14 Memorable Anal Encounters 02

"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.