14 Memorable Anal Encounters 02
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 11 -- TERRI
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.
NUMBER 10 -- RITA
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.
"Are you going to join me or just watch?" she asked teasingly.
I smiled back at her and I undressed as she watched. I removed my three piece suit, shirt, tie, shoes and socks. When I got to my boxers I purposely allowed the waistband to catch my cock as I lowered them. My erect cock jumped out as the boxers released it and I smiled at Rita's reaction.
"You know Ohio has laws against carrying a concealed weapon," she said as she subconsciously licked her lips.
"Well it isn't concealed now is it?" I replied.
"No, it isn't," she responded with a chuckle.
She retrieved a tube of lubricant and tossed it to me. Then she got on the bed on all fours. Looking over her shoulder she smiled and spoke softly.
"Put plenty of that stuff in my ass and on your cock. I need to be well greased to take that ass buster of yours," clearly stating what she wanted.
I moved toward the bed and climbed on it behind her. I massaged her shapely ass cheeks and molded the firm flesh in my hands. Rita shivered in anticipation and goose bumps appeared on her buttocks and thighs. I squirted the lube directly on her nether hole and pushed it in with my index finger, moving it around until my finger was gliding in and out easily. Before adding a second finger I put more lube in her ass and then inserted my middle finger along with my index finger. She cooed as she accepted the two finger penetration and stimulation. As I fingered her ass with two fingers I slipped my ring finger and little finger in her pussy. I sawed the four fingers in and out of her asshole and pussy until she begged for my cock.
"Stop teasing me and get that big cock in my ass," she gasped.
I put gobs of lube on my cock and then added my saliva making it as slippery as possible. Rita lowered her head to the bed and turned it to one side as I began my journey into her ass. I pushed my hips forward as I held onto her hips and my cock bumped up against her sphincter. Rita gasped and placed her hand on my thigh as if to control the penetration. Another push and my cock head was in her ass.
She was holding her breath as I inched more and more of my cock into her anal passage. I told her to relax and breathe as I slowly fed my cock to her a little at a time. I eased it in, stopped, withdrew a little and then pushed some more in. I took my time and I was careful not to hurt her as I filled her shapely ass with my raging shaft.
"Oh sweet mother of God, I have never been so full. Go easy but put it all in. I want your whole cock in me," she cried out.
I pushed once more and the final inch of my cock disappeared into her asshole. I remained still for a moment and allowed her to adjust to the girth of my cock and then I began to fuck her ever so slowly. She eventually began to move her hips in an attempt to match my thrusts but it was obvious that she had been stretched to new dimensions.
She was gasping and grunting as I began to pummel her ass. When I reached for her pussy I found her hand already in place frigging herself frantically. I picked up the pace and held to Rita's shapely buttocks as our hips slapped noisily together. She was really into it now and the two of us fucked like maniacs.
"Oh yeah that's it, that's the way to fuck my ass. Give it to me, cum in me, cum in my ass," she screamed.
We were both sweating from the physical intensity of our butt fucking. I slammed into her as my cock now moved freely in her ass. I felt my orgasm approaching and as much as I wanted to prolong the ass fucking session, I couldn't. My body stiffened and I plunged my cock all the way into her gorgeous ass. Streams of semen shot into her rectum as I seemed to cum continuously for several minutes.
"Oh good, I feel it. Fill me up, fill up my ass," she cried out and then her own orgasm hit her, "Oh shit, here it is, I'm cumming!"
Her body thrashed around as I held onto her curvy ass cheeks and kept my cock buried in her ass. Her fingers flew over her pussy and clit as my warm seed flooded her anal passage. She then collapsed face down on the bed and my cock slipped from her ass with an audible pop. I knelt over her as my cock dripped the remaining cum on her curvy ass. She wiggled her bottom and squealed in delight.
"I have to admit it Walt that I have never been ass fucked like that. You are one hell of a butt fucker," she said and then rolled onto her back and looked at my semi hard cum dripping cock.
"Do you like to eat pussy?" she asked with a tone of hope.
