Memorable Anal Encounters

Bonnie is number three and Charlotte number two


Bonnie and I had been out several times and we did sl**p together each time. She was a great lay with a fantastic body but she had this odd behavior. She always acted reluctant toward anal and oral sex. When I came in her mouth she acted annoyed and when I fucked her ass she acted as if she didn't want to do it, but she always did it and she never once refused to suck my cock or take it in the ass. I suspected it was her way of justifying her behavior.

I met Bonnie in night school in 1975. Bonnie was a vibrant young woman with light brown hair that just covered her neck. She had a nice figure with tits that I guessed to be a 34 C but her best feature was her round shapely bubble butt. I had always been a leg and ass man, so nice tits were a bonus but not a necessity, as I favored women with shapely bottoms. She looked great totally naked and I would often stroke and play with her fabulous body until she begged me to take her to bed. Bonnie had one of the nicest asses that I had ever seen and I loved fucking her hot ass.

One Friday night she invited me over to her place. We sat on the sofa watching TV, sipping our drinks and discussing the college class. I got up to refresh my drink and when I returned I sat next to her. She turned toward me and smiled nervously as she anticipated my next move. I smiled back and put my arm around her and drew her to me. I gently pulled her toward me and our mouths locked in a kiss. I pushed my tongue into her mouth and it took her breath away. Bonnie kissed me back and her body relaxed as she welcomed the fact that she would get fucked that night. I lifted her sweater up over her head as she held her arms up for me to remove it. Next I unfastened her bra and as I removed it her tits stood straight out from her chest. I pushed her shoulders back against the sofa causing her tits to look bigger and firmer. Bonnie moaned as I leaned over and kissed her breasts and sucked on her rock hard nipples. I kissed and sucked her tits for several minutes. Her nipples got so long and so hard that they were like little dicks sticking out from her tits. She loved to have her tits fondled and kissed.

I moved off the sofa and knelt between her legs. I unzipped her skirt and she lifted her hips as I pulled it down and off her body. Bonnie looked very sexy clad only in her thigh high nylons and her robin blue panties with her aroused tits standing straight out. Hooking my fingers in the waistband of her panties I slowly peeled them down her legs. As I removed her panties I stared directly at her snatch and gently pushed her legs apart. Bonnie groaned as I ran my finger over her well trimmed pussy mound and tickled her labia. Her hips jerked involuntarily when I probed her sopping wet pussy with my finger and kissed her inner thighs. Bonnie gasped aloud when my tongue finally touched her quim.

I raised Bonnie's legs up and placed them on my shoulders which brought her pussy even closer to my mouth. Then I reached up and fondled her tits with both hands, tweaked her nipples and plunged my tongue into the depths of her pussy. I licked her cunt and located her erect clit with my tongue. As I sucked on her clit and played her tits and nipples, Bonnie moaned loudly as her body thrashed around. I struggled to keep my mouth glued to her pussy as her body jumped all over the sofa. Bonnie grabbed my head with both hands and held me to her gushing pussy.

"Oh Walt, this is going to be a quick one, a big one," she cried out and then she screamed, "I'm cumming, oh God I'm cumming, hold me, hold me tight, please hold me."

Bonnie's body seemed to go through convulsions as her orgasm rocked her and sent tremors through her. She continued to hold my head to her mound as her sweet nectar gushed into my mouth. I licked her dry and nibbled on her clit which caused her body to quake again. Bonnie collapsed on the sofa so I stood up and looked down at her hot body as I peeled off my shirt. Unbuckling my belt and unzipping my pants, I pushed my trousers down to my ankles. My large erection was covered by my underwear but my state of desire was obvious. I pushed my underwear down and my cock caught in the waistband and bobbed in front of Bonnie. She stared at my erect cock as it dangled inches from her face. Bonnie stared at it as if she was looking at the first cock she had ever seen in person. I reached down and pulled her closer to me so that her mouth was now on a level with my cock.

"Your turn," I said as I pushed my cock toward her mouth.

"I don't like to suck cock," Bonnie said acting out her reluctance.

"Well make an exception this time," I replied firmly.

"Please don't make me do it," she begged.

"I'm not going to make you do it. I want you to want to do it. Just suck it for awhile until I am really hard. I won't cum in your mouth if that's what you are worried about," I told her trying convince her to suck my cock.

Then I reminded her, "After all I did eat your pussy and lick up all your love juice."

