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 3 – BONNIE

Bonnie and I had been out several times and we did sleep together each time. She was a great lay with a fantastic body but she had this odd behavior. She always acted reluctant toward anal and oral sex. When I came in her mouth she acted annoyed and when I fucked her ass she acted as if she didn’t want to do it, but she always did it and she never once refused to suck my cock or take it in the ass. I suspected it was her way of justifying her behavior.

I met Bonnie in night school in 1975. Bonnie was a vibrant young woman with light brown hair that just covered her neck. She had a nice figure with tits that I guessed to be a 34 C but her best feature was her round shapely bubble butt. I had always been a leg and ass man, so nice tits were a bonus but not a necessity, as I favored women with shapely bottoms. She looked great totally naked and I would often stroke and play with her fabulous body until she begged me to take her to bed. Bonnie had one of the nicest asses that I had ever seen and I loved fucking her hot ass.

One Friday night she invited me over to her place. We sat on the sofa watching TV, sipping our drinks and discussing the college class. I got up to refresh my drink and when I returned I sat next to her. She turned toward me and smiled nervously as she anticipated my next move. I smiled back and put my arm around her and drew her to me. I gently pulled her toward me and our mouths locked in a kiss. I pushed my tongue into her mouth and it took her breath away. Bonnie kissed me back and her body relaxed as she welcomed the fact that she would get fucked that night. I lifted her sweater up over her head as she held her arms up for me to remove it. Next I unfastened her bra and as I removed it her tits stood straight out from her chest. I pushed her shoulders back against the sofa causing her tits to look bigger and firmer. Bonnie moaned as I leaned over and kissed her breasts and sucked on her rock hard nipples. I kissed and sucked her tits for several minutes. Her nipples got so long and so hard that they were like little dicks sticking out from her tits. She loved to have her tits fondled and kissed.

I moved off the sofa and knelt between her legs. I unzipped her skirt and she lifted her hips as I pulled it down and off her body. Bonnie looked very sexy clad only in her thigh high nylons and her robin blue panties with her aroused tits standing straight out. Hooking my fingers in the waistband of her panties I slowly peeled them down her legs. As I removed her panties I stared directly at her snatch and gently pushed her legs apart. Bonnie groaned as I ran my finger over her well trimmed pussy mound and tickled her labia. Her hips jerked involuntarily when I probed her sopping wet pussy with my finger and kissed her inner thighs. Bonnie gasped aloud when my tongue finally touched her quim.

I raised Bonnie’s legs up and placed them on my shoulders which brought her pussy even closer to my mouth. Then I reached up and fondled her tits with both hands, tweaked her nipples and plunged my tongue into the depths of her pussy. I licked her cunt and located her erect clit with my tongue. As I sucked on her clit and played her tits and nipples, Bonnie moaned loudly as her body thrashed around. I struggled to keep my mouth glued to her pussy as her body jumped all over the sofa. Bonnie grabbed my head with both hands and held me to her gushing pussy.

“Oh Walt, this is going to be a quick one, a big one,” she cried out and then she screamed, “I’m cumming, oh God I’m cumming, hold me, hold me tight, please hold me.”

Bonnie’s body seemed to go through convulsions as her orgasm rocked her and sent tremors through her. She continued to hold my head to her mound as her sweet nectar gushed into my mouth. I licked her dry and nibbled on her clit which caused her body to quake again. Bonnie collapsed on the sofa so I stood up and looked down at her hot body as I peeled off my shirt. Unbuckling my belt and unzipping my pants, I pushed my trousers down to my ankles. My large erection was covered by my underwear but my state of desire was obvious. I pushed my underwear down and my cock caught in the waistband and bobbed in front of Bonnie. She stared at my erect cock as it dangled inches from her face. Bonnie stared at it as if she was looking at the first cock she had ever seen in person. I reached down and pulled her closer to me so that her mouth was now on a level with my cock.

“Your turn,” I said as I pushed my cock toward her mouth.

“I don’t like to suck cock,” Bonnie said acting out her reluctance.

“Well make an exception this time,” I replied firmly.

“Please don’t make me do it,” she begged.

“I’m not going to make you do it. I want you to want to do it. Just suck it for awhile until I am really hard. I won’t cum in your mouth if that’s what you are worried about,” I told her trying convince her to suck my cock.

Then I reminded her, “After all I did eat your pussy and lick up all your love juice.”

Bonnie reluctantly moved her head forward and kissed the head of my cock. Then she licked up and down the shaft and all around it. Eventually, after more urging on my part, she took about four inches of my cock into her mouth. In spite of her suspect reluctance, Bonnie was clearly an experienced cocksucker. She clearly knew her way around a cock and she seemed enamored with mine as she loved it with her mouth. As I looked at her distraught face sucking my cock I thought about my promise to not cum in her mouth.