I moved my head between her legs to eat her pussy but first I kissed and licked around the area and her inner thighs. I breathed warm air right on her snatch and she grabbed my head and pulled it to her cunt. I pulled my head back off her pussy and let my fingers trail to her pussy. I lightly rubbed her outer cunt lips and she twitched with each touch. She moaned as her clit responded to the stimulation and slowly exited its hood looking for attention.
I placed my fingers on her cunt lips and trapped her clit between them and it became engorged and stood erect. She squirmed in pleasure while I moved her cunt lips up and down on her clit and she shuddered from the extreme arousal. Still moving her cunt lips up and down, I bent down and kissed her clit. She jerked and bucked as my lips touched her upright nub. I drew my head back a bit and again blew air directly onto her clit as she writhed and bucked again, moaning with pleasure.
I placed my arms behind her knees and raised her hips up. I put her legs over my shoulders and I lowered my mouth to her pussy and kissed it as though it were her mouth. She groaned with delight as she waited for my next advance. I drew my tongue along her outer labia, up one side and down the other without touching her clit.
"Suck it please, please lick it, oh please!" she moaned lustfully.
I flicked my tongue across the edges of her pussy as she quivered and seeped her juices from between the lips. I licked the juices from the edges telling her she tasted delicious. She was nearly mad with desire as she begged me to pleasure her with my tongue. I parted her labia with my tongue and licked the insides of her cunt lips, nibbling each one a little and then sucking on them both. She whimpered and moaned when I suddenly plunged my tongue as deep as I could into her pussy. She screamed with delight as my tongue explored the insides of her pussy. Instinctively, she grasped my head and pulled it into her cunt, begging me to lick and suck her. I did not disappoint her as I swirled my tongue around her engorged clit and back into her sopping wet cunt. She was constantly moaning as my lips closed about her clit and sucked her clit in and out of my mouth. Writhing and gyrating she exploded in another powerful orgasm, drenching my face and mouth with her copious juices. She seemed to cum with each spasm of her body. I did not let up sucking her clit and she tried to push my face away as she cried out.
"Oh stop, please stop. I can't cum anymore let me rest," she begged.
Her body shuddered through yet again another orgasm and she lay there gasping and breathing heavy as her orgasm abated. Finally her orgasm subsided and she embraced me and kissed me. I knew that she could taste her own juices on my lips and I plunged my tongue into her mouth taking her breath away.
"That was marvelous, absolutely incredible. You are quite the lover," she sighed.
By now my cock was rock hard again and I moved between her legs. I eased my cock into her sopping wet pussy and she wrapped her legs around my torso.
"Is there no end to this?" she asked playfully.
"Not just yet anyway," I replied and I began to fuck her gently.
Slowly, I moved into her. Rita opened beneath me, enveloping my penis tightly. Her cunt was like a fist as she clenched her vaginal muscles. She squeezed me as I moved within her.
"Rita," I groaned, "You are really tight."
She moaned in response, "Your cock feels so good. Fill me up with it."
I thrust into her deeply and I felt the head of my cock pressing against her cervix.
"Oh Walt," she sighed with her eyes closed.
I felt her vagina contract around my cock. She climaxed again with a shudder and a long moan and she urged me on, "Fuck me baby. I can take it, I want it."
I grabbed her hips in my hands and began to thrust in and out as I pounded her pussy. My heavy bloated testicles slapped against her ass as my cock drove into her hot pussy.
"Yes, oh yes," she gasped as her body rose to meet me.
The bed was now rocking with the force of our fierce, animalistic fucking. Her legs clamped around my waist as she screamed her release. Her pussy grasped my cock, squeezing it and milking it as I fucked her. I moved my hips against hers and buried my cock to the hilt within her. Her quaking pussy erupted into orgasm again as I rocked my cock slowly, grinding the head against her cervix. I felt my orgasm building in my balls and I knew that any second I would be spewing my seed into her womb. I felt my semen travel from my scrotum through my cock as I came deep inside her flooding her waiting warmth with my load.
