INTRODUCTION
I have always been a big fan of anal sex. Probably for two reasons, the first being that I feel it is the ultimate submission when a girl gives up her ass. The second reason however is that it is the most erotic scene and sensation to have a woman on all fours as I watch my cock slide in and out between her lovely cheeks. I just love it when she has her head turned to the side with a dreamy expression on her face as her ass is filled with my cock.
Over the years, I have had sex with many women and most of them were very good lovers. I had anal sex with twelve of them but it was the anal sex in a vehicle that was among the most memorable. That happened with four women; Charlotte was more than once so it was multiple encounters. I won't say one was better than the other because each situation was different. So, I will tell this story in chronological order. I have written about these women in other stories submitted to Literotica but this is the first grouping about anal sex in the car.
I had other sex in cars mostly oral and a number of vaginal sex encounters. However, although very satisfying and enjoyable, they were not nearly as erotic and exciting as anal sex in the car. In almost every instance we remained partially clothed.
CHARLOTTE
It was 1970 and I was a 29-year-old fit guy at 6'1" and 190 pounds. I had light brown hair and hazel eyes that the girls loved. In addition to my daily gym workouts, I loved to snow ski and play tennis. I was also a SCUBA diver and loved diving in the Caribbean. I was working in the information systems division of a Midwest manufacturing company.
I met Charlotte at a party one night and we hit it off. She was not a beautiful girl, in fact she had kind of a mousy appearance. Her body however was something to behold. She was 35 at the time and she had a shapely 36-28-35 figure, brown curly hair and brown eyes. The first night we were together I learned that she did not do oral but that she loved anal. I fucked her pussy thoroughly bringing her a lot of pleasure before I came in her. Afterward I began playing with her ass and she admitted that she liked anal sex.
That first night I came in her ass twice and she loved it. We hooked up two more times over the span off a couple of months and had anal sex on each occasion. I liked her in the doggy position. Her favorite was the spoon position with my cock in her ass, my fingers in her pussy and my other hand groping her tits. I was seeing other girls at the same time so it was not a steady thing with Charlotte and me.
We hooked up again one night and it was quite by accident. I had worked late one night and I stopped off at the pub, a local hangout, for a night cap. It was a slow night and I was the only one in the bar until she came in. She had been out bar hopping and hadn't found anything to her liking so she decided to swing by the pub on the way home. She had not eaten dinner so I suggested that we grab a snack and a drink together.
We sat side by side at a bar table facing the bar. The bartender Dan, an addicted gambler, 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 her nylon covered thighs. She was wearing pantyhose under her red mini dress but no panties. She always wore panty hose as opposed to regular nylons. I slid my hand between her 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 pub. When we got out to the parking lot I asked her if she wanted to sit in my car as I felt she was ready to fuck.
I drove to a remote spot in the parking lot and we got in the back seat of my two-door sports car. 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 car 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. She had her legs spread wide as I fingered her pussy and pushed her cunt juice into her ass. She stroked my cock with her hand as I prepared her for another ass fuck.
I never knew anyone like who could get so wet during foreplay. My hand was sopping wet and within minutes I had her anus coated with her own pussy juice. She reminded me again had she preferred anal sex to any other. I positioned her 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.
She reminded me as she always did, "Not too deep at first and then deeper."
I eased my cock into her ass as she maneuvered her body to accommodate the anal penetration. She 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. She 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. She had her fingers buried in her twat and she brought herself off as I plowed her ass. When my hips stopped moving she milked my cock with her sphincter 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. She 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.
She 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. She 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 ass. After she left the parking lot, I drove home in a very sated state.
It was at least another week before we 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. That night I wanted to play with her tits so I unzipped the back of her dress and unhooked her bra.
As I fucked her ass the top of her dress was down to her waist and her tits hung down beneath the loosened bra. I leaned over her and grasped her breast with both hands as I drilled her bottom. She was frigging her pussy and within minutes we were both cumming. Once again, I shot a massive load in her ass and she milked my cock dry. As before I handed her napkins to clean up and we redressed before she headed for her own car.