“Yeah I won’t cum in your mouth tonight but before this weekend is over you will taste it and feel my seed coat your rectum,” I thought to myself.

As I lifted Bonnie’s chin up and my cock slipped from her mouth she spoke, “Can we go upstairs to my bedroom?” she asked hopefully.

“I thought that you would never ask,” I teased.

Bonnie led me to her bedroom and I watched her fantastic ass as she walked up the stairs in front of me. Her beautiful shapely ass undulated as she climbed the stairs and I felt that familiar surge in my loins. I wanted to throw her down right on the stairs, shove my cock all the way up her ass and fuck her until I filled her rectum with semen. But I knew better, so I watched her shapely bottom with each step she took up the stairs. I knew that I wouldn’t be happy until I fucked her ass that weekend.

I followed her up the stairs and into her bedroom. Bonnie pulled down her bed covers and got in bed on her back. She spread her legs slightly and looked apprehensively at my erect cock. I got on the bed between her thighs and nestled my cock at the opening to her pussy. I moved the head of my cock around her vulva and gently prodded her outer cunt lips. Bonnie moaned softly as her pussy got increasingly wetter. Satisfied that she was wet enough I eased my dick in a little parting her labia and finding the entrance to her pussy. I pushed more of my cock into her and in spite of her wetness she was still very snug. For the next several minutes I pushed in and pulled out, each time pushing a little more of my shaft into her sopping wet hole. Finally my cock sank all the way into her snatch causing Bonnie to gasp aloud. Then as I began to saw my dick in and out of her, Bonnie wrapped her legs around my lower body and humped her hips up at me. As I picked up the pace I made sure that my cock stayed in constant contact with her clit.

Bonnie surprised herself with another quick orgasm but I kept right on fucking her and she came multiple times in succession. Her pussy was flooded with her cunt juice and I could feel my cock soaking in her nectar as I pushed it all the way in. Bonnie was experiencing a continuous string of orgasms which had her body thrashing and jerking about as they led up to her final crescendo. Her body stiffened and she grabbed my shoulders as she wrapped her legs even tighter around my torso squeezing my lower body.

“Oh God, I’m cumming again, hold me, please hold me, oh, oh, please,” she cried out as a thunderous climax ripped through her body.

Bonnie stiffened at first pushing her hips toward mine and the she went out of control. Her hips humped rapidly up and down as her body thrashed about. She was grunting and groaning and gasping for air as she reached her crescendo. All her fanatic actions accelerated my own orgasm and I flooded her womb with barrage after barrage of semen. I plowed my cock into her as far as I could as I released a steady flow of spunk into her pussy. We both humped each other furiously until our orgasms subsided. I kept my weight on my elbows as I lay on top of her so as not to crush her body with my weight. Bonnie’s vaginal muscles clenched and unclenched around my shaft milking my cock dry.

Her cunt was a receptacle holding our combined juices and my cock felt as if it bathing in warm oil. My cock slowly deflated and slipped from her tight pussy with an audible sound. Our juices flowed out of her pussy as soon as my cock slipped from her hole just as if a stopper was pulled out of her. I rolled to my side along side of Bonnie and flopped on my back.

“Oh my, I haven’t cum like that in a while. It was a little scary,” she sighed and then added.

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 always 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.

“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 cum soaked pubic hair and I felt my cock starting to harden. Bonnie 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. Bonnie 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.

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.

Bonnie thought that I was preparing her ass for my cock when she said, “Please don’t. I don’t like anal sex.”

“Don’t worry,” I assured her, “I will just play with your ass as I fuck you.”

Now with my cock in her pussy and my finger in her ass I was approaching another orgasm. I could it building in my balls, travel through my scrotum and splash the insides of her vagina with my warm semen. As I came in her pussy I thought to myself yet again, “Just wait until you feel my warm seed fill your ass tomorrow night.”

On Saturday morning I woke up first with a piss hard-on. This happened frequently to me when I spent the night with a hot woman. With this piss hard-on I was able to fuck for quite awhile without cumming and until the bladder pressure got so intense that I had to relieve myself. I rolled over toward Bonnie and started caressing her body. She rolled on her back and I went to work on her firm tits and hard nipples. She cooed from the titillation and gradually woke up. Then I moved between her legs and slid my erect dick in her pussy.

The fit was tight again so I moved slowly and gently working my cock into her. Bonnie got wet quickly and my cock was soon sliding in and out of her hot cunt. As she had done before she wrapped her legs around my lower body and her arms around my back as she humped back at me. I fucked her through multiple orgasms just as I had done last night except that I didn’t cum. Bonnie arched her back and her body shook with the intensity of her climax. I kept fucking her and she had another continuous string of orgasms before her body stopped moving of its own accord.

“Please stop, let me rest, I can’t cum anymore,” Bonnie cried out, “Walt please stop, please.”

I stopped fucking her honoring her plea and I slowly slid my still erect cock from her. I headed into the bathroom to relieve the pressure of my piss hard-on and then I opted to take a shower. Bonnie joined me in the bathroom once she heard the shower running. I invited her to join me in the shower. Bonnie and I soaped each other’s body and I loved running my soapy hands all over her fantastic tits and ass. Bonnie played with my erect cock and lathered it up with soap. I turned her toward the shower wall and slid my cock into her pussy from behind. Bonnie braced herself against the shower wall as I fucked her pussy until I came shooting another good sized load into her.

We finished showering and Bonnie douched all the semen from her body. Afterwards we got dressed and went out for breakfast and spent the day together. That evening we had dinner at the Wine Cellar her favorite restaurant. As we drove back to her condo Bonnie was very amorous as the wine had an obvious effect on her. When we arrived we went straight to her bedroom, undressed and got in her bed. I moved Bonnie into a 69 position and ate her until she came. Once again she came quickly and thrust her pussy at me as I ate her dry. She sucked my cock without my urging this time but I still did not cum in her mouth.

I rolled Bonnie on her back and slid between her legs. My cock slid in easily this time and I fucked her silly before finally shooting my load in her pussy. Bonnie really came hard again as the orgasm ripped through her body. She was a very sensuous woman. We lay together and I played with her tits and nipples and worked them into a state of arousal. Bonnie cooed as I worked on her tits, rubbed her tummy and played with her soaked pussy.

Once again I got hard from the foreplay and rolled her over on all fours. Bonnie agreeably moved into the doggy position and accepted my cock in her pussy. As I fucked her slowly I rubbed her tits and played with her asshole. I easily inserted one finger in her ass and then with my other hand I diddled her clit as I fucked her from behind, Bonnie went wild again with all the stimulation and she began bucking her hips as her orgasm took over her body. As she was bucking I slipped my cock out of her pussy and quickly pushed it in her ass. Bonnie bucked and humped through her orgasm before she reacted to my cock in her ass.

Bonnie put on her reluctant act, “No please not that. Take it out. You know I don’t want to do this. Please take it out!”

But I didn’t take it out and I ignored her pleas as I pushed more of my cock into her ass. I added more saliva and pussy juice as I fucked her and shoved more cock into her ass. Bonnie tried to break loose but I held her hips firmly. Another push and my entire cock went all the way in her ass. Her asshole opened up from the reaming and I was then able to slide my cock in and out with ease. I was convinced at that moment that she had been butt fucked before. I marveled at her shapely hot ass as I watched her impaled on my cock.

“Walt please don’t, I don’t want to do this. Please don’t cum in me,” Bonnie acted again but not as urgently this time.

Once again I ignored her pleas and I picked up the pace. I could feel my own orgasm approaching and I knew it would be a big one since I was so turned on fucking Bonnie’s beautiful ass. Her ass had loosened up and my cock was sliding easily in and out of her rectum. My hips slammed into hers and her ass jiggled as my cock went balls deep into her asshole. I felt my balls tighten so I pushed my cock all the way in her ass and then I released torrents of semen into her rectum. Stream after stream of semen filled her asshole as I flooded her bowels with my load.

I realized that we were both motionless and I had my cock buried all the way up her ass. Then I began to fuck her ass slowly again and I pushed my copious load around in her rectum. As I withdrew my softening cock from her ass, gobs of spunk trickled out and ran down over her pussy lips and inner thighs. Bonnie flopped facedown on the bed and I knelt there watching my seed ooze out of her shapely ass.

“Why did you do that to me? You know I didn’t want that. I told you that I don’t like anal sex,” she whimpered.

I thought to myself, get used to it but I said, “You always say that but you know that I can’t resist your ass. It is so beautiful, so hot, so inviting.”

“I don’t want you to ever do it again. I don’t like it,” she said as she always would.

I had knew that she had been butt fucked before me since my cock went in fairly easy with the right amount of lube and she did not complain of any pain. Bonnie got out of bed and went into the bathroom to clean up. When she returned we cuddled in the spoon position and we fell asleep without any more conversation. I woke up at about 3:00 AM with a piss hard-on but this time I went to bathroom and relived myself. While in the bathroom I located some lotion and I put an ample amount on my cock before returning to bed. When I got back in bed I snuggled up to Bonnie and slipped my lotion covered cock into her ass. I had both hands around her body so I played with her tits and fingered her pussy as I slowly fucked her ass. Bonnie woke up and quickly realized that I was back in her ass. “Oh not again, please no,” she whispered.