Neither one of us could speak as the pleasure was so intense. I collapsed on her and she wrapped her arms and legs even tighter around my body. I kissed her neck and she sighed aloud then I kissed her on the lips and our tongues dueled with each others briefly. Not wanting to crush her I rolled off her as my cock deflated and slipped from her cum filled cunt.
"Between my ass and my pussy I feel as if a fire hose was turned on me," she sighed.
"I need a shower. Want to join me?" she suggested.
I agreed as we were both dripping wet with perspiration from the intensity of our love making. The night had turned out better than I could have hoped it would. Rita and I showered and washed each other's body. I loved soaping up her tits and raising her hard nipples. She was fascinated with my cock and seemed to enjoy handling it and cupping my big balls. After the shower I offered her a massage. She handed me a bottle of massage oil and got back in bed on her back.
"Do my front first," she said sexily.
She closed her eyes as I gently placed the fragrant oil on my hands and with two fingers on each hand I made small gentle circles over her forehead. I then moved to her cheeks, massaged her nose and her lips, and her chin, then back to her temples and down the side of her face and neck. Leaning over her I slipped my oily hands over her breasts. She smiled at me and I bent my head and kissed her gently. She reached up and took my hands and pressed them to her breasts as her hardened nipples pushed against my palms. I held the bottle of warm oil above her breast and a single drop splashed on her nipple and ran down her side and she flinched with the sensation and giggled at the action. I smiled back at her and poured a small trail of oil down her stomach and then I began massaging her breasts, one in each hand as I looked into her eyes.
She glanced upwards again to watch as my hands moved down to her ribs and chest and stomach, spreading the oil until she was glistening in the dim light of the room. I knew she loved the feeling as my hands moved over her breasts, chest, and stomach. She looked at my crotch and saw that my cock was fully aroused and sticking straight up. She smiled as she reached and gently grasped my cock in her tiny hand. I let out a small moan as she moved her hand up and down my huge shaft. She took some oil from me and placed some on the head of my cock then and she placed her palm over the top, gently squeezing and releasing the pressure on my shaft.
She spread the oil over my cock as she continued to stroke me squeezing her hand around the shaft as she felt my hand move over her pubic hair. I moved my hand downward until my hand covered her entire moist area. Rita spread her legs as my middle finger probed the folds of her labia. Gently I inserted my finger sliding it in effortlessly within her warm channel. Rita began stroking me in rhythm to my finger entering and withdrawing in her pussy.
I was afraid that I would cum if she continued to work my cock in her oily hand so I removed my finger from her pussy and massaged her thighs. I put plenty of oil on her luscious thighs and rubbed it in thoroughly. Her quad muscles relaxed under my movements and she emitted an audible sigh. I worked her inner thighs and massaged them all the way from her knee to her pussy letting the back of my hands brush against her pubic mound. Her engorged clitoris peeked out of her pussy lips and I trapped it between two of my oily fingers. Rita jumped at the contact and once again she reached for my cock.
"Make love to me again," she whispered.
I pulled her legs apart and let her guide my cock into her pussy. I eased my thick cock into Rita's tight cunt and worked it slowly until I was balls deep in her pussy. I knew that she had never been so full until that night and that she could probably feel every ridge and vein of my cock touch her vaginal wall. Rita gasped again when I hit bottom. As I fucked her slowly I made sure that my cock never lost contact with her clit. Rita stiffened as she orgasmed and then grunted and groaned through multiple orgasms as her body was rocked with one climax after the other. As I pounded her pussy my cock moved easily in her now soaked pussy. Rita stiffened one more time, screamed and then went limp with her final orgasm which was the most intense of the night. The two of us were drained, sweaty and oily as we slowly recovered from our intense fuck session.
"My God I will never be the same after today," she gasped.
"You bring out the best in me," I teased.
"I need to rest for awhile," she said as she rolled over on her stomach.
I'll do your back now and finish the massage," I offered.