Bonnie reluctantly moved her head forward and kissed the head of my cock. Then she licked up and down the shaft and all around it. Eventually, after more urging on my part, she took about four inches of my cock into her mouth. In spite of her suspect reluctance, Bonnie was clearly an experienced cocksucker. She clearly knew her way around a cock and she seemed enamored with mine as she loved it with her mouth. As I looked at her distraught face sucking my cock I thought about my promise to not cum in her mouth.

"Yeah I won't cum in your mouth tonight but before this weekend is over you will taste it and feel my seed coat your rectum," I thought to myself.

As I lifted Bonnie's chin up and my cock slipped from her mouth she spoke, "Can we go upstairs to my bedroom?" she asked hopefully.

"I thought that you would never ask," I teased.

Bonnie led me to her bedroom and I watched her fantastic ass as she walked up the stairs in front of me. Her beautiful shapely ass undulated as she climbed the stairs and I felt that familiar surge in my loins. I wanted to throw her down right on the stairs, shove my cock all the way up her ass and fuck her until I filled her rectum with semen. But I knew better, so I watched her shapely bottom with each step she took up the stairs. I knew that I wouldn't be happy until I fucked her ass that weekend.

I followed her up the stairs and into her bedroom. Bonnie pulled down her bed covers and got in bed on her back. She spread her legs slightly and looked apprehensively at my erect cock. I got on the bed between her thighs and nestled my cock at the opening to her pussy. I moved the head of my cock around her vulva and gently prodded her outer cunt lips. Bonnie moaned softly as her pussy got increasingly wetter. Satisfied that she was wet enough I eased my dick in a little parting her labia and finding the entrance to her pussy. I pushed more of my cock into her and in spite of her wetness she was still very snug. For the next several minutes I pushed in and pulled out, each time pushing a little more of my shaft into her sopping wet hole. Finally my cock sank all the way into her snatch causing Bonnie to gasp aloud. Then as I began to saw my dick in and out of her, Bonnie wrapped her legs around my lower body and humped her hips up at me. As I picked up the pace I made sure that my cock stayed in constant contact with her clit.

Bonnie surprised herself with another quick orgasm but I kept right on fucking her and she came multiple times in succession. Her pussy was flooded with her cunt juice and I could feel my cock soaking in her nectar as I pushed it all the way in. Bonnie was experiencing a continuous string of orgasms which had her body thrashing and jerking about as they led up to her final crescendo. Her body stiffened and she grabbed my shoulders as she wrapped her legs even tighter around my torso squeezing my lower body.

"Oh God, I'm cumming again, hold me, please hold me, oh, oh, please," she cried out as a thunderous climax ripped through her body.

Bonnie stiffened at first pushing her hips toward mine and the she went out of control. Her hips humped rapidly up and down as her body thrashed about. She was grunting and groaning and gasping for air as she reached her crescendo. All her fanatic actions accelerated my own orgasm and I flooded her womb with barrage after barrage of semen. I plowed my cock into her as far as I could as I released a steady flow of spunk into her pussy. We both humped each other furiously until our orgasms subsided. I kept my weight on my elbows as I lay on top of her so as not to crush her body with my weight. Bonnie's vaginal muscles clenched and unclenched around my shaft milking my cock dry.

Her cunt was a receptacle holding our combined juices and my cock felt as if it bathing in warm oil. My cock slowly deflated and slipped from her tight pussy with an audible sound. Our juices flowed out of her pussy as soon as my cock slipped from her hole just as if a stopper was pulled out of her. I rolled to my side along side of Bonnie and flopped on my back.

"Oh my, I haven't cum like that in a while. It was a little scary," she sighed and then added.

As I lay by her side I noticed that her tits were standing straight up and her aroused nipples were pointing at the ceiling. I tweaked the hard little nubs between my fingers causing her to gasp and quiver.

"My breasts are always very sensitive," she murmured.

I leaned over and kissed her breasts and sucked on her sensitive nipples. I rubbed her firm flat tummy as I sucked on her tits and her rock hard nubs.

"Oh I love that it makes me feel so feminine," she cooed.

As I sucked her tits and continued to rub her belly, I let my hand drift down to her wet pussy. I ran my fingers through her cum soaked pubic hair and I felt my cock starting to harden. Bonnie begged me to let her rest as she was sure that she could not possibly cum again. I rolled her onto her stomach and lifted her hips to a level with my cock as I knelt behind her. I eased my cock into her pussy and began to fuck her doggy style. Bonnie was content in this position since I was not in contact with her clit. I slammed into her from behind causing her curvy ass cheeks to jiggle.

