14 Memorable Anal Encounters 02

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.

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