14 Memorable Anal Encounters 03
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.
Peggy 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 Peggy humped my face for all she was worth. I was excited 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 Peggy came but she finally pushed me away as she collapsed on the bed, her body in spasms.
I lay next to her and stroked her body my hands moved freely over her firm small tits and pussy mound. I tweaked her hard little nubs as they pointed straight out from her breasts. 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 orgasms and spasms continued.
As we lay there for awhile talking, Peggy started stroking my cock. Peggy added some saliva from her mouth as she kept stroking my cock. Next Peggy 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. Peggy 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. Peggy 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.
Peggy 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. I too exploded with my first load of the night and I flooded her pussy with my semen. 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. I was still hard so I rolled over on her pushing my cock back into her pussy. I fucked her until she pleaded with me to give her pussy a rest.
I pulled out of Peggy and then rolled her over on all fours. I slipped my cock back into her pussy and pounded her from behind. I loved looking at her shapely ass as I fucked her and I even thought about fucking her in the ass. However I didn't want to push her too fast so I resolved myself to focus on her pussy. I massaged Peggy's beautiful ass I fucked her doggy style until I came in her pussy for a second time. Peggy had her head turned to the side and emitted soft sounding murmurs as I emptied my balls into her twat. I pulled my softening cock from her and then flopped down next to her on the bed.
"I think I need to get cleaned up and dressed. I have an appointment in the morning," she said and then asked. "May I use your bathroom?"
"Of course, in fact I'll shower with you," I replied.
We both showered together and washed each other but avoided having anymore sex that night. Afterward we got dressed and I drove Peggy home. I wondered what type of appointment that she had on a Saturday morning that she couldn't cancel but I never asked her. I was pleased with the way the evening had turned out and I hoped that there would be more.
SATURDAY SURPRISE
I was sitting in the living room when the doorbell rang and for some reason I expected it to be Frank. I was wrong but pleasantly surprised when it was Peggy. I invited Peggy in for coffee and she willingly accepted. We went into the apartment and I pored us both a cup of coffee. We sat at my kitchen table sipping coffee and chatting for several minutes. She decided to come and see me after her appointment that morning as my apartment was close by. We chatted for awhile and then I though to ask her if she would like to hang out that day.
"Peggy is there anything in particular that you would like to do today? Have lunch?" I offered.
She smiled demurely and blushed slightly when she replied, "I would like for us to make love before anything else."
"I want us to undress each other and I want to undress you first," she added.
Undressing me first would be easy since I was only wearing sweats. Peggy stood up from the chair and walked over to me. Then she pulled my sweat shirt up and off my body. I stood up as she dropped to her knees in front of me to lower my sweat pants but first she removed my athletic shoes and socks. Peggy then took hold of the sweat pant waistband and slowly pulled them down my legs. By this time I had an erection and it sprung out at her as she lowered my pants. My cock dangled in front of her face as she removed my sweat pants from me one leg at a time. I stood completely naked in front of her with my cock just inches from her face.
Peggy took my cock in her mouth and sucked it gently. She licked all around it and ran her tongue up and down the shaft. Peggy was a very accomplished cocksucker and I knew that I would soon blow my load. She sucked me deep into her mouth and swirled her tongue around the shaft of my cock. I felt my orgasm building and I warned her that I was going to cum soon.
"I am going to cum soon Peggy," I cautioned.
She took her mouth of my cock and looked up at me with those deep brown eyes and replied, "I want you to cum in my mouth I want to taste you Walt."
Peggy returned her mouth to my cock and resumed sucking it until I exploded in her mouth. She continued to suck my cock and swallow every drop until my cock was drained dry.
"Oh Walt I love your cum. It is so tasty and so much of it," Peggy sighed as she licked her lips.
Peggy then stood up still fully clothed and lifted her face up to me to be kissed. I kissed her and held her in my arms and then I began to undress her. I dropped to my knees, unbuckled her belt and unfastened her jeans. I pulled the jeans down her legs stopping to remove her shoes and anklets. Then I pulled her jeans all the way down and off her shapely legs. I then took hold of her panties and slowly peeled them down and off her legs. Peggy was trembling slightly and had goose bumps on her skin. I held her panties up to my nose and inhaled the smell of her femininity. Peggy gasped at the action. I reached behind Peggy and grasped her firm shapely ass in both my hands and pulled her toward me. She gasped again as I kissed her loins and fondled her ass cheeks. I could smell her sweet sex but I held off on licking her pussy.
I stood back up and I lifted Peggy's sweater up and removed it from her body. Then I reached behind her and unhooked her bra. I was beginning to harden again and my semi-erect cock brushed against her thighs. I slid the bra straps slowly down her arms baring her small firm breasts. Her nipples were rock hard and I couldn't resist tweaking them a little which caused Peggy to moan softly. I then turned her around so that her back was to me and I reached around and cupped her firm tits in my hands. I played with her tits and nipples as I kissed the back of her neck. My cock was now fully erect again and it brushed against her buttocks as I fondled her.
I started a slow gradual descent down the back of her body kissing her neck, shoulders and back until I knelt behind her. When I reached her buttocks I planted kisses on both ass cheeks and tickled her crack with my tongue. Peggy couldn't take anymore of my teasing so she turned her body toward me, grasped my head in both hands and pulled me against her pubes. I found her pussy with my tongue and I grabbed both of her ass cheeks as I began to lick her pussy. Peggy gasped aloud as my tongue found her clit and she held my head tightly as she experienced a mild orgasm. Her body shook and she seemed to hold onto me for balance.
"Can we go to your bedroom?" she asked breathlessly.
I guided Peggy into my bedroom and over to my bed. She immediately splayed her legs and welcomed me back to her pussy. I burrowed my tongue as deep into her as I could and then I just sort of licked and sucked my way up. When I got to her clit I used the very tip of my tongue to tickle it. I flicked my tongue over it once and then used the tip to explore the folds of flesh on either side of it. Peggy was now moaning and she arched herself so that her clit stuck out even further like a little cock. I licked it once more before I took it between my teeth and gently nibbled it.
Peggy went wild and started bucking and moaning loudly. She 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 Peggy humped my face for all she was worth. I was pleased 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 Peggy came but she finally begged me to stop as she collapsed on the bed, her body in spasms.
I was not done with her however so I eased my dick into her pussy and began to fuck her slowly. Soon my cock was sliding easily in and out of her and we picked up the pace. Peggy wrapped her arms around my back and her legs around the back of my legs. She arched her back as she humped me hard and fast and I made sure that my cock stayed in contact with her clit as I plowed her cunt. We fucked hard and long working ourselves toward an exhaustive state. I could feel my orgasm building but I did not want to cum before Peggy and I was relieved when I felt her tense up.
"Walt, hold me, hold me, I'm coming, oh, oh, oh" Peggy screamed as she reached her crescendo!
She tensed up wrapping her arms around my back and her legs around the back of my legs in a vice like grip. I held her trembling body tight and I could feel her drench my cock with her pussy juice just before my own intense orgasm. I could feel it building in my balls and then I exploded filling her with my man seed. It seemed endless as I fired round after round of hot cum into her pussy.
I remained still with my cock still in Peggy's pussy as she uttered unintelligent moans and sounds and her body quivered. Her vagina muscles were involuntarily squeezing and releasing my cock, milking all the juice out of it. My deflated cock slipped from her vagina and she flinched as cool air touched her opening.
"Oh that was incredible. You are a very good lover, Walt," she sighed.
"Well you are too and I really enjoy making love to you," I replied.
"I need to rest for awhile, my body aches so," she said softly.
"I'll tell you what, let's take a shower," I suggested.