I scooped up gobs of her pussy juice and smeared it in the crack of her ass spreading around her nether hole. I added saliva to my finger and probed her tight aperture with the tip of my finger. She tensed when she felt my finger probe her asshole. I gathered up more juices and added more saliva as I continued to probe her hole and open her up. I gently pushed a very well lubricated finger into her ass and the tiny aperture opened up to accept the digit. More saliva and more juices greased her asshole sufficiently to allow me to slide my finger all the way into her rectum.

Bonnie thought that I was preparing her ass for my cock when she said, "Please don't. I don't like anal sex."

"Don't worry," I assured her, "I will just play with your ass as I fuck you."

Now with my cock in her pussy and my finger in her ass I was approaching another orgasm. I could it building in my balls, travel through my scrotum and splash the insides of her vagina with my warm semen. As I came in her pussy I thought to myself yet again, "Just wait until you feel my warm seed fill your ass tomorrow night."

On Saturday morning I woke up first with a piss hard-on. This happened frequently to me when I spent the night with a hot woman. With this piss hard-on I was able to fuck for quite awhile without cumming and until the bladder pressure got so intense that I had to relieve myself. I rolled over toward Bonnie and started caressing her body. She rolled on her back and I went to work on her firm tits and hard nipples. She cooed from the titillation and gradually woke up. Then I moved between her legs and slid my erect dick in her pussy.

The fit was tight again so I moved slowly and gently working my cock into her. Bonnie got wet quickly and my cock was soon sliding in and out of her hot cunt. As she had done before she wrapped her legs around my lower body and her arms around my back as she humped back at me. I fucked her through multiple orgasms just as I had done last night except that I didn't cum. Bonnie arched her back and her body shook with the intensity of her climax. I kept fucking her and she had another continuous string of orgasms before her body stopped moving of its own accord.

"Please stop, let me rest, I can't cum anymore," Bonnie cried out, "Walt please stop, please."

I stopped fucking her honoring her plea and I slowly slid my still erect cock from her. I headed into the bathroom to relieve the pressure of my piss hard-on and then I opted to take a shower. Bonnie joined me in the bathroom once she heard the shower running. I invited her to join me in the shower. Bonnie and I soaped each other's body and I loved running my soapy hands all over her fantastic tits and ass. Bonnie played with my erect cock and lathered it up with soap. I turned her toward the shower wall and slid my cock into her pussy from behind. Bonnie braced herself against the shower wall as I fucked her pussy until I came shooting another good sized load into her.

We finished showering and Bonnie douched all the semen from her body. Afterwards we got dressed and went out for breakfast and spent the day together. That evening we had dinner at the Wine Cellar her favorite restaurant. As we drove back to her condo Bonnie was very amorous as the wine had an obvious effect on her. When we arrived we went straight to her bedroom, undressed and got in her bed. I moved Bonnie into a 69 position and ate her until she came. Once again she came quickly and thrust her pussy at me as I ate her dry. She sucked my cock without my urging this time but I still did not cum in her mouth.

I rolled Bonnie on her back and slid between her legs. My cock slid in easily this time and I fucked her silly before finally shooting my load in her pussy. Bonnie really came hard again as the orgasm ripped through her body. She was a very sensuous woman. We lay together and I played with her tits and nipples and worked them into a state of arousal. Bonnie cooed as I worked on her tits, rubbed her tummy and played with her soaked pussy.

Once again I got hard from the foreplay and rolled her over on all fours. Bonnie agreeably moved into the doggy position and accepted my cock in her pussy. As I fucked her slowly I rubbed her tits and played with her asshole. I easily inserted one finger in her ass and then with my other hand I diddled her clit as I fucked her from behind, Bonnie went wild again with all the stimulation and she began bucking her hips as her orgasm took over her body. As she was bucking I slipped my cock out of her pussy and quickly pushed it in her ass. Bonnie bucked and humped through her orgasm before she reacted to my cock in her ass.

Bonnie put on her reluctant act, "No please not that. Take it out. You know I don't want to do this. Please take it out!"