Rita just sighed so I oiled up my hands, straddled her body and went to work on her shoulders. She cooed as I rubbed the tension out of her upper body. I worked my way down from Rita's shoulders to her trap muscles and lower back. I massaged her back just above her buttocks and she continued to coo and moan with pleasure. I bypassed her ass for the moment and went to her calves. I massaged each calf and worked my way up to the back of her thighs. As I massaged the back of her legs and thighs my eyes were fixed on her marvelous ass.
I finally reached the object of my desire and I rubbed plenty of oil onto Rita's buttocks. She lifted her hips slightly as I worked her firm ass cheeks. I pulled her buns apart slightly and stared at the cute little aperture. It was hard to believe that earlier my thick cock had been buried in that tiny hole. I leaned over and ran my tongue over her nether hole causing her to gasp in surprise. I suspected that no one had ever rimmed her before and she moaned again as my tongue probed the target. I traced my finger over the ridges of her now swollen sphincter and watched as it seemed to pulse and throb under its own accord.
I took the bottle of oil and placed it right on her nether hole and let a few drops fall on it. I pushed the oil in her asshole and her hips bucked in response. As my finger entered her channel she gripped it with her anal muscles. I continued to finger fuck her ass adding more oil as needed and eventually adding a second finger. Satisfied that she was well oiled I straddled her hips and guided my slick cock into her ass. My cock head slipped past the oily 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 and pushed back obviously wanting more.
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 slid easily in her oily hole. I continued my slow penetration until the entire length of my shaft was balls deep in her ass. Rita gasped and grabbed the bed sheets as I hit bottom and then moved her ass in time with my thrusts. I felt my balls tighten just before I came again. There was not much semen but the sensation was just as pleasurable for me. I collapsed on her body and then rolled her to the spoon position with my cock still embedded in her ass.
We remained in the spoon position for quite awhile. I think we even dozed and we were awakened when my deflated cock slipped from her ass. Rita rolled toward me and smiled as she whispered.
"Kiss me," she said softly.
I wrapped my arms around her and we embraced and kissed. We stayed on our sides facing one another kissing and talking for several minutes. Then she shocked me with her next statement.
"I can't let you stay the night. The guy I'm living with will be home in the early morning," she told me.
I checked the time and saw that I still had two hours to get out of there so I took another shower, dressed and left. Rita was already asleep when I got out of the shower so I left quietly so as not to disturb her. I never ran into or heard from Rita again. I assumed that she was horny that one night and hoped to get lucky. As it turned out we both got lucky. She was a good fuck and loved anal as I did.
NUMBER 9 -- BARBARA
It was 1983 and the software company I worked for decided to have the user conference in Chicago. I was the Western Region Manager based in the Chicago area and I had responsibility for everything west of the Mississippi River. Barbara the corporate administrator in charge of conference logistics came to Chicago to select the hotel for the conference. She had received several bids from large hotels in the city and she would visit each one while she was in town. She had asked me where to stay and I told her the Westin which used to be the Continental Plaza. The Westin had offered her a complimentary room since she was in charge of booking the conference.
Barb arrived on Monday evening and checked in at the Westin. On Tuesday she planned to visit two of the five hotels under consideration. On Wednesday she would visit the other three and then on Thursday she would select one, sign the contract and fly back to Philadelphia. Barb asked me to have dinner with her on Wednesday evening.
It was business as usual for me on Monday, Tuesday and Wednesday. On Wednesday afternoon I went into the city and met Barb at the hotel. She wanted to go to a nice restaurant that had a good bar. I took her to Sweetwater's and she loved the place. We had a couple of drinks before dinner and then we had a great meal. Barb got a little tipsy as she drank the wine especially after a couple of cocktails. She got very talkative and shared some things about her life with me.
Barb was 36 years old and she was a pleasing looking blonde. One would not say she was pretty but one would admit that she was alluring. She stood at 5'6" and probably weighed no more than 125 pounds. She had nice legs and incredible ass with small breasts. Her ass was her best asset as it stuck out slightly and seemed to beckon to be touched.
