deep in her womb. We continued to fuck each other until we were drained. I collapsed on top of Lee and she didn’t seem to mind my weight as she held me and cried out.

“Oh thank you, I was hoping we would do this,” she said.

I rolled off of Lee and lay next to her on the bed. She smiled at me and then snuggled in closer. We talked for the next several minutes and she told me that she was happy that we got together. She told me that she was drawn to me because I didn’t hit on her before. As I lay next to her I caressed her breasts, neck and arms, teasing her skin with my fingernails and tongue. Lee made a low, drawn out sound. Deciding that I’d teased her enough I started on her naked breasts. As I sucked her warm flesh into my mouth and rolled a nipple between my teeth, Lee let out a moan of pleasure.

Lee then moved down the bed, gently took hold of my cock and took me into her mouth, rolling my cock around and getting it wet with her saliva, while her hand worked my shaft up and down at the same time. Seconds later, she straddled me. Her hand wrapped around my now slippery cock and I felt the tickle of her pubic hair just before her soft flesh nudged my helmet and then it was suddenly engulfed by the heat and tightness of her pussy.

Lee grabbed hold of the top of the head board on either side of my head as I held onto her hips. She rocked her hips back and forth, pressing downwards and working the walls of her pussy as I slid into her further. The next motion of her hips caused her to gasp in pleasure as my full length penetrated her. She began to work up and down, back and forth as she moaned in pleasure. She felt particularly tight in this position and the unhurried pace felt sensuous and wonderful. Lee continued to ride me at a slow, even pace as I relaxed and let her take charge. As she fucked herself on me I could hear the smacking and sucking sound of her pussy as my cock moved around inside her.

Her firm medium sized breasts jiggled as Lee picked up the pace. She pushed her hips down until our groins met and then lifted up until just the swollen tip of my cock remained inside her. She seemed to know just how far to move so that my cock never slipped out of her pussy. Her thigh muscles felt firm and tight under my hands as she worked her body on me. The speed of our groins slapping together increased as we fucked faster and harder. We really had our rhythm going now and I thrust up into her as she lowered herself on me. Her pussy contracted around my cock as her eyes fluttered and she emitted a high pitch scream. Lee grabbed onto my shoulders as she rode out her orgasm. I ejaculated into her again flooding her cunt with spunk as she collapsed on top of me.

Lee covered my face with kisses and then plunged her tongue into my mouth. As she kissed me she murmured softly into my neck and shoulders. She thanked me over and over as she held herself tightly to me.

“Oh my, I haven’t cum like that in a while,” she sighed and then added, “But I haven’t been fucked like that for some time and you came so much.”

As I lay by her side I noticed that her tits were standing straight up and her aroused nipples were pointing at the ceiling. I tweaked the hard little nubs between my fingers causing her to gasp and quiver.

“My breasts are very sensitive,” she murmured.

I leaned over and kissed her breasts and sucked on her sensitive nipples. I rubbed her firm flat tummy as I sucked on her tits and her rock hard nubs. I was still hard and ready to fuck some more.

“Oh I love that it makes me feel so feminine,” she cooed.

As I sucked her tits and continued to rub her belly, I let my hand drift down to her wet pussy. I ran my fingers through her soaked pubic hair. Lee begged me to let her rest as she was sure that she could not possibly cum again. I rolled her onto her stomach and lifted her hips to a level with my cock as I knelt behind her. I eased my cock into her pussy and began to fuck her doggy style. Lee was content in this position since I was not in contact with her clit. I slammed into her from behind causing her curvy ass cheeks to jiggle. As I fucked her from behind I looked at her tight asshole and wondered if anyone or anything had ever been in there.

I scooped up gobs of her pussy juice and smeared it in the crack of her ass spreading around her nether hole. I added saliva to my finger and probed her tight aperture with the tip of my finger. She tensed when she felt my finger probe her asshole. I gathered up more juices and added more saliva as I continued to probe her hole and open her up. I gently pushed a very well lubricated finger into her ass and the tiny aperture opened up to accept the digit. More saliva and more juices greased her asshole sufficiently to allow me to slide my finger all the way into her rectum.