But I didn't take it out and I ignored her pleas as I pushed more of my cock into her ass. I added more saliva and pussy juice as I fucked her and shoved more cock into her ass. Bonnie tried to break loose but I held her hips firmly. Another push and my entire cock went all the way in her ass. Her asshole opened up from the reaming and I was then able to slide my cock in and out with ease. I was convinced at that moment that she had been butt fucked before. I marveled at her shapely hot ass as I watched her impaled on my cock.

"Walt please don't, I don't want to do this. Please don't cum in me," Bonnie acted again but not as urgently this time.

Once again I ignored her pleas and I picked up the pace. I could feel my own orgasm approaching and I knew it would be a big one since I was so turned on fucking Bonnie's beautiful ass. Her ass had loosened up and my cock was sliding easily in and out of her rectum. My hips slammed into hers and her ass jiggled as my cock went balls deep into her asshole. I felt my balls tighten so I pushed my cock all the way in her ass and then I released torrents of semen into her rectum. Stream after stream of semen filled her asshole as I flooded her bowels with my load.

I realized that we were both motionless and I had my cock buried all the way up her ass. Then I began to fuck her ass slowly again and I pushed my copious load around in her rectum. As I withdrew my softening cock from her ass, gobs of spunk trickled out and ran down over her pussy lips and inner thighs. Bonnie flopped facedown on the bed and I knelt there watching my seed ooze out of her shapely ass.

"Why did you do that to me? You know I didn't want that. I told you that I don't like anal sex," she whimpered.

I thought to myself, get used to it but I said, "You always say that but you know that I can't resist your ass. It is so beautiful, so hot, so inviting."

"I don't want you to ever do it again. I don't like it," she said as she always would.

I had knew that she had been butt fucked before me since my cock went in fairly easy with the right amount of lube and she did not complain of any pain. Bonnie got out of bed and went into the bathroom to clean up. When she returned we cuddled in the spoon position and we fell asl**p without any more conversation. I woke up at about 3:00 AM with a piss hard-on but this time I went to bathroom and relived myself. While in the bathroom I located some lotion and I put an ample amount on my cock before returning to bed. When I got back in bed I snuggled up to Bonnie and slipped my lotion covered cock into her ass. I had both hands around her body so I played with her tits and fingered her pussy as I slowly fucked her ass. Bonnie woke up and quickly realized that I was back in her ass. "Oh not again, please no," she whispered.
I just kept fucking her until I came in her ass again. Ropes of semen shot into her ass and I felt the involuntary clutching and un-clutching of her anal muscles around my cock. Her sphincter muscle milked my cock dry as it tried to expel the intruder. My cock softened and slipped from her ass emitting a grunt from Bonnie when it did. I held her to me and we both eventually fell back asl**p.

Sunday morning was a repeat of Saturday morning as I fucked Bonnie through countless orgasms until she begged me to stop. Then we fucked in the shower again and I came in her pussy. We went out for breakfast and then to the park for a long walk. Later we ate at a casual restaurant. After dinner we drove back to Bonnie's house and as before we immediately went up to her bedroom. As we had done last night we got into a 69 position on our sides. I ate Bonnie's pussy and fingered her asshole again as she sucked my cock. Bonnie assumed that this was our normal foreplay in preparation for our fuck session but I surprised her when I came in her mouth.

I was particularly turned on and I had been thinking about cumming in her mouth all day. It didn't take long after we were in the 69 position that I shot a rope of cum in her mouth. Bonnie jerked her head back in surprise and the second shot hit her on her face. Bonnie put her hand over my cock head to block the shots but a third one hit her face before she could block anymore. Bonnie spit out as much as she could of the first shot that filled her mouth but I knew she could still taste it.

"Why did you cum in my mouth? You promised me that you wouldn't. It is so humiliating!" she said faking her reluctance one again.

"Oh stop your acting. I swallow your pussy juice all the time. A little cum isn't going to hurt you," I replied sternly and then added, "I didn't promise you tonight that I wouldn't cum in your mouth. I was pretty turned on and you were doing a good job sucking my cock and I just lost it."

"Well you could have warned me that you were about to cum," she snapped.

"Yes I could have but I decided not to as I wanted to cum in your mouth just as I wanted to cum in your ass," I replied sharply.

Bonnie knew that I was on to her act. I resumed eating Bonnie's pussy and fingering her ass and much to my surprise she put my cock back in her mouth. Bonnie drank the remaining cum from my cock and sucked me until I was hard again. She had a number of orgasms as I ate her pussy. Now that I was hard again it was time to take her ass.