Barb was married to her current husband for 10 years. She told me that she was sexually active outside her marriage but that she never really had an affair. It was mostly one night stands and it was when she was on the road on company business. She told me that she had a number of encounters with hotel staff and that they would often hand her their business card and offer their services to her. I wondered why she shared this part of her life with me but then I was to find out later that night more about her.
I steered the conversation back to the hotel selection for the user conference. Barbara told me how she had the hotels ranked in order of preference and she had selected the Westin as her first choice. I agreed with her on that choice not only because it was a five star hotel but because of its location. It was right off the magnificent mile that was filled with top of the line stores and shops. It was only a few blocks from Oak Street Beach and one block from the Water Tower Place. The theater district and nightlife were short cab rides from the hotel. There would be plenty to do for the spouses that accompanied their partners to the conference. Barbara was glad that I agreed with her selection and supported her choice.
We had finished our dinner and the wine so I asked her if she would like an after dinner drink, coffee and dessert. Barbara passed and suggested that we have the after dinner drink in her room at the Westin. We took a taxi back to the hotel and went up to her room. They had given her a suite with a well stocked mini bar and everything was complimentary.
"Let's get undressed and then have that drink," Barb said catching me off guard.
"You want us to get us undressed?" I questioned in confirmation.
"Sure, why not? Our clothes are going to come off soon anyway," she replied with a smile.
I was all for it as I was anxious to get a look at her naked and check out her curvy ass. I undressed as she did and we watched each other at the same time. Barb smiled when my underwear came off and she saw my cock in its flaccid state hanging between my legs. I anxiously waited until she turned her back to me so that I could see her naked ass. Barb turned to put her clothes on the chair and I was treated to a view of her amazing ass. It was perfectly shaped seemed to reach out toward me. I secretly hoped that she liked anal sex.
"I'll have a Baileys," she told me.
I got a Baileys for her and a cognac for me and then we reclined in the bed together. We clicked glasses in a toast and sipped our after dinner drinks.
"You know I don't usually do this. I mean that I don't sleep with company employees," Barb admitted.
"I don't either," I lied.
"So we can make an exception this time but I need your promise to be discreet," she stated.
"You have my word. I do not tell tales out of school. Our sex lives should be our own business," I assured her.
"Good I am glad that you agree," she said and then took another sip of her drink.
Barb put her drink down on the nightstand, smiled at me and reached for my cock. "You have a nice cock," she told me just before she slid down and took it in her mouth.
I leaned back as her very skilled mouth got me hard within minutes. I put my drink down and put my hands in her silky blonde hair as her head bobbed up and down. Satisfied that I was sufficiently hard, Barb mounted me and lowered her dripping wet pussy onto my cock. She looked me right in the eye as she started to ride me and I knew that she was in desperate need of an orgasm. I reached up and played with her small tits and tweaked her hard nipples as she rode me. Barb's was breathing hard and rapid as she approached her release. I looked into her eyes and I could see the lust in them. Then it happened.
"Oh God, oh God, oh, oh, hold me," she screamed as an orgasm of a massive proportion rocked her body.
She rode through her orgasm and I felt my cock swimming in her pussy. Barb then collapsed on my chest for several minutes until she composed herself. She then lifted her self off my cock and I heard a distinct sucking sound as my cock was released from her pussy. Barb reached for my cock, wrapped one hand around its girth and looked up at me with those daring blue eyes. She then tilted her head back down and brought her mouth towards my cock. She ran her tongue up its smooth underbelly and I groaned aloud.
Holding it with her hand she sank her open mouth down onto my cock. Her lips closed around it and I felt her hot, wet tongue go to work. She sucked me hard and her cheeks hollowed as she worked her head back and forth. I gasped and put my fingers into her soft blonde hair to guide her head back and forth. Barb knew what she was doing as her pace slowly quickened and her right hand worked my shaft. Her left hand cradled my balls and softly stroked them. She then ran her finger along my perineum. Barb took my cock from her mouth and blew on the head of it. I felt her breath cool the saliva on my cock and I clenched my butt in pleasure. My large cock bulged in her firm grip and felt even larger than normal. Barb worked her hand back and forth letting it glide smoothly around my cock then she looked up at me and smiled. She knew the effect she was having on me and she seemed to enjoy every moment of my torment.