The final time it was another evening at the pub and we were anxious to get at each other. We got in the back seat again and I pulled off her hose. She said she wanted to try to spoon in the car so we stretched out on the back seat the best we could. I unzipped her dress and unhooked her bra as I had the last time. I scooped her female juice from her pussy and used it to lubricate her anus. In all the times, we had anal sex we had only used her juices as natural lube. She 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," she again 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 her 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. She was going wild and she was creaming all over my fingers as I plowed her ass. My cock was throbbing in her ass 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. She instinctively clenched and unclenched my cock with her sphincter. She milked every drop of cum from my cock.
I stayed hard that night and I kept right on fucking her ass. I knew it would be a while before I came again. body. I pummeled her ass as I sought out my second orgasm of the night. Her 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 her anus. We were both breathing hard from the exhilarating anal sex. I finally retrieved the paper napkins and handed them to her. We both moved gingerly and redressed ourselves.
That was our last sex in the car and we only got together one more time. I had taken a job with another company and left town. During the time I had seen Charlotte we had anal sex ten times but the three times in the car were by far the most exciting.
MAUREEN
It was 1978 the third year in my new job when I met Maureen. She was a very different looking young woman as she was as tall as me at 6'1" but she was slender and fit. Her breasts were very small, just little mounds on her chest. There wasn't much curve to her body but she had one thing most tall girls don't have and that was a great ass. It was perfectly shaped, round and protruding. She would not normally be the type of woman I would try to bed but that ass had my attention.
I had been sleeping with a number of women since moving to the town in 1976. I only had two anal encounters but they were both rewarding. I bagged a co-worker Beth twice in the ass after taking good care of her needs. The other was a one night stand with a nurse that I met in a bar late one night. The other women I had slept with were all decent lovers and one of them we stayed together for nearly a year.
It was after a going away party that Maureen or Mo, as she preferred to be called, and I hooked up. She had worn tight slacks that day and I could not take my eyes off of her ass all night. I struck up a conversation with her and she was receptive to my advances. Just before we planned to leave the bar together, she stopped in the ladies' room. A colleague of mine came up to me and whispered that Mo had a reputation of giving great head. I didn't know about getting a blow job but I was definitely interested in the ass.
When she returned from the bathroom, I invited her to my place but she had a different suggestion. She was driving her roommate's van that night and she asked me to sit in it with her. She drove to a remote end of the parking lot with no cars around and then we got in back. She wasted no time in getting to her knees in front of me to free my cock. With her deft experienced hands, she had my pants unzipped, unfastened and pushed down to my knees along with my underwear. My cock was already hard with she took it in my mouth.
Her reputation was well earned as she was an excellent cock sucker. All the while she remained clothed as she sucked my cock, occasionally testing her gag line as she tried several times to deep throat me. I reached over her and fondled her ass through the tight slacks and she got the hint that I wanted to fuck her. She pulled off my cock and she shed her slacks and panties. I followed suit and took off my pants and underwear. We were both naked from the waist down.
From there we stretched out on our side in a 69 position. She obviously wanted to suck my cock and I wasn't going to deny her that. I buried my face in her pussy and she loved it. As we ate each other, I fondled her lovely ass. I tickled her tailbone which sent shivers through her body. I toyed with her nether hole and tested the tightness of the taut rubbery ring. Wetting a finger in her pussy, I began moving her juices to her anus.
I managed to get my middle finger all the way in to her snug hole and she didn't protest. Suddenly she exploded and drench my face with her love juices. I held tightly to her curvy firm buttocks as she bucked and groaned as she climaxed. Her body began to recover and I rolled her to her back. Moving between her legs, I slipped my cock in her pussy and fucked her through another orgasm. She begged me to let her rest but I was far from done with her.
Mo agreeably moved into the doggy position and accepted my cock back in her pussy. As I fucked her slowly I played with her anus. I easily inserted one finger in her ass and then with my other hand I diddled her clit as I fucked her from behind. Getting my fingers wet in her pussy, I was able to add a second finger into her bottom. It was snug bit she did not protest. Satisfied that she was wet and loose enough, I slipped my cock out of her pussy and quickly pushed it in her ass. She reacted to my cock in her ass and her body tensed up.