There was no trickery or f***efulness this time as I had her get on all fours. I got the lotion from the bathroom and applied an ample amount to my cock and her asshole. I sawed my fingers in and out of her ass and pussy as I prepared her for another ass reaming. Bonnie cooed with the dual action of fingers in her ass and pussy but I could tell she was still reluctant to be butt fucked. I knelt closer to her and placed my cock at the entrance to her asshole and pushed ever so slightly. I watched as her little rosebud opened up to accept my rod and the cock head cleared her sphincter.

Bonnie had her head down on the bed turned to one side and she grasped the bed covers with both hands. I slowly fucked her ass trying to make this session last as long as possible. I loved watching my cock slide in and out of her beautiful shapely ass. As hard as I tried to prolong her butt fucking I felt my orgasm building rapidly. I thrust into her plunging my cock in all the way and released my seed into her bowels. Rope after rope shot out of my cock to fill her ass with my warm semen. Bonnie was fucking me back and I realized that her hand had traveled to her pussy and she was getting herself off as I flooded her ass with my spunk.

The two of us collapsed on the bed with me on top of her and my cock still buried in her ass. I could feel her ass muscles milking my cock as her buttocks contracted and relaxed under me. I pushed up on my elbows to keep my weight off her but I kept my hips in contact with her shapely ass until my cock softened and slipped out. We both fell asl**p and never stirred again.

Bonnie and I continued our affair for almost a year. I knew she was dating other guys but she surprised me on night when she told me that she had become engaged to get married. Of course she waited until after our marathon of sex before telling me and showing me her ring. Then she said that it had to be our last night together. I agreed and we fucked once more that evening before I left. I never did see Bonnie after that.


I selected Charlotte as my second favorite not because she had a great ass but because she loved anal sex. The other thing I loved about Charlotte was that when she was in the mood it didn't make any difference where we were, in someone's house, in a public place or in my car.

Charlotte, although she preferred to be called Charlie was one of the corporate groupies at our company. This story takes place in 1971, a year when everyone was sexually promiscuous and condoms were rarely used. There was a bar that all of us hung out at called the Oasis which also sponsored one of the softball teams I played on. I also played for another bar and our company team. All three teams had many of the same ballplayers and we actually did very well in our leagues and in tournaments. Softball tournaments were huge in the Midwest back then and we were in at least two a month. It was at a softball tournament that I first hooked up with Charlotte. Charlie was a 28 year old brunette with brown eyes, about 5'5" and 120 pounds. She was not the prettiest of girls but she wasn't ugly either. Charlie had served in the Army before she worked at our company so she was no virgin and no stranger to brief encounters.

We had won our first two games in a 16 team double elimination tournament and we had the whole afternoon off. We were not scheduled to play again until 8:00 PM that evening in the third round of the winner's bracket. My friend Al had his girlfriend Ginger at the game. Ginger was good friends with Charlie who had accompanied Ginger to the game. Al invited me to join him and Ginger at her house for lunch and a few pops between games. Ginger introduced me to Charlie and she confirmed Al's invitation.

When we arrived at Ginger's house her first words were that we all had to take showers before we used the beds. I was surprised but not shocked at her announcement. I knew Al was banging Ginger on a regular basis so it was not a surprise that the two of them would jump in the sack.

Charlie just smiled at me and said, "Come on I'll show you where the guest shower and bedroom are that is unless you'd rather watch TV."

"Lead the way," I replied not wanting to pass up an opportunity for some afternoon delights.

Charlie and I stripped down and entered the shower. She had a large birth mark on her shoulder that she was embarrassed about but I quickly put her at ease. I started to soap up her tits, ass and pussy but she stopped me.

"Let's save that for the bedroom. Ginger doesn't like it when the shower runs too long," she told me.

Charlie had obviously done this before at Ginger's place and I followed her advice. We washed ourselves quickly and then went into the bedroom. Charlie lay on the bed and opened her legs for me. She held up her arms and welcomed me into her body.

"I had been hoping that we would get a chance to make it together someday," she whispered.

Slowly, I moved into her. Charlie 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.

"Charlie," I groaned, "You are really tight."

She moaned in response, "Your big 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 f***e of our fierce, a****listic 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. Not wanting to crush her I rolled off her as my cock deflated and slipped from her cum filled cunt. We rested together as we talked for awhile. Charlie knew that I was fucking a few girls from the office and she had told Ginger that she would like to make it with me, which is why Ginger invited her to the tournament. I learned that Charlie had been married but was divorced in the Army. She also told me that she was not at all into oral sex either giving or receiving. Charlie reached down and stroked my cock as we talked and I fondled her tits and played with her pussy. Before long we were turned on again.

