tagAnal14 Memorable Anal Encounters 02

14 Memorable Anal Encounters 02



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.


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).


It was in Pittsburgh that I met Terri in 1979. I had joined a software company that year and I was attending a product training session. There were a number of customers at the session as well but none of them really appealed to me at first. After the third day I had dinner with a couple of attendees and a young woman named Terri seemed attracted to me. After dinner I invited her to have a night cap with me at the bar. From there things moved quickly and it was obvious that she was horny that night.

Terri was wearing a tasteful business suit and it fit her nicely. I guessed her to weigh about 100 pounds and I noticed her nice legs. The skirt fit her snugly showing the curve of her cute ass. Teri was not a beauty by any means but she was attractive in a different way. We left the bar and she accepted my invitation to my room.

Once in side we were kissing on the bed and I began to remove her clothes. In spite of her horniness she was shy. I removed her jacket and blouse and noticed that her skin was lily white. She obviously was not a sun lover. I removed her bra and bared her small tits. When I kissed her breasts and sucked on her nipples she cried out. It was apparent that her tits were very sensitive but I suspected that they didn't get that much attention. I unfastened her skirt next and removed it leaving her in her pantyhose and panties.

Terri crooned as I removed her hose and panties together and now she lay naked before me. I kissed my way up her legs and then spread them to look at her pussy. She had a small tuft of reddish brown hair above her nice looking pussy. I dipped my tongue in her tasting her and found her to taste sweet. I ran my tongue over her clit causing her to cry out again. Just a couple of swipes and she exploded.

"Oh God this is a quick one," she cried out.

I held her hands at her side and sucked on her twat driving her wild. Terri thrashed all over the bed and then her orgasm subsided and she was still. I stood up and removed my clothes and I followed her eyes to my cock. She seemed nervous about my size so I knew that I should take it easy with her. I moved between her legs and that's when I discovered what made her nervous. I could not get my cock in very deep as she had a shallow vagina.

"Oh I should have told you. The doctor said I would have problems because I'm not very deep," she whimpered.

I felt sorry for her and told her not to worry about it. "I can still cum but I don't want to hurt you," I assured her.

I held my cock in my hand and ran the head along her clit and let it dip in every so often. Terri was getting excited again and she climaxed before I was close to cumming. "How about oral, do you like that?" I asked.

"I can do that," she agreed and moved down to take my cock in her mouth.

Terri was a willing but inexperienced cock sucker and she tried to please me. She was on her belly lying across the bed as she sucked on my cock and I began to play with the cute ass. I fondled her cheeks and dipped my finger into the crack. "Have you ever done anal?" I asked.

"No but I am willing to try if it will make you happy," she replied.

"Let's give it a go. I promise I will be gentle with you. If you want to stop, tell me," I told her.

I moved behind Terri and lifted her hips into the air. She kept her head on the bed turned to one side with an apprehensive look on her face. I got out of bed and got the lotion from the bathroom. Terri's ass looked very inviting and I lubricated it thoroughly. She moaned softly and the penetration of my finger and soon relaxed with the intrusion. I was able to add a second finger and in spite some discomfort Terri didn't complain. I knew it was going to be a challenge for her to take my cock in her ass. I was getting more and more turned on fingering her bum and I had to try and fuck her.

"It's time to fuck your hot ass."

"I'm scared," Terri said nervously.

"Relax, I won't hurt you."

I poured more lubricant on her ass and worked it into her asshole. Terri arched her back and pointed her beautiful ass back at me. I then coated my entire cock with the lube and placed it at entrance to her anus. I pushed forward and the soft mushroom head squeezed into Terri's tight asshole. Terri winched in pain as her asshole was stretched wider than ever and she gasped, "Go slow let me get used to it."

Satisfied that she was well lubed I straddled her hips and dipped my slick cock into her pussy to coat it with juices and then I eased it into her ass. My cock head slipped past the moistened sphincter and the spongy head disappeared into her ass. Her anal ring snapped closed behind the cock head and I marveled at the sight before me. I only had the head of my cock in her and she lifted her hips as if she wanted more.

"Not too deep at first and then go deeper little by little," she whispered as a caution to me.

My cock felt bigger than it ever had as I eased more of it into her anal passage. I watched as it stretched her open and entered her slippery hole. I continued my slow penetration until the entire length of my shaft was balls deep in her ass. Terri gasped and grabbed the bed sheets as I hit bottom and then she moved her ass in time with my thrusts.

"Let's fuck on our sides," she rasped.

I rolled both of us to our left side and settled into the spoon position with my cock buried in her asshole. My left arm came around and fondled one of her tits and tweaked her nipples as my right hand sought out her pussy. I pushed two fingers into her pussy and rubbed her clit as I fucked her ass and played with her tits. Terri was going wild as her orgasmic, constricting muscles gripped me firmly.

We fucked slowly as she arched her back and we fitted together perfectly. Her gasps were intermittent and interrupted with cries and sobs of pleasure. Her ass felt so snug at that moment that I wondered how the semen would ever get out of my cock. I fought to hold back my orgasm as long as possible but the undulating walls of her asshole were just too much. I felt the familiar boiling in my balls and I thrust into her as the first blast of cum exploded into her rectum. I barely heard her pleas for me to fill her ass with cum as her contractions milked every drop from my cock. I continued to fuck her slowly and I enjoyed the new feeling of warm semen surrounding my cock in her sheath.

"I love the feel of your warm cum in my ass. I never thought that I would but I do," she sighed as my cock remained nestled in her hole.

For some reason I stayed hard and I kept right on fucking Terri's ass. I pummeled her ass as I sought out another ejaculation. Terri's ass was loser now and slippery from the combination of the lube and my semen but she was still snug around my cock. Once again I stiffened and fired a load into her rectum. I could feel my cock pulsate again as it released my man seed deep into her anal recess.

We lay still for a few minutes recovering from the intense fuck session. I had forgotten about my cock in her ass until it had softened and slipped from her hole. I felt my wet cock drop on my thigh and I knew that cum was trickling out of Terri's asshole. We rested several minutes and then I suggested a shower. We both showered together and washed in each other's body. Then Terri put her clothes and back on and went to her hotel room.

The next evening it was déjà vu as Terri looked forward to being with me again. This time I went to her room. She was already naked when I arrived and she quickly ushered me in her room. She ran and jumped in her bed and wiggled her ass at me.

"I douched both my ass and pussy for you tonight," she uttered in a sultry tone.

I walked toward the bed and by the time I got my clothes off my cock was rock hard. I leaned over and licked Terri's pussy from behind driving her wild. I could tell that she had dabbed a very fragrant perfume between her thighs and on her ass cheeks. 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 my fingers in her tiny pussy. She started whimpering, gasping and directing the action.

"Oh my God, do it again. Lick my anus; stick your tongue in there. Eat my pussy, tongue my ass, rim me, oh yessssss," she cried out and then added, "I'm all yours. Do anything that you want to me."

I let my saliva trickle down over her anus and pussy. I placed my mouth on her and drank up my own spit swabbing her pussy and ass in the process. I repeated this several more times until Terri seemed to go into convulsions with her first orgasm of the evening.

"Oh I loved the way you tongued my ass. It felt so wonderful," she uttered in an exhaustive voice.

"I loved doing it and it looked incredibly sexy as it glistened with oil. I remembered that you told me that you had douched and it looked so clean," I told her.

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 put her head on the mattress and turned to the side so that she could watch. 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," Terri exclaimed!

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 shapely 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 the large mushroom head slipped past the ring and into her ass. Terri 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 anything," 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 eight plus inches were tightly packed up her ass. Terri 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. Terri 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. Terri was thrashing around uncontrollably, gasping and moaning with pleasure. When I reached underneath her to stroke her clit she exploded with another orgasm.

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 bed cover begging me to cum.

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

I took firm hold of her hips and slammed once more full force into Terri'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.

I didn't stop fucking her as my cock stayed hard. I knew that I could cum again so I kept at her ass. Terri was groaning and whimpering as I drilled her ass. Soon she stopped moving but remained on all fours impaled on my cock. I could feel my previous load squishing around in her rectum and it was a bit of a turn on. I enjoyed watching my cock slide in and out of her curvy ass. I caressed her shapely buns as I fucked her and I loved watching them jiggle when our flesh slapped together. I felt another surge in my loins and within minutes I was shooting another impressive load into her ass. My body stiffened as I pushed my cock in as far as I could and shot ropes of semen into her rectum.

Terri anal muscles involuntarily clenched around my cock and milked the semen from it. Amazingly I stayed hard as her muscles massaged my shaft and I slowly began to move my hips again. Terri's body was almost lifeless at this point and she wanted to lie down but I held her by her hips as I continued to fuck her ass. I don't know how long we fucked but my thigh muscles were aching and cramping.

I pulled out of her ass as Terri lay on the bed utterly spent. I slumped down next to her quivering body. I looked over at Terri and I noticed my seed running out of her asshole. It was a very erotic sight as it seemed like an endless stream oozed out of her anus and down between her inner thighs. Terri whimpered as she lay face down on the bed. I reached over and stroked her beautiful ass lovingly.

Thirty minutes had passed before either of us spoke. "I feel like I just had an enema," Terri said softly.

"It feels like your cock is still in there," she said as she stroked her ravaged ass with her hand.

I reached over and caressed her ass as I thanked her for a wonderful time. "That was great anal sex," I murmured.

"I have to go to the bathroom," Terri announced as she swung her legs out of bed.

I watched her walk into the bathroom and I again admired her shapely legs and curvy bubble butt. I noticed that semen was running down her legs but she didn't seem to care at the moment. Terri was in the bathroom several minutes and then I heard the water running in her tub. She came back out and she looked drained.

"I need to take a long hot bath and soak my body. Do you mind?" she asked.

"Not at all, I have an early flight in the morning and I could use a good night's sleep," I told her.

I kissed Terri goodnight and got dressed while she was in the tub. I went back to my room and set the alarm for morning. Early the next morning was up before the alarm. I showered, dressed, packed and checked out of the hotel. I had breakfast at the airport and as did, I thought about how things had turned out. I had not expected to get laid when I first arrived and I certainly had not expected to have great anal sex. Taking Terri's anal virginity was a thrill for both of us and I was flattered that she so willingly gave up her ass to me. She certainly made up for the limitations of her vagina and proved to be a good lover. I never did run into Terri again after that week but I never forgot those two nights of great sex.


It was a Tuesday evening in October 1978 and I had worked late at the office. I decided to stop for a drink at a bar called the White Rabbit where I had gotten lucky sometimes. There was nothing going on when I got there but I spotted Dick a friend of mine. I joined him for a drink at the bar and it was nearly 9:00 PM when I was about to call it a night. Just then a cute woman with pixie haircut came in by herself. She could have sat alone at the bar away from us but she chose to sit near Dick and me.

She smiled as she got up on the bar stool and ordered a drink. "That's on me I told Tommy the bartender."

"Thank you," she accepted and smiled again.

Upon a closer look I guessed she was in her early to mid forties. She was somewhat short close to five feet tall and she had a decent figure. Her drink arrived and she held up the glass in a toast and said, "I'm Rita and thanks for the drink."

I held my glass up and said, "Your welcome, I'm Walt and this is Dick."

Over the next 20 minutes or so we got acquainted and had another drink. Dick sensed where things were headed so after his drink he excused himself and left. He whispered to me on the way out. "I'm going to stop at the lounge if things don't work out here, I'll see you there." The lounge was another bar where we often stopped but many people from the company went there and it wasn't the most discreet place.

Rita and I continued our conversation after Dick left and I learned that she was a nurse at the hospital. I saw her glass was empty so I offered her another drink.

"No thanks, would you like to come to my place for a nightcap?" she offered.

"Definitely," I accepted and I finished my drink and paid the tab.

Rita walked ahead of me out of the bar and I admired her shapely ass as it filled out her pants. She certainly was a confident woman. We got in our cars and I followed Rita to her apartment complex. I parked my car and walked with her to her apartment. Once inside she said, "Do you really need that drink?" as she pulled her top over her head.

"No, I don't, I replied as I watched her undress

She pulled the top over her head and folded it neatly and placed it on the chair. Next she peeled off her pants and placed them on the chair as well. Then she took off her bra and I admired her shapely figure, her medium sized breasts and her muscular legs. Finally she smiled at me as she removed her panties and faced me in her naked beauty.

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