I pushed more of my cock into her ass. I added more saliva and pussy juice as I fucked her and shoved more into her ass. Another push and my entire cock went all the way in her ass. Her anus 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.
I was incredibly turned on and I could feel my own orgasm approaching. I knew it would be a big one since I was so excited to be fucking her beautiful ass. It 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 bottom. 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 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. Mo flopped face down on the floor of the van and I knelt there watching my seed ooze out of her shapely ass.
I knew then that she had been butt fucked before me since my cock went in fairly easy with the right amount of natural lube and she did not complain of any pain. I stroked my cock back to hardness as I stared at her magnificent ass. I snuggled up to her and slipped my cock back into her ass. I knelt closer to her and placed my cock at the entrance and pushed ever so slightly. I watched as her little rosebud opened up to accept my rod and the cock head cleared her sphincter.
She had her head down on the van floor turned to one side. I slowly fucked her ass and I knew that I would be in her for a longer time before I came the second time. I loved watching my cock slide in and out of her beautiful shapely ass. It seemed like an hour before I came again. 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. Mo 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 second load.
The two of us collapsed on the van floor with me on top of her and my cock still buried in her ass. I could feel her 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. I rolled to my back and let out a loud sigh. She remained on her belly for several minutes before she spoke.
"There is a towel in the sport bag on the back seat, get it for me."
I retrieved the towel as she asked and I watched as she wiped my seed from her bottom. She looked at me as I put my pants and underwear back on.
"Please don't tell anyone that you fucked me in the ass."
"I won't. I never talk about my affairs."
"I guessed that but I wanted to be sure."
We finished dressing and moved back up front. She drove me to my car which at that point was one of a few left in the lot. We said goodnight and I drove home feeling very fortunate to have fucked an absolutely fabulous ass. Mo and I hooked up several times after that but never in a vehicle again. I loved fucking her ass and she was always open to it as long as she got to suck my cock first. In 1979, I took another job and moved to the Chicago area.
BARBARA
By the year 1984 I had worked for this company for five years since moving to Chicago. The company was headquartered in Philadelphia and I worked in the regional office. Once again, I was fortunate with the ladies and hit it off with a number of them. I managed to have anal sex with a couple of them but never in a vehicle. It wasn't until I met Barb in the home office that I had anal car sex again.
She and I had hooked up on my first visit to the home office and then on every visit after that. She was a good lover who gave great head and gushed when I fucked her through multiple orgasms. Best of all was that she also liked anal sex but was very selective about with who she did it. We had dinner one night together and when I drove her home she had me parked away from her condo. She told me her husband was home but she still wanted to have sex before she left me.
We started playing with each other and she had my cock out of my pants in no time. I managed to open her blouse and unhook her bra so I could fondle her small tits while she sucked me. My pants and boxers were all the way down to my ankles and I reached under her skirt and rubbed her pussy. She was getting hotter and hotter. We had never had sex in the car before but I knew she was up for it that night.
"All this playing with your cock has got me hot again. I need to sit on your dick," she whispered.
I sat back on the car seat as she removed her panties, straddled my body and lowered herself onto my cock. She held my shaft and aimed it at her vagina. My hard cock slid easily into her womb and she emitted a small gasp as it filled her hole. Barb rocked back and forth on top of me as I held on to her curvy ass. I stroked her beautiful ass cheeks and molded her firm buttocks in my hands as she picked up the pace fucking herself with my dick. She started moaning as she fucked faster and faster. I leaned in and sucked on her tits and nipples as she rode my cock.
"Sweet Jesus, I love being this full of cock. Fuck me nice and slow."
I let my fingers dip down to her pussy and scooped up some of her juice. Then I teased her nether hole with a pussy moistened fingertip. She never objected to my playing with her ass and anus so I pushed my finger in a little deeper. She was going wild riding my cock and I felt my own release building in my balls. I sensed her pending orgasm and then she buried her face in my shoulder to stifle her screams just as my ejaculation flooded her womb. She stopped moving as jet after jet shot into her from my pulsating cock.