Lee knew that I was preparing her ass for my cock when she said, “Please be gentle if you fuck my ass.”

“Don’t worry,” I assured her.

I eased my cock into her ass and I heard her gasp as I penetrated her. She quickly adjusted to my cock and I soon had a smooth rhythm going. I loved watching my cock slide in and out of her shapely ass as I caressed her lovely buttocks. Now with my in her ass I was approaching another orgasm. I could it build in my balls, travel through my scrotum and splash the insides of her rectum with my warm semen. I flooded her beautiful ass and then pressed forward leaving my cock in her. I stayed in position behind her as she milked my cock with her sphincter. I waited until my cock softened and slipped from her ass before I moved away.

Lee flopped forward on the bed and let out a big sigh. I took a quick shower, dressed and headed home. I reminded her that I would pick her up in the morning. Our plans were to go to the office first and then make some afternoon calls. In the morning Lee was in the mood to fuck again so I went to her room, undressed and got in bed with her. We had sex for hours with me finishing up in her magnificent ass. We showered and as we did I fucked her in the ass again. Afterward we dressed and stopped for a light late breakfast.

We started out at the office and then we made some more calls together. Lee had a late flight back to Dallas that evening and I dropped her off at the airport after dinner. I never did hook up with Lee again but it had been a wonderful experience just that once.

NUMBER 7 — PEGGY

I met Peggy in 1976 when I went to work for a small family held company. Working for a family run company was a mistake but meeting Peggy had its rewards. I only stayed with the family run business for three months and then I accepted a position running a data center for a large computer company. In the three months I was at the small company, I had a memorable affair with Peggy my boss’s secretary.

I first met Peggy when she greeted me in the reception area on the day of my first interview. When she walked in I thought that she looked like a very sexy young woman. She was wearing a light pink shear blouse with tight white slacks. Peggy was small breasted, almost flat chested but she had solid looking legs. She looked to be about 5’5″ tall and couldn’t have weighed more than 110 pounds. She had long brown hair and dark brown bedroom eyes.

She smiled at me and spoke softly, “Are you Walt?”

“Yes I am,” I answered.

“Hi, I’m Peggy. Please follow me,” she said and then she turned to lead me to the Controller’s office.

I thought about the old cliché, “I’d follow you anywhere,” as I walked behind her. I noticed that the back of the blouse was totally see-through and that she was not wearing a bra. Then my eyes drifted down to her fabulous ass framed in her tight white slacks. She was definitely one hot young woman. When we got to the Controller’s office I checked out the front of her blouse. There was enough of a pattern on the blouse so that it was difficult to see her small tits through the material. However the darkness of her nipples did contrast with the pink blouse.

I accepted the position days later and I was already thinking about Peggy and if she was available. I befriended a colleague named Frank at the office and he was dating a girl named Judy who happened to be a good friend of Peggy’s. One Friday, Frank came in and told me that Peggy’s date bailed out on her and he asked if I would be interested in going out with the three of them. I jumped at the chance to be with Peggy even though I knew it was somewhat risky since she was my boss’s secretary. I picked Peggy up at her place and then drove over to Frank’s house; we left my car there and Frank drove. That night the four of us then went out for dinner. Peggy wore a very tight mini skirt that showed off her shapely legs and curvy ass.

After dinner we went to this dance club where they had a good DJ. We grabbed a table, got some drinks and danced to songs that we liked. Peggy loved to dance and during the fast songs she really got into it. On a few occasions she moved her body in such a way that it caused her skirt to ride up and her panty covered crotch peeked out.

The evening was moving fast and we were having a lot of fun. As it got later we danced to a couple of slow songs before we called it a night. As I was dancing with Peggy she moved her hips side to side across mine. She was a very sexy dancer and I soon had a very noticeable erection. Peggy pressed her loins into mine and smiled at me.

“I can see that you enjoy dancing with me,” she whispered in my ear as she ran her hand over my crotch.

“Yes I do and you seem to bring out the best in me,” I whispered back and then tongued her ear.

I felt Peggy shiver slightly as my tongue dipped in her ear and then she whispered to me again, “But the best is not out yet, maybe later,” she teased.