I moaned again as her tongue snaked forward and tickled the tip of my cock. Her tongue found the pee hole and she licked the pre-cum as it oozed out of my slit. She worked her tongue in circles around the tip of my cock and took my length deeply into her mouth again. I watched as almost the full length of my cock vanished into her mouth. Barb then swirled her tongue around the shaft of my cock that was buried in her mouth. I closed my eyes and groaned in pleasure as her head worked back and forth more quickly clasping my shaft with both hands as her head vigorously bobbed up and down.
Her pace was relentless and I held her head gently as I felt my orgasm building in my testicles. This was definitely the best blow job I'd ever had in my life, bar none. Barb allowed my cock to plop out of her mouth again and a thin trail of saliva stretched from my cock to her lips. She smiled again and caught the saliva in her hand as her eyes fixed on my cock. Her hand wrapped tightly around it again and she proceeded to jerk me off me at a steady pace occasionally licking the head of my cock and nibbling it with her teeth. I threw my head back. Closed my eyes and groaned out loud. Barb jerked me off as fast as she could as her hand almost became a blur as it moved up and down my shaft. There was a distinct look of lust in her eyes as she stared at my cock
"Are you going to cum for me? Are you close?" she asked in a raspy voice.
I just nodded yes since I was very close. Barb then took me back in her mouth and ran her tongue around my shaft again. Then her head bobbed up and down again as she pursed her lips and hallowed her cheeks. That did it for me.
"Barb here it cums," I warned and then I grunted as I came in her mouth.
Barb took my warning as a signal and she started sucking harder and squeezing my cock with her hand. My eyes closed tight as I ejaculated in her mouth. I felt my cock pulsate as rope after rope of semen shot into her mouth. As the intense sensations passed from my body I relaxed a little and looked down to watch Barb suck every drop from my cock. She was now kissing it, licking up and down the shaft as if she were making love to it. My cock softened in her mouth and she took it in her hand as she licked the final remnants of my ejaculation from the slit. Once she was satisfied that she had emptied my cock she ran her tongue around her kips and swallowed one final time. Barb let out a big sigh and sat up on the bed.
We rested for several minutes, sipped our after dinner drinks and chatted easily. Then we began playing with each other again and when I found Barb's G-spot she came again. She held my hand tight to her pussy as she humped it vigorously. Then she stiffened and screamed as another orgasm rocked her.
"No one has ever found that spot as quickly as you did," she gasped and then requested, "Fuck me doggy style this time."
She rolled over on all fours, put her head down on the bed and raised her curvy ass in the air. I wanted to just drive my cock in her ass but I knew it would be better for her to warm up to it. I still didn't know if she liked anal sex. I knelt behind Barb and slipped my cock into her pussy from behind. I fucked her slowly and then I began to play with her ass. I caressed the shapely globes and teased her anus with my finger. I scooped up some of her pussy juice and rubbed it into her anus. Barb wiggled her ass in response so I took it to the next step. I pulled my cock out of her pussy and ran it up and down the crack of her ass. Then I paused at her nether hole and prodded it gently with my rigid cock.
"Oh, where's the Vaseline?" Barb cooed.
I knew then she was going to let me have her ass. I hopped out of bed and dashed to the bathroom and quickly located the body lotion supplied by the hotel. Then I got back in bed behind Barb and thoroughly coated her anus with the lotion. I put gobs of lotion on my cock and then added my saliva to it. My cock was as slick as oil and I eased it into her ass. My cock slid in like a hot knife through butter and I buried it to the hilt in her ass.
Barb emitted a gasp as my cock slid all the way in on the first thrust. I plowed her asshole and fucked her rapidly in search of my much needed orgasm. She eventually began to move her hips in an attempt to match my thrusts and it was obvious that she was turned on by the anal sex. Barb was gasping and grunting as I began to really pummel her ass. I picked up the pace even more and held to Barb's shapely buttocks as our hips slapped noisily together. She was really into it now and the two of us fucked like maniacs.