"I am going to explode. Oh, oh hold me, please hold me tight."
She collapsed on top of me her body quivering from the intensity of her orgasm. Her face in my shoulder as she screamed in passion. I could feel her juices coating my cock as it remained buried in her womb. It took a few minutes for her to regain her composure and she just sat on me and cooed. Eventually she moved off of me and sat next to me. She had had two mind blowing orgasms and she was sexually satisfied. However, I was not done with her. As always, she had not objected to the ass play so I was determined to try and fuck her fantastic ass.
Barb noticed that I was stroking my semi-hard cock and she smiled at me just before she lowered her mouth to my shaft. Within minutes she had me rock hard proving that she was an accomplished cock sucker. I was anxious to get at her ass all the while wondering if she would let me fuck her in the ass in the car. I moved her to all fours on the car seat so that she was facing the steering wheel. With her ass elevated and she placed her head on the car seat turned to one side. I started playing with her pussy and her curvy ass lubricating her with her own cunt juice. She moaned and cooed as I fingered her pussy and her ass simultaneously. I tried to get her anus wet enough with her juices and my saliva so that I could fuck her ass.
I knelt behind her and tried to insert my cock in her ass but it just wouldn't go. Afraid of hurting her I tried more pussy juice and saliva for lubrication but to no avail. There are times when my cock feels bigger and thicker and this was one of those times. I was fingering her ass when she spoke.
"Wait let me get some cream."
She reached down and got some lotion from her purse and then she handed it to me. I realized then that she was going to let me fuck her in the ass in the car. I put an ample of amount of lotion in her coating the tiny puckered opening of her anus and lubricating the rim. I added my saliva to my lotion covered cock making it super slick and nestled my dick against the entrance momentarily before easing it inside her ass. I could feel my cock struggle to stretch the resistant muscles. My dick head burrowed in and her rigid passageway soon yielded to the determined action of my cock. Barb moaned as my pecker filled her hole.
"Go slowly at first, no one has been there since your last visit."
I fucked her with long and deliberate strokes until my cock was sliding easily in and out of her ass. I caressed her shapely buttocks as I watched my dick move in and out of her rectum worming around inside of her curvy ass. I caressed her tiny firm tits and tweaked her eraser hard nipples as I leaned over her body and whispered in her ear, "Barbara, I love fucking you in your hot ass."
My hands freely roamed over her body and I pulled her by her hips drawing her backwards impaling her on my bloated cock. I reached for her pussy to finger fuck her and diddle her clit but I found her hand already buried in her womb. She was frigging herself frantically working herself toward an orgasm. Suddenly I felt my cock swell up inside her ass and I started pumping faster. Within minutes I knew that she felt the warm fluid being squirted inside her rectum and she immediately started to cum herself. Her cunt walls convulsed around her own hand fucking as her ass squeezed every drop from my spurting cock. I grunted as my whole body became stiff and I slammed my cock harder into her. She writhed around and her body arched off the car seat as a climax of massive proportion tore through her loins.
My cock slipped from her ass with an audible pop and I moved back against the car door. I caressed her shapely ass and she rotated it in circles displaying her delight. Barb then said that she really needed to get going and I checked the time. We had been fucking in her car for over two hours and it was almost midnight. We both got redressed and then we kissed good night. I drove to her condo and waited until she was safely inside before I drove away and headed back to the hotel.
That was the only time that we ever had anal sex in the car and it was fabulous. We got together every time I came to Philadelphia and we always had anal sex at least once on each visit but never in the car again. I often wondered how many people had sex in a rental car. I was sure that not many had anal sex but it was an interesting thought.
CATHLEEN
I changed jobs again in 1985 but remained in the Chicago area. I had accepted an executive position with a company and I had inherited the administrative assistant from the previous executive. Cathleen was an interesting person and to look at her not one you would expect that I would have an affair with. However, after one year we were insatiable together, not because of her looks but because she was the best lover I ever had.