I looked over at Frank and Judy dancing and they were locked in an embrace and a deep kiss. I turned my attention back to Peggy and then kissed her. She returned my kiss enthusiastically and plunged her tongue deep in my mouth. The four of us continued to dance as long as slow songs were playing. When the DJ returned to the faster songs we decided to leave and go back to Frank’s house.

Frank was driving and Judy sat close to him in the front. Peggy cuddled up to me in the back seat as Frank headed for his house. Peggy and I began to kiss in the back seat and I ran my hands over her upper body. I massaged her firm little tits through her blouse and she gasped in my mouth. Peggy then turned toward me, sat sideways and draped her legs over mine. Her skirt rode up and I could see the white crotch of her panty. I ran my hands over her legs and touched the bare skin above her hose. She trembled slightly but held me tighter and whispered to me.

“Take my panties off and play with my pussy,” she told me.

I was surprised by her request but I knew that I heard her correctly. When she said pussy it really sounded so damn sexy. I moved my hands up under her skirt and grasped the panty waistband. As I tugged them down her shapely legs Peggy lifted her hips slightly. I peeled them all the way down and off her legs. Before I fingered her pussy I just had to feel her firm ass. I reached under her and grabbed both of her firm round ass cheeks in both hands and molded them with my fingers. My cock was straining and was ready to burst through my pants.

“You like my ass, don’t you?” she whispered.

I whispered back, “I love your ass!”

I released Peggy’s curvy ass and slid one hand between her legs. I touched her pussy and I found it to be sopping wet. My finger entered her easily and she emitted a slight gasp at the penetration. I worked a second finger in her pussy and stroked them in and out. Peggy was going wild and she was breathing deeply into my mouth as we kissed. I let my middle finger slip out of her pussy and touch her anus. Peggy stiffened in my arms and then wiggled her ass as if she was giving me permission to explore her ass.

I pushed my moistened middle finger in her asshole and then located her clit with my thumb. I wiggled my finger in her ass and pressed my thumb against her clit. Peggy was bucking her hips slowly against my hand and kissing me deeply. I thought that she might cum any minute but at that moment the car pulled into Frank’s driveway.

“Okay everyone we’re home now,” Frank announced.

I looked up front just in time to see Judy sit up straight. Apparently she had been playing with and sucking Frank’s cock during the ride home. Peggy swung her legs around to sit straight and she adjusted her mini skirt. I handed her panties to her and she quickly put them in her purse. Up front Frank was obviously pulling up his zipper and fixing his trousers after he parked the car.

“Who is up for a nightcap?” Frank offered.

We all went in the house and gathered in the family room. Frank brought in some cordials and the four of us had a nightcap. It wasn’t long before Frank and Judy were necking again but this time they excused themselves quickly and headed up to Frank’s bedroom. Peggy was nervous about being in the house with Frank and Judy being right upstairs so I offered to take her to my place. Peggy smiled and told me she would love to see it.

We drove to my place and in what seemed like seconds Peggy and I were naked in my bed. Peggy then lay on her back, splayed her legs and pulled back the folds of her vagina.

“Here eat my pussy, please eat my pussy,” she pleaded.

I rolled over and got between her legs. I put her thighs on my shoulders and lowered my mouth to her pussy. I took one slow lick as I flattened my tongue on Peggy’s mound. It felt so smooth and warm and I knew I had achieved the desired effect from her moan I know that Peggy enjoyed it. I enjoyed the taste of her and I kept licking and eating her. I pointed my tongue and burrowed into her pussy as it parted her labia my tongue was rewarded with the exquisite taste of her juice.

Peggy was obviously enjoying what I was doing as she reached down with both hands and spread herself wide making it so much easier for my tongue to explore her pussy. My tongue explored all of her as my mind took notes of what seemed to turn her on. Peggy was breathing rapidly and she moaned softly whenever I got near her hard pearl. As I searched out her hard clit still just barely hidden she tensed and began to quiver. After I felt like I had teased her opening as much as I could with my tongue it was time to see her reaction when my tongue finally touched her sensitive clit.