I pulled her legs apart and let her guide my cock into her pussy. I eased my thick cock into Charlie's tight cunt and worked it slowly until I was balls deep in her pussy. I knew that with her tightness that she could probably feel every ridge and vein of my cock touch her vaginal wall. Charlie gasped again when I hit bottom. As I fucked her slowly I made sure that my cock never lost contact with her clit. Charlie 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. Charlie stiffened one more time, screamed and then went limp with her final orgasm which was the most intense of the day.

Once again I rolled off Charlie and this time she rolled over on her stomach. I caressed her ass and teased her between her ass cheeks. I searched for her nether hole as I massaged her bottom. I finally reached the object of my desire and I rubbed juice from her pussy into her asshole. 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. 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 scooped more juice out of her pussy with my fingers and pushed it into her asshole. Charlie's hips bucked in response to my probing. I loved anal sex and I loved to watch my cock slide in and out of a hot ass. I was hoping that Charlie was into anal sex. As my finger entered her channel she gripped it with her sphincter muscle. I continued to finger fuck her ass adding more natural lube from her pussy as needed and eventually I added a second finger. Satisfied that she was well lubed I straddled her hips and guided 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 and pushed back obviously wanting more.

"Not too deep at first and then go deeper," she whispered.

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 slippery hole. I continued my slow penetration until the entire length of my shaft was balls deep in her ass. Charlie gasped and grabbed the bed sheets as I hit bottom and then 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 still 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 as I fucked her ass and played with her tits. Charlie 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 was so snug that I wondered how the semen ever got out of my cock. I fought to hold back my ejaculation 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," she sighed as my cock remained nestled in her hole.

Charlie told me that she loved anal sex and that sometimes she actually preferred it to vaginal sex. She said that she still wanted to cum and she preferred a cock shooting a load in her ass while her clit was being rubbed. 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. Charlie rolled toward me and smiled as she whispered.

"That was some great sex today, you are a good lover," she said softly and then, "Come on it's time to get up and get dressed."

Charlie and I showered quickly and dressed. She told me that she first had anal sex in the Army and over time she had become addicted to it. Charlie told me that she liked anal sex as much as vaginal sex and sometimes even more with the right person. When we went into the kitchen Ginger had already put out some snacks for us. The four of us ate and then we returned to the tournament. We won our third game and the next day we would be playing in the winner's bracket championship.

On Sunday we lost the first game and we had to play the team coming out of the loser's bracket. We beat them and then we had to beat the same team twice to win the tournament. We won the first game but then they came back and beat us in the championship game. It was tough playing four games back to back but that's what can happen in double elimination tournaments. All and all it was a good tournament for us. I was pretty tired as was the rest of our team so we passed on drinks at the Oasis and headed home. Tomorrow was a work day.

I didn't see Charlie again until Friday that same week. Terry a girl who worked in corporate and her current squeeze Russ had a party at Terry's house. Terry was divorced with a couple of k**s and the k**s were spending the night at her parent's house. I went solo to the party since I wasn't really dating anyone.

Another friend and ball player, Manny was supposed to meet Charlie at the party but he showed up with a last minute date named Cindy. Charlie was miffed but she kept her cool but by the time Manny had arrived just about everyone had paired off. I had my sights set on a cute thin blonde named Susan. I was drawn to her more by her outfit at first. She looked very stylish and she wore a cap that made her looked very British. I expected an English accent when I spoke to her but I learned that she too worked in corporate and she was originally from Kentucky.

Charlie approached me and asked if she could speak with me just for a minute. I excused my self from Susan to speak with Charlie. "Can you meet me down stairs in a few seconds?" she asked.

I told her I would but I noticed that she had been drinking heavy. I went down the stairs a few moments after her and she ushered me into the bathroom on the lower level. Charlie closed and locked the door, turned her back to me and pulled down her shorts. She was not wearing any panties under her shorts. It was a new style outfit with a halter top and the matching tops and bottoms were held in place by elastic. Charlie had elected not to wear panties under her bottoms and as I found out shortly she passed on the bra too.

"I need you to fuck my ass before you head out with Susan," Charlie requested slurring her words a little.

I dropped my pants and underwear and I pushed my fingers in Charlie's pussy. I moved my fingers from her pussy to her asshole for several minutes gathering her pussy juice and lubing her asshole. Then I pushed my cock in her pussy and got it good and wet before I eased it into her ass. Charlie grunted as my cock hit home and slid into her ass. We both fucked rapidly as I pushed her top up over her tits and played with her tits and nipples. I reached with one hand for her pussy and plunged two then three fingers into her quim. Charlie went wild with the double penetration and the manipulation of her tits. She soaked my fingers with her female juice as she had a string of orgasms.

Then I felt my seed shoot through my cock into the depths of her ass causing Charlie to groan loudly. She milked my cock dry with her talented sphincter muscle and her hips thrashed uncontrollably ejecting my cock from her ass. I held her tightly and my wet cock brushed against her creamy ass cheeks.

"Oh thank you, thank you," she cooed as her body calmed.

I washed my cock off in the sink and then dressed and returned to the party. Charlie stayed in the bathroom longer after I left and I did not see her leave. It was ironic that Charlie and I had hooked up twice in other people's homes. I was talking with Susan again when Charlie left and not long after that Susan invited me to her apartment. Susan was my twelfth favorite described in an early story.

It was a few weeks before Charlie and I hooked up again and it was quite by accident. I had worked late one night and I stopped off at the Oasis for a night cap. It was a slow night and I was the only one in the bar until Charlie came in. She had been out bar hopping and hadn't found anything to her liking so she decided to swing by the Oasis on the way home. She had not eaten dinner so I suggested that we grab a snack and a drink together.

Charlie and I sat side by side at a bar table facing the bar. The bartender Dan was engrossed in the TV watching a ball game and getting caught up on all the scores. As we ate our burgers and sipped our beers, I ran my hands over Charlie's nylon covered thighs. She was wearing pantyhose under her red mini dress but no panties. I slid my hand between Charlie's thighs and covered her hose protected pussy. I rubbed her cunt through the hose and her pussy got sopping wet. We finished our burgers and beers and then left the Oasis. When we got out to the parking lot I asked Charlie if she wanted to sit in my car for awhile.

"You better believe it, as worked up as you got me in there you better take care of me," she replied excitedly.

Charlie and I got in the back seat of my two-door Grand Am and I immediately peeled off her panty hose. I lowered my pants and underwear to my knees and the two of us played with each other for several minutes. The Grand Am had louvered rear windows so it was impossible for anyone outside the car to see in the back seat. There was something very erotic about being partially clothed but still having access to each other. Charlie had her legs spread wide as I fingered her pussy and pushed her cunt juice into her ass. Charlie stroked my cock with her hand as I prepared her for another ass fuck.
I never knew anyone like Charlie who could get so wet during foreplay. My hand was sopping wet and within minutes I had her asshole coated with her own pussy juice. I positioned Charlie so that she was kneeling down on the back seat and I knelt behind her. I put my cock in her pussy and let it soak in her juices before I lined it up with her ass.

Once again Charlie reminded me, "Not too deep at first and then deeper."

I eased my cock into her asshole as she maneuvered her body to accommodate the anal penetration. Charlie had her head down on the car seat turned to one side and I watched her face grimace slightly as my cock made its way into her ass. Charlie moaned and groaned as I slowly fucked her going a little deeper in her ass with each thrust. Once I was all the way in I picked up the pace and fucked her until I flooded her ass with my cum. Charlie had her fingers buried in her twat and she brought herself off as I plowed her ass. When my hips stopped moving Charlie milked my cock with her anal muscle and then her hips gyrated as her own orgasm overtook her. I had to hold her tightly to keep my cock in her ass as her hips jerked out of control.

My cock softened and I eased it out of Charlie's ass. I knelt there looking at her recently violated asshole and watched as my semen trickled out of her rectum. Charlie remained still for a few minutes with her red dress thrown up over her back and her ass on display. I had some paper napkins in the car and she used them to wipe the semen from her ass before she sat down on the car seat.

"You definitely have the largest cock that has ever been in my ass. Do you know how big it is?" Charlie asked.

"Well Karen measured it one time when she was blowing me and she said it was almost 8 inches long and just over 5 inches around," I replied.

"It certainly felt bigger than that tonight," Charlie sighed.

"At times I do feel thicker and longer but I have never thought about my size very much," I admitted and added, "I know that there are plenty of cocks bigger than mine."