She did it all. She gave great head, was a good fuck and she loved anal sex with me. At 5'5' she was a fit woman with small tits but a curvy body. She wasn't very pretty but not sore to the eye either. Her hair was strawberry blonde with a course texture. Her legs were solid and toned from all her hours of aerobics. Then there was her ass and what an ass it was. It was a work of art and perfectly shaped.
Once our affair started we had sex whenever and wherever we wanted. In my condo, at the office, in my car, at a romantic interlude. There wasn't a work day that went by that my cock wasn't in her mouth or pussy or ass. Some days it was all three. She was married, so weekends did not work and that was just as well as I could use the rest. Cathleen liked the spoon position and that was usually reserved for sex in the car. She liked having my cock in her ass while I fingered her pussy and played with her tits. I never forgot the first time we had anal sex in my car.
One night after aerobic class, we went to our favorite spot for a couple of drinks. After a few drinks we adjourned to my car so that she could suck me off. As she was blowing me she pushed her spandex down to her knees baring her ass and pussy. I played with her ass and fingered her pussy as she sucked on my cock.
"I wish you could fuck me in the ass tonight."
I asked her if she had any lotion and she dug it out of her purse. I reclined the passenger seat all the way until it was almost flat and had her lay on her left side. I prepared her ass with the lotion. I pushed my trousers and shorts down past my knees, lubed up my cock and got behind her on my side. It was tight quarters but I managed to get my cock into her ass and started banging her hard. She pushed back at me as hard as I pounded her. Soon we were both sweating and breathing hard. We made quite a sight if someone should happen to look in the car window but we were past caring about that as we raced toward our mutual orgasms. Eventually the windows fogged up and no one could see inside although they might see the car rocking. As soon as my spunk filled her ass her body went into spasm with her own orgasm soaking my fingers. I lay next to her until we recovered.
"Do you think you can go again?"
"I think so, it will take me longer to cum."
"I know. I want you in my ass all night. Let's get in the back seat."
With the car windows fogged, we crawled over the front seats into the back. I couldn't help but run my hands over her lovely ass as she moved in back. I joined her and she went right for my cock taking it in her mouth. Cathleen always kept herself squeaky clean and always douched her ass before anal sex. That's why she wasn't ever concerned about taking my cock from her ass to her mouth. She had her legs spread wide as I fingered her pussy and pushed the lotion into her ass. She sucked my cock and stroked it with her hand as I prepared her for another ass fuck. I positioned her so that she was kneeling down on the back seat and I knelt behind her. I put my cock in her pussy first and played with her ass. I loved her in this position and her ass was just so luscious.
I eased my cock into her asshole as she maneuvered her body to accommodate the anal penetration. She had her head down on the car seat turned to one side and I watched her face break into a smile as my cock made its way into her ass. She reached between my legs and fondled my balls. 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 with a passion. She wanted me in her ass all night and I wanted to stay in it forever.
She had her fingers from one hand buried in her pussy and she continued to squeeze my testicles gently with the other. She had another orgasm and I felt her gripping clenching rectum around my shaft. She could seemingly cum all night and she continued to masturbate as I fucked her ass. Eventually I could not hold out any longer and I drove deep in her as I released my second load in her bottom. I leaned over her kneeling form and when my hips stopped moving she milked my cock with her sphincter. I remained in her allowing my cock to soften but before it slipped out, her hips gyrated as another orgasm overtook her. I tried unsuccessfully to keep my cock in her ass as her hips jerked out of control.
I knelt there looking at her recently violated ass and watched as my semen trickled out of her rectum. She remained still for a few minutes with her ass on display. I got my handkerchief from my pants pocket and handed it to her. She used it to wipe the semen from her anus before she sat down on the car seat.
"Wow!" she sighed.
"Wow, indeed," I countered.
We got dressed and waited until my car windows defogged before she went to her own car. I waited until she was in her car and left the lot before I drove home. I didn't remember ever feeling so sexually sated and drained. It had been an incredible experience to fuck her ass in the car.