Peggy and I showered together and I massaged her firm body as we washed. As I washed her I paid a lot of attention to her ass. As I ran my hands between her legs washing her pussy and her bottom, I slipped a very soapy middle finger into her asshole. Peggy gasped at first but then she just wiggled her bottom and smiled at me. I covered her body with shower gel telling her that it would help soothe her muscles. I also put shower gel in her ass and pushed my finger back in her bung hole. After showering we dried each other and then I gave Peggy a sweat shirt to wear. She looked so sexy with the sweat shirt just covering her pussy and ass with her shapely legs on display that I felt my cock stir again.
"Walter can we go back to your bed now?" she asked in a sultry tone.
"Of course we can," I told her.
As we walked to the bedroom I watched Peggy with her shapely legs below the sweat shirt. I could also see the slight curve to her ass. I felt my loins stir again as we approached the bedroom. Once inside Peggy stripped off the sweat shirt and flopped down on my bed face down.
At this point 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. Then I grabbed the lotion from my bedside and put an ample amount in her asshole. Peggy moaned and cooed as I fingered her pussy and her asshole simultaneously. I tired to get her asshole slick enough so that I could fuck her ass.
When Peggy didn't reject my probing I realized that she was going to let me fuck her in the ass. I 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 always found that Keri body lotion and saliva will make my cock as slippery as possible. 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. Peggy moaned as my penis filled her hole.
"Go slowly at first," she said sexily and then added, "Not too deep at first and then deeper."
I fucked her with long and deliberate strokes until my cock was sliding easily back and forth in her ass. I caressed her shapely buttocks as I watched my pecker 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, "Peggy you have a hot ass, 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 Peggy's hand already buried in her womb. She was frigging herself frantically working herself toward an orgasm. Suddenly I felt my cock inside her ass swell up and I started pumping faster. Within minutes I knew that Peggy felt the warm fluid being squirted inside her anus and she immediately started to cum herself. Her cunt walls convulsed around her own hand fucking her cunt as her anal muscles squeezed every drop from my spurting cock. I grunted as my whole body became stiff and I slammed my cock harder into her. Peggy 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. She surprised me when she covered my cock with her mouth and sucked any remaining cum from my tool. The both of us were exhausted and Peggy curled up in my arms. The two of us dozed off for quite awhile and then finally woke up after lunch time. Peggy and I then had a late lunch in the apartment. We sat around naked as we ate and chatted as it was the most natural thing in the world.
After lunch I offered Peggy a massage which she gladly accepted. I had her lay face down on my bed and I worked her back, legs and buttocks. Not so surprisingly I got an erection as I massaged and fingered her ass again. I came again when I fucked her ass and after the ass fuck I rolled Peggy over on her back and continued the massage this time working her tits, abs, legs and pubes. I finished her off with another thorough pussy eating which had her screaming my name and humping my face with her volcanic orgasm.
Peggy and I continued to see each other but I also learned that she was very sexually active and she was seeing a number of other guys. Peggy loved getting fucked in the ass and she taught me her favorite position. She liked to be kneeling on the bed straight up with me behind her with my cock stuffed up her ass. She had me guide her hand to her pussy and hold it there while she rubbed her clit and with my other hand I fondled her tits and hard nipples. Peggy would cream her own hand and I would cum in her ass filling her rectum with a massive load.
After my short three months with the company I left town for a bigger and better job. I never saw Peggy again but it had been an adventurous three months.
NUMBER 6 -- SHERRY
My best friend Ken and I went skiing for a week every year in Colorado. In 1983 we went to Aspen and stayed in a condo near Snowmass. Ken would always invite some girl that he had fucked before to join him on the trip. This year a woman named Toni showed up the second day that we were there. Toni was nice enough even though she seemed a little shy. I assumed she was slightly embarrassed that I was in the other bedroom while Ken was banging her at night.
Toni was a decent skier and she didn't hold us back. The three of us enjoyed our day on the slopes and our Après Ski. One day we stopped at one bar in Snowmass and there was a really good band there. That's when I met Sherry. She was standing alone near the bar when I asked her to dance. She smiled and accepted and we hit the dance floor and stayed out for five songs.
"I really need to rest a minute. The altitude is getting to me," Sherry told me after the fifth song.
"Sure, would you like to join us?" I asked pointing to the table we were sitting.
Sherry accepted the invitation and joined Ken, Toni and I at the table. Introductions were made and we enjoyed the rest of the afternoon together. Sherry was staying at Snowmass for two days and then heading up to Vail to see some friends there. Sherry was a strawberry blonde with a solid figure. She was about 5'6" and I guessed about 140 pounds. She was solid as a rock and had big tits. Her hips and thighs were full but you could tell she was in shape.
The three of us closed the Après Ski bar and then agreed to ski together tomorrow. Sherry said goodnight to us and that she would see us tomorrow. Ken, Toni and I went to dinner and then returned to our condo. It didn't take long for Ken and Toni to go to their bedroom and then I decided to watch TV in my bedroom.
The next day the four of us skied together and had a great time. Sherry was a very accomplished skier and was probably the best of the four of us. After skiing we all showered dressed and went to dinner in Aspen. Following dinner we found a place to dance and party and we had a good time although there was something funny about Toni that day. I sensed that Toni was jealous of Sherry being a better skier and dancer. It's funny how women can get that way at times.
The four of us went back to our condo where Sherry had left her car. I invited Sherry in and I spotted the look of disdain on Toni's face. Sherry accepted and came in for a nightcap. Toni seemed uncomfortable with Sherry in the room so she said goodnight and went into the bedroom. Ken followed her shortly leaving Sherry and me together. We sat on the sofa together with our feet up on the coffee table looking at the fire. It was a romantic setting and Sherry cuddled up to me. I put my arm around her and soon we were kissing and petting. I started to take of her sweater but she stopped me.
"Can we go into your bedroom? She whispered.
I nodded and whispered, "Yes."
We walked into the bedroom and I closed the door. I turned on the small light in the room so that we could see. The room was dimly lit but we could see each other very well.
"I want us to undress each other and I want to undress you first," she whispered.
I wasn't surprised that she wanted to do that because she was the fourth girl that had used that approach. I was all for it as I liked being undressed by a hot chick. Sherry walked over to me and then she pulled my shirt up and off my body. I stood up as she dropped to her knees in front of me to lower my pants and underwear but first she removed my shoes and socks. Sherry then took hold of the underwear waistband and slowly pulled them down my legs. By this time I had an erection and it sprung out at her as she lowered my briefs. My cock dangled in front of her face as she removed my briefs from me one leg at a time. I stood completely naked in front of her with my cock just inches from her face.
Sherry took my cock in her mouth and sucked it gently. She licked all around it and ran her tongue up and down the shaft. Sherry was a very accomplished cocksucker and I knew that I would soon blow my load. She sucked me deep into her mouth and swirled her tongue around the shaft of my cock. I felt my orgasm building and I warned her that I was going to cum.
"I am going to cum soon Sherry," I cautioned.
She took her mouth of my cock and looked up at me with those deep brown eyes and replied, "Okay, undress me now."
Sherry stood up still fully clothed and lifted her face up to me to be kissed. I kissed her and held her in my arms and then I began to undress her. I dropped to my knees, unbuckled her belt and unfastened her jeans. I pulled the jeans down her legs stopping to remove her shoes and anklets. Then I pulled her jeans all the way down and off her shapely legs. I then took hold of her panties and slowly peeled them down and off her legs. Sherry was trembling slightly and had goose bumps on her skin. I held her panties up to my nose and inhaled the smell of her femininity. Sherry gasped at the action. I reached behind Sherry and grasped her firm shapely ass in both my hands and pulled her toward me. She gasped again as I kissed her loins and fondled her ass cheeks. I could smell her sweet sex but I held off on licking her pussy.
I stood back up and I lifted Sherry's sweater up and removed it from her body. Then I reached behind her and unhooked her bra. I was beginning to harden again and my semi-erect cock brushed against her thighs. I slid the bra straps slowly down her arms baring her large firm breasts. Her nipples were rock hard and I couldn't resist tweaking them a little which caused Sherry to moan softly. I then turned her around so that her back was to me and I reached around and cupped her firm tits in my hands. I played with her tits and nipples as I kissed the back of her neck. My cock was now fully erect again and it brushed against her buttocks as I fondled her.
I started a slow gradual descent down the back of her body kissing her neck, shoulders and back until I knelt behind her. When I reached her buttocks I planted kisses on both ass cheeks and tickled her crack with my tongue. Sherry couldn't take anymore of my teasing so she turned her body toward me, grasped my head in both hands and pulled me against her pubes. I found her pussy with my tongue and I grabbed both of her ass cheeks as I began to lick her pussy. Sherry gasped aloud as my tongue found her clit and she held my head tightly as she experienced a mild orgasm. Her body shook and she seemed to hold onto me for balance.
I guided Sherry over to the bed and she immediately splayed her legs and welcomed me back to her pussy. I eased my dick into her pussy and began to fuck her slowly. Soon my cock was sliding easily in and out of her and we picked up the pace. Sherry wrapped her arms around my back and her legs around the back of my legs. She arched her back as she humped me hard and fast and I made sure that my cock stayed in contact with her clit as I plowed her cunt. We fucked hard and long working ourselves toward an exhaustive state. I did not want to cum as I wanted to fuck her silly. I was relieved when I felt her tense up.
"Walt, hold me, hold me, I'm coming, oh, oh, oh" Sherry said louder than she wanted as she reached her crescendo!
She tensed up wrapping her arms around my back and her legs around the back of my legs in a vice like grip. I held her trembling body tight and I could feel her drench my cock with her pussy juice. I remained still with my cock still in Sherry's pussy as she uttered unintelligent moans and sounds and her body quivered. Her vagina muscles were involuntarily squeezing and releasing my cock. My cock slipped from her vagina and she flinched as cool air touched her opening.
"Oh that was incredible. You are a very good lover, Walt," she sighed.
"Well you are too and I really enjoy you," I replied.
We rested for awhile and at this point 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. Then I grabbed some lotion and put an ample amount in her asshole. Sherry moaned and cooed as I fingered her pussy and her asshole simultaneously. I tired to get her asshole slick enough so that I could fuck her ass.
"What do you want?" she asked.
I didn't answer her but instead I 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 always found that body lotion and saliva will make my cock as slippery as possible. 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. Sherry moaned as my penis filled her hole.
I fucked her with long and deliberate strokes until my cock was sliding easily back and forth in 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. For some reason I looked at the wall and I saw a reflection in the mirror on the wall. It was Toni. She had opened my bedroom door far enough to see and she was watching me fuck Sherry in the ass. I don't know how long Toni had been watching us but I didn't care as I returned my attention to Sherry.
I caressed her big tits and tweaked her nipples as I leaned over her body and said loud enough for Toni to hear, "Sherry you have a hot ass, I love fucking you in your hot ass."
My hands freely roamed her body and I pulled on her hips drawing her backwards impaling her further on my inflated member. I reached for her pussy to finger fuck her and diddle her clit but I found Sherry's hand already buried in her cunt. She was frigging herself frantically working herself toward an orgasm. Suddenly I felt my cock inside her ass swell up and I started pumping faster. Within minutes I knew that Sherry felt the warm fluid being squirted inside her anus and she immediately started to cum herself. Her cunt walls convulsed around her own hand fucking her cunt as her anal muscles squeezed every drop from my spurting cock. I grunted as my whole body became stiff and I slammed my cock harder into her. Sherry 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. She surprised me when she covered my cock with her mouth and sucked any remaining cum from my tool. The both of us were exhausted and Sherry curled up in my arms. I looked toward the door and it was closed again. The two of us then dozed off. When I woke up in the morning Sherry was gone. She left me a note reminding me that she was headed up to Vail and thanked me for a great time together. Normally I would have loved to fuck Sherry with my morning piss hard-on but that day I was happy to sleep in.
NEXT CHAPTER
Anal sex with Beverly and Pamela.