"Oh yeah that's it, that's the way to fuck my ass. Give it to me, cum in me, cum in my ass," she screamed.
We were both sweating from the physical intensity of our butt fucking. I slammed into her as my cock now moved freely in her ass. I felt my orgasm approaching and as much as I wanted to prolong the ass fucking session, I couldn't. My body stiffened and I plunged my cock all the way into her gorgeous ass. Streams of semen shot into her rectum as I seemed to cum continuously for several minutes.
"Oh good, I feel it. Fill me up, fill up my ass," she cried out and then her own orgasm hit her, "Oh shit, here it is, I'm cumming!"
Her body thrashed around as I held onto her curvy ass cheeks and kept my cock buried in her ass. Her fingers flew over her pussy and clit as my warm seed flooded her anal passage. She then collapsed face down on the bed and my cock slipped from her ass with an audible pop. I knelt over her as my cock dripped the remaining cum on her curvy ass. She wiggled her bottom and squealed in delight. I moved back from Barb and I admired her shapely ass. She looked so sexy that I rubbed her buttocks lovingly and she clenched her ass muscles. She then rolled over on her back and spread her legs for me.
"You made me so hot come here and eat my pussy," she pleaded.
I climbed on the bed and moved my head between her legs to eat her pussy but first I kissed and licked around the area and her inner thighs. I breathed warm air right on her snatch and she grabbed my head and pulled it to her cunt. I pulled my head back off her pussy and let my fingers trail to her pussy. I lightly rubbed her outer cunt lips and she twitched with each touch. She moaned as her clit responded to the stimulation and slowly exited its hood looking for attention.
I placed my fingers on her cunt lips and trapped her clit between them and it became engorged and stood erect. She squirmed in pleasure while I moved her cunt lips up and down on her clit and she shuddered from the extreme arousal. Still moving her cunt lips up and down, I bent down and kissed her clit. She jerked and bucked as my lips touched her upright nub. I drew my head back a bit and again blew air directly onto her clit as she writhed and bucked again, moaning with pleasure.
I placed my arms behind her knees and raised her hips up. I put her legs over my shoulders and I lowered my mouth to her pussy and kissed it as though it were her mouth. She groaned with delight as she waited for my next advance. I drew my tongue along her outer labia, up one side and down the other without touching her clit.
"Suck it please, please lick it, oh please!" she moaned lustfully.
I flicked my tongue across the edges of her pussy as she quivered and seeped her juices from between the lips. I licked the juices from the edges telling her she tasted delicious. She was nearly mad with desire as she begged me to pleasure her with my tongue. I parted her labia with my tongue and licked the insides of her cunt lips, nibbling each one a little and then sucking on them both. She whimpered and moaned when I suddenly plunged my tongue as deep as I could into her pussy. She screamed with delight as my tongue explored the insides of her pussy. Instinctively, she grasped my head and pulled it into her cunt, begging me to lick and suck her. I did not disappoint her as I swirled my tongue around her engorged clit and back into her sopping wet cunt. She was constantly moaning as my lips closed about her clit and sucked her clit in and out of my mouth. Writhing and gyrating she exploded in another powerful orgasm, drenching my face and mouth with her copious juices. She seemed to cum with each spasm of her body. I did not let up sucking her clit and she tried to push my face away as she cried out.
"Oh stop, please stop. I can't cum anymore let me rest," she begged.
Her body shuddered through yet again another orgasm and she lay there gasping and breathing heavy as her orgasm abated. Finally her orgasm subsided and she embraced me and kissed me. I knew that she could taste her own juices on my lips and I plunged my tongue into her mouth taking her breath away. By now my cock was rock hard again and I moved between her legs. I eased my cock into her sopping wet pussy and she wrapped her legs around my torso.
"My, we are horny this evening aren't we?" she asked playfully.
"I'm always horny for you," I replied and I began to fuck her gently.