I again changed jobs and this time went to New York in 1990. Cathleen was my last anal lover in a vehicle but I would always remember that one night in the car.
I have always been a big fan of anal sex. Probably for two reasons, the first being that I feel it is the ultimate submission when a girl gives up her ass. The second reason however is that it is the most erotic scene and sensation to have a woman on all fours as I watch my cock slide in and out between her lovely cheeks. I just love it when she has her head turned to the side with a dreamy expression on her face as her ass is filled with my cock.
Over the years, I have had sex with many women and most of them were very good lovers. I had anal sex with twelve of them but it was the anal sex in a vehicle that was among the most memorable. That happened with four women; Charlotte was more than once so it was multiple encounters. I won't say one was better than the other because each situation was different. So, I will tell this story in chronological order. I have written about these women in other stories submitted to Literotica but this is the first grouping about anal sex in the car.
I had other sex in cars mostly oral and a number of vaginal sex encounters. However, although very satisfying and enjoyable, they were not nearly as erotic and exciting as anal sex in the car. In almost every instance we remained partially clothed.
CHARLOTTE
It was 1970 and I was a 29-year-old fit guy at 6'1" and 190 pounds. I had light brown hair and hazel eyes that the girls loved. In addition to my daily gym workouts, I loved to snow ski and play tennis. I was also a SCUBA diver and loved diving in the Caribbean. I was working in the information systems division of a Midwest manufacturing company.
I met Charlotte at a party one night and we hit it off. She was not a beautiful girl, in fact she had kind of a mousy appearance. Her body however was something to behold. She was 35 at the time and she had a shapely 36-28-35 figure, brown curly hair and brown eyes. The first night we were together I learned that she did not do oral but that she loved anal. I fucked her pussy thoroughly bringing her a lot of pleasure before I came in her. Afterward I began playing with her ass and she admitted that she liked anal sex.
That first night I came in her ass twice and she loved it. We hooked up two more times over the span off a couple of months and had anal sex on each occasion. I liked her in the doggy position. Her favorite was the spoon position with my cock in her ass, my fingers in her pussy and my other hand groping her tits. I was seeing other girls at the same time so it was not a steady thing with Charlotte and me.
We hooked up again one night and it was quite by accident. I had worked late one night and I stopped off at the pub, a local hangout, for a night cap. It was a slow night and I was the only one in the bar until she came in. She had been out bar hopping and hadn't found anything to her liking so she decided to swing by the pub on the way home. She had not eaten dinner so I suggested that we grab a snack and a drink together.
We sat side by side at a bar table facing the bar. The bartender Dan, an addicted gambler, 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 her nylon covered thighs. She was wearing pantyhose under her red mini dress but no panties. She always wore panty hose as opposed to regular nylons. I slid my hand between her 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 pub. When we got out to the parking lot I asked her if she wanted to sit in my car as I felt she was ready to fuck.
I drove to a remote spot in the parking lot and we got in the back seat of my two-door sports car. 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 car 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. She had her legs spread wide as I fingered her pussy and pushed her cunt juice into her ass. She stroked my cock with her hand as I prepared her for another ass fuck.
I never knew anyone like who could get so wet during foreplay. My hand was sopping wet and within minutes I had her anus coated with her own pussy juice. She reminded me again had she preferred anal sex to any other. I positioned her 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.
She reminded me as she always did, "Not too deep at first and then deeper."
I eased my cock into her ass as she maneuvered her body to accommodate the anal penetration. She 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. She 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. She had her fingers buried in her twat and she brought herself off as I plowed her ass. When my hips stopped moving she milked my cock with her sphincter 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. She 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.
She 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. She 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 ass. After she left the parking lot, I drove home in a very sated state.
It was at least another week before we 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. That night I wanted to play with her tits so I unzipped the back of her dress and unhooked her bra.
As I fucked her ass the top of her dress was down to her waist and her tits hung down beneath the loosened bra. I leaned over her and grasped her breast with both hands as I drilled her bottom. She was frigging her pