14 Memorable Anal Encounters 05

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 asleep.

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 forcefulness 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 asleep 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.

NUMBER 2 – CHARLOTTE

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 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. 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 kids and the kids 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.