"I think tonight was one of those nights that you peaked and your cock is plenty big for me," she said with a giggle.

Charlie did not bother putting on her pantyhose when I pulled up my pants. I opened the car door and we got out of the back seat. Charlie said that she was glad that she ran into me and that she would see me later, then she said goodnight and made her way over to her car. I watched as she got in her car and as she did her skirt flew up and flashed her bare pussy. After she left the parking lot, I drove home in a very sated state.

It was at least another week before Charlie and I met up again. It was a repeat performance with me stripping off her pantyhose in the back seat of my car, lubricating her ass with her own juices and fucking her tight ass. It was exciting for me to strip off her hose and fondle her legs, pussy and ass. Charlotte seemed to like being without her panties and hose in the back seat of the car. I took my time with her, fingering her pussy and ass driving her crazy, until she finally begged me to fuck her in the ass.

The final time it was another night at the Oasis and Charlie had had too much to drink. I put her in one of the booths toward the back to let her sl**p it off and I told her girl friend Ginger that I would take her home later. Ginger and Al were anxious to get going that night and they didn't want to wait for Charlie to wake up. They thanked me and left and I joined Dan at the bar for a night cap. I didn't drink too much since I was driving and after a while I decided to take Charlie home. I picked her up and carried her out to my car all the while I hoped that she wouldn't get sick. I placed Charlie in the front seat and buckled her in. Charlie woke up and told me that she was staying at her s****r's pad that night. She managed to stay awake and give me directions to her s****r's place.

Once we arrived at her s****r's, I helped Charlie into the house and the guest room. It was late and I assumed that her s****r was asl**p in the other room. Charlie flopped down on the bed and I then had the urge to fuck her before I left. I moved over to the bed and stripped Charlie naked. I removed her blouse and bra, her shorts and panties and her shoes. Then I stripped down naked and got in bed with her. It was the first time that we were totally naked again since the very first time we had sex.

I rolled Charlie to her side and she knew what was coming next. I scoop her female juice from her pussy and used it to lubricate her asshole. Charlie cooed as my fingers probed her pussy and lubed her ass. Then I placed my cock in her pussy just for few strokes to get it slick. I positioned my cock at her ass and gently pushed my cock into her.

"Not too deep at first and then deeper," Charlie whispered those familiar instructions.

I did what she asked and as I fucked her ass I went a little deeper each time. Soon I was balls deep in her ass and I picked up the pace. My cock felt longer and thicker than I could remember at that moment. I reached around Charlie with my left hand and played with her tits and rock hard nipples. Then I moved my right hand to her pussy and pushed three fingers into her cunt. Charlie was going wild and she was creaming all over my fingers as I plowed her ass. My cock was throbbing in her asshole and I felt my pending ejaculation building in my balls. One more deep thrust and I held my cock there as I exploded in her ass. My cock pulsated as streams of cum shot into her ass. Charlie instinctively clenched and unclenched my cock with her anal muscles. She milked every drop of cum from my cock.

For some reason I stayed hard that night and I kept right on fucking Charlie's ass. I knew it would be a while before I came again so I pulled out of her ass and rolled her on her back. Then I pushed my raging hard cock in her pussy and treated her to an exhilarating fuck. I kept my cock in constant contact with her clit and I had Charlie writhing and trembling as a continuous string of orgasms rocked her body. Then I pulled my cock out of her pussy and rolled her back to her side and re-entered her ass. I pummeled her ass as I sought out my second orgasm of the night. Charlie's ass was loose and slippery from our combined juices but she was still snug enough around my cock. Once again I stiffened and fired a barrage of cum into her rectum. I could feel my cock pulsate again as it released a torrent of cum 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 Charlie's asshole.

"I wish you could stay with me tonight," Charlie whispered.

"Not tonight Charlie, I have to be up early in the morning. Plus I don't think you want your s****r to find us in her guest bed in the morning either," I replied.

Charlie just nodded her agreement and then I got up to get dressed. I dressed and left the house quietly and then drove home. It was the last time that I had sex with Charlie. Our company was going through some downsizing and Charlie was one of the casualties. She ended up taking a job with another company and she stopped hanging around the Oasis and her former co-workers. I still think back to our five anal encounters, two in my car and three in other people's homes. It was wild.

100% (7/0)
Categories: AnalFirst TimeMature
Posted by fotisampini
11 months ago    Views: 683
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