tagAnal14 Memorable Anal Encounters 04

14 Memorable Anal Encounters 04



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).


In 1977 I decided to become a certified SCUBA diver. I had dived when in the Marine Corps but my last dives were in 1962. I did my classroom and swimming pool work in the Midwest and received a referral letter form the SCUBA school so that I could do my open water test in the Cayman Islands. There was another student in my class named Beverly.

I relaxed on the beach that afternoon after completing my certification and checked out the hot bikini clad bodies that were already spoken for. Late afternoon, I showered dressed and headed to the bar. Shortly after 5:00 PM Beverly and a couple of dive instructors entered the bar. Beverly spotted me and she and the instructors made their way over to me. The instructors congratulated me and Beverly on our certifications and I bought the first round of drinks. In fact I bought all the drinks that evening but at least the guys didn't stay that long.

I studied Beverly closer that evening and I liked what I saw. It must have been a combination of the beer, atmosphere and the fact that there were not any available single women to my liking at the resort. Also Beverly's ass looked good in her tight shorts and I wondered if she liked anal sex. Beverly had a good sense of humor and the more she drank the funnier she became. I sensed that she was out for a good time that evening. She told me a funny story that opened the door for me.

"One night Rory and I, that's my boyfriend back home in the UK, were sitting around naked drinking beers. I felt this awful sting on my ass. I yelled and smacked at something that bit me," Beverly began.

"Then Rory asks, what happened? I tell him that something bit me on my ass and he says let's have a look. So I roll over and show him the bite on my bottom and he says something bit you on your bum. So I say what do you think I just said?" Beverly told me laughing all the while.

She had me laughing as much at her delivery as the story itself. Beverly then continued, "So Rory keeps staring at my bum as if he hasn't seen it before. So I say are you going to keep staring at my bum all night?" Beverly said breaking into laughter once again.

I was laughing just as hard as she went on with the story. "So anyway Rory says we better see the doctor because the swelling was getting worse. We hop in the car and drive over to the emergency room. The doctor comes in and asks what the problem is and I tell him that a spider bit me on my bum. He says let's have a look so I roll over and show him my bottom. Then the fucking genius doctor says it looks like something bit you on your bum," Beverly manages to get out laughing hysterically.

At this point I am in stitches as well and we are both laughing out loud and Beverly continues, "So, so, I say to the doctor, that's what I told you. The doctor kept staring at my bum and I asked him if he was going to do anything except stare at my ass."

Beverly had tears in her eyes from laughing so hard and I was splitting a gut again more from her delivery of the story with her accent. "So what do you think the doctor does? He goes and gets some more medical staff to come in and look at my ass. So now I laying there with five people looking at my bum, but not a one of them are doing anything. So I ask them if they think that I just came down to the emergency room to show you my bum. They all start laughing and I start laughing and Rory is laughing. So now I am on the exam table with my ass in the air with five people looking at it and we are all laughing," Beverly leaned into me and roared out loud.

I put my arm around her as we laughed and then I said, "Well you have to forgive them because after all you have a nice ass."

Beverly then looked up at me and she was not laughing now. I was afraid that I had offended her but she leaned in and whispered, "Do you really think that I have a nice ass?"

"Absolutely, of course I have only seen the shape of it in your bathing suit or shorts. I haven't been as fortunate as the medical staff to see it bare," I replied.

"Would you like to see it?" Beverly asked as she moved her hand over my thigh. "Can I count on you to be discreet?"

"Yes to both questions," I whispered in her ear.

"Let's go to your room but we can't be seen walking in there together," she told me.

I told her my room number and she walked out of the bar first. I settled my tab and then finished my beer before I left. I walked over to the building where my room was and as I did Beverly appeared out of the shadows. She had waited until I had my key in my hand and I was close to the room. I opened the door and she quickly ducked inside.

Beverly made a bee line for the bedroom shedding her clothes along the way. She hopped in bed totally naked as I finished removing my clothes. Beverly was ready as was I so there was no need for foreplay. I slipped right between her thighs and my cock slid into her wet pussy like a hot knife through butter. Beverly moaned as my cock entered her cunt and she wrapped her arms and legs around me as I went deep into her. We fucked slowly at first and then picked up the pace. Beverly had a mild orgasm along the way to a massive more intense one. Her body rocked and gyrated as she screamed in ecstasy and it was all I could do to hold on as she bucked up at me. Then I felt my surge and I drilled deep into her pussy just before I unleashed a massive cum load. I felt my cum shoot out of my cock deep into her womb and Beverly held me tighter as I came in her.

We stayed together for several minutes with my cock buried deep in her pussy and her arms and legs still holding me tight. Beverly and I separated and I rolled over on my back. She surprised me when she moved back down and took my cock in her mouth. Within minutes she had me rock hard proving that she was an accomplished cock sucker. I was anxious to get at her ass all the while wondering if she would let me fuck her in the ass. I moved her to all fours with her ass elevated and she placed her head on the mattress turned to one side so she could see me. I started playing with her pussy and her curvy ass lubricating her asshole with her own cunt juice. Beverly moaned and cooed as I fingered her pussy and her asshole simultaneously. I tired to get her asshole wet enough with her juices and my saliva so that I could fuck her ass.

I knelt behind her and tried to insert my cock in her ass but it just wouldn't go. Afraid of hurting her I tried more pussy juice and saliva for lubrication but to no avail. My cock of 7+ inches long and 5 inches around just wouldn't go. There are times when it feels bigger and this was one of those times. I was fingering Beverly's ass when she spoke.

"You are going to need some cream to get that thing in my ass," she whispered.

I got off the bed to retrieve the lotion from the bathroom. As I did I realized that Beverly was going to let me fuck her in the ass. I returned to the bed and put an ample of amount of lotion in her asshole coating the tiny puckered opening of her anus and lubricating the rim. I added my saliva to my lotion covered cock and nestled my dick against the entrance of her rectum momentarily before easing it inside her ass. I could feel my cock struggle to stretch the resistant muscles. My dick head burrowed in and her rigid passageway soon yielded to the determined action of my cock. Beverly moaned as my penis filled her hole.

"Go slowly at first you're big," she said sexily.

I fucked her with long and deliberate strokes until my cock was sliding easily in and out of her ass. I caressed her shapely buttocks as I watched my penis move in and out of her rectum worming around inside of her curvy ass. I caressed her small tits and tweaked her nipples as I leaned over her body and whispered in her ear.

"You know Beverly I can see why all those people were looking at your bum. You have a very hot ass and I love fucking you in your hot ass."

My hands freely roamed her body and I pulled her hips drawing her backwards impaling her on my inflated member. I reached for her pussy to finger fuck her and diddle her clit but I found Beverly's hand already buried in her womb. Suddenly I felt my cock inside her ass swell up and I started pumping faster. Within minutes I knew that Beverly felt the warm fluid being squirted inside her anus and she immediately started to cum herself. I grunted as my whole body became stiff and I slammed my cock harder into her. Beverly writhed around and her body arched off the bed as a climax of massive proportion tore through her loins. My cock slipped from her ass with an audible pop and I flopped down on the bed next to her. Beverly 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 need to cum again."

I rolled over and got between her legs and blocked out that fact that I had cum in her before. 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 Beverly's mound. It felt so smooth and warm and I knew I had achieved the desired effect from her moan I know that Beverly 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. Soon I was lapping up as much as I could as fast as I could.

Beverly went wild and started bucking and moaning loudly. She let go of her own fleshy hood and pulled my head to her pussy as she cried out in ecstasy. I sucked her clit as deep in my mouth as I could and Beverly humped my face for all she was worth. I was thrilled that I was able to get her that excited and I sucked harder and played with her wonderful clit with my lips, tongue and teeth. I don't know exactly how many times Beverly came but finally she collapsed on the bed, her body in spasms.

I lay next to her and stroked her body my hands moved freely over her tits and pussy mound. She rolled toward me and embraced me and yelled for me to hold her tight.

"Hold me, oh please hold me," she pleaded as her orgasm and spasms subsided.

I had never seen anyone cum that hard before and I was briefly worried that she had injured herself. My fears were short lived when she finally calmed down and spoke to me.

"That was incredible I haven't cum like that in a long time. You really know how to eat pussy," she said with a sigh.

We lay there for awhile making small talk and then Beverly started stroking my cock. Now at the age of 36 it was very unusual for me to cum more than twice in a fuck session, particularly after having a couple of drinks. In fact I usually could stay hard for a long time before my second cum which allowed me to pleasure my partner thoroughly before achieving my own orgasm. Beverly added some body lotion as she kept stroking my cock and soon had me hard again.

"I like playing with your cock. You have a big cock," she told me.

"It's not that big," I replied although I was very comfortable with my manhood.

"It's the biggest I have ever had in my ass," she said with a sultry tone.

"Well there are plenty of cocks bigger than mine," I assured her.

We continued our conversation as Beverly continued to stroke my cock. I learned that she had first been ass fucked before she met Rory in London. Beverly was working in London at the time and she went out with two guys from the office. They took her back to their place and one fucked her ass as she blew the other guy. She took to ass fucking after that but she was very selective about who allowed in her ass. Rory did not like butt fucking. She also told me that this was the first time she had anal sex with anyone since dating Rory. I shared with her that I loved fucking a beautiful ass and that hers was right up there with the best of them.

"All this talk and playing with your cock has got me hot again. I need to sit on your dick," she announced.

Beverly straddled my body and lowered herself onto me as she held my tool and aimed it at her vagina. My hard cock slid easily into her womb and she emitted a small gasp as it filled her hole. Beverly rocked back and forth on top of me as I held on to her curvy ass. I stroked her ass cheeks and molded her firm buttocks in my hands as she picked up the pace fucking herself with my dick. Beverly started moaning as she fucked faster and faster. I sensed her pending orgasm and then she yelled out.

"I am going to explode. Oh, Oh hold me, please hold me tight," she screamed.

Beverly collapsed on top of me her body quivering from the intensity of her orgasm. I could feel her juices coating my cock as it remained buried in her womb. It took a few minutes for her to regain her composure and she just lay on me and cooed. Eventually she rolled off of me and lay on her back next to me.

"Can I stay here tonight?" she asked in a hopeful tone.

"I would love for you to stay the night," I told her.

Later she rolled over on her side and faced away from me. I draped my arm over her body and cupped her small breast. Her ass was pressed into my body and my soft cock nestled against her buttocks. We fell asleep in that position and slept soundly through the night.


Wednesday morning I woke up with Beverly stroking my cock. She smiled at me when she saw I was awake and then she lowered her mouth to my cock and deep throated me as she had the night before. I had a tremendous urge to piss but I knew I couldn't as long as my cock was hard and I couldn't cum until I took my morning piss. I decided then to fuck Beverly into submission that morning. I rolled her over and got on top of her and slipped my early morning erection into her moist pussy. I started fucking her slowly and gradually picked up the pace as she moaned and groaned with desire. Beverly did not know what she was in that morning and I was determined to fuck her brains out. I could fuck for a long time without cumming the first in the morning with my piss hard-on. As I pounded Beverly's pussy she had a continuous string of orgasms. She was screaming and thrashing in ecstasy. Beverly held me tight, dug her heels into my back and muffled her screams in my shoulder as I pounded her pussy. Finally she shook uncontrollably, screamed and collapsed, her body going limp on the bed.

"Please stop fucking me, no more please. I can't cum anymore please let me rest," Beverly pleaded.

I eased my still hard cock out of her cunt and I actually heard her pussy sucking as if it was gasping for air. I slid off the bed and went into the bathroom to take my morning piss. When I returned to the bedroom Beverly was in the same position that I had left her. I got back in bed and rolled her over on her stomach.

"Please Walt let me rest awhile," Beverly begged.

"Relax and I will give you one of my famous massages," I told her.

I took the lotion from the night stand and applied it to her back and shoulders. I massaged her neck, shoulders and back rubbing the lotion in and relaxing her body. Then I moved down to her calves and massaged her aching legs. I worked my way up to the back of her thighs and massaged them deeply. Beverly moaned and cooed under the manipulation of my hands and I knew that she was enjoying the massage. I next moved my hands to her buttocks and massaged her glutes as I knew they were fatigued from all of our fucking the past two days. Beverly involuntarily tightened her butt muscles as I massaged them and I felt my cock get hard again.

I put more lotion on Beverly's ass and worked some of it into her crack. Beverly raised her ass slightly and I slipped a lubed finger into her bung hole. Beverly gasped at the intrusion but then relaxed and enjoyed the stimulation. I added a second finger and Beverly gasped again. As I worked my two fingers in her ass my cock had become fully erect again. I lifted Beverly by her hips and she allowed me to lift her ass higher as she kept her head on the bed. I was sure that she knew I was going to take her ass again and she offered no protest.

I lined up my throbbing cock at the entrance to her ass and pushed it in until the head cleared her sphincter. Once again Beverly gasped at the intrusion but she did not resist. I eased my cock into her ass inch by inch until it was completely buried in her anal channel. I started slowly as I had before and then picked up the pace. Watching Beverly's ass impaled on my cock as I fucked her sent a chill through my body. My own orgasm, the first one of the day, was building in my balls and I knew it would just be a matter of minutes before I ejaculated.

My body stiffened, my balls tightened and the first stream of cum entered Beverly's asshole catching her by surprise. I pulled my cock from her ass as I continued shooting cum at her asshole. My semen bounced off her anus and her buttocks and then ran down over her pussy lips onto the bed sheets. After shooting my last stream at her aperture I shoved my cock back into her ass. Beverly once again milked my cock with her anal muscles and drained it dry. My cock stayed hard and I was sure that I could fuck her again but I withdrew my cock from her ass. Cum bubbled from her butt hole and trickled down over her vulva. There was more cum this time since I had shot my first load deep into her rectum. Beverly worked her sphincter and squeezed the semen from her ass as I watched. I then fingered her ass and pussy at the same time.

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