Slowly, I moved into her. Barb opened beneath me, enveloping my penis tightly. Her cunt was like a fist as she clenched her vaginal muscles. She squeezed me as I moved within her.
She moaned in response, "Your cock feels so good. Fill me up with it."
I thrust into her deeply and I felt the head of my cock pressing against her cervix.
"Oh Walt," she sighed with her eyes closed.
I felt her vagina contract around my cock. She climaxed again with a shudder and a long moan and she urged me on, "Fuck me, I want it so much."
I grabbed her hips in my hands and began to thrust in and out as I pounded her pussy. My heavy bloated testicles slapped against her ass as my cock drove into her hot pussy.
"Yes, oh yes," she gasped as her body rose to meet me.
The bed was now rocking with the force of our fierce, animalistic fucking. Her legs clamped around my waist as she screamed her release. Her pussy grasped my cock, squeezing it and milking it as I fucked her. I moved my hips against hers and buried my cock to the hilt within her. Her quaking pussy erupted into orgasm again as I rocked my cock slowly, grinding the head against her cervix. I felt my orgasm building in my balls and I knew that any second I would be spewing my seed into her womb. I felt my semen travel from my scrotum through my cock as I came deep inside her flooding her waiting warmth with my load.
Neither one of us could speak as the pleasure was so intense. I collapsed on her and she wrapped her arms and legs even tighter around my body. I kissed her neck and she sighed aloud then I kissed her on the lips and our tongues dueled with each others briefly. Not wanting to crush her I rolled off her as my cock deflated and slipped from her cum filled cunt.
"Stay with in me in my bed tonight," Barb suggested.
I woke up Thursday morning lying on my side next to Barb who was also on her side. She was cuddled up in a spoon position with her bottom pushed into my crotch and my morning piss hard-on was tucked between the cheeks of her ass. I reached around and cupped Barb's small firm tits with my hands. Then with one hand I trailed it down her body and found her pussy. I inserted a finger into her quim and diddled her clit until she rolled to her back. Her pussy was soaking wet again as I mounted her and slid my cock into her. Barb just moaned with her eyes closed as I began the ritual of fucking her with my morning hard-on. I fucked her through multiple orgasms as I had done in the past until she begged me to stop and let her rest. I pulled out of her and went into the bathroom with my erect cock pointing the way.
"Come back to bed after you go to the bathroom," she told me.
I relieved myself and then returned to bed as she had asked. Barb had me lie on my back as she positioned her head near my cock. She then proceeded to give me one of her fantastic blow jobs. I was very turned on and I knew that I would blow my load quickly particularly with Barb's skill at oral sex.
"Let me know when you are going to cum," she said and then returned to sucking my cock.
I felt my orgasm building from my toes to my cock and I let Barb know that I was really close. She took my cock from her mouth and stroked it with her hand. Her pace quickened as my cock seemed to get harder and bigger. Then with her other hand she cupped my bloated balls and fingered my perineum. That did it and my body stiffened as cum shot out of my cock. Barb kept jerking me off as she watched rope after rope of semen shoot out of my cock and land on my chest and stomach. She kept working my cock until the remaining seed was just oozing from my cock head and trickling into my pubic hair.
Barb then sucked the remaining cum from cock, licked off her hand and smacked her lips. "I wanted to watch when you cum," she said almost pleased with herself.
"I'll call room service for breakfast and then you can have my ass again if you're up to it. After we eat we can get to work today," Barb said as she swung her shapely legs out of bed.
She ordered room service and as promised let me have her ass again. We showered, dressed, ate breakfast at the Westin and then I headed home to change clothes before I went to the office. Barb met with the Westin staff, signed the contract and then flew back to New Jersey. It was set that next year's user conference would be held in Chicago in May. I looked forward to her return to Chicago. Actually as it turned out, Barb and I hooked up several times on my visits to the home office before the user conference and again while she was in Chicago. We were both very discreet and enjoyed our special relationship. I will always remember her sweet ass.
NEXT CHAPTER
More anal action with Peggy, Lee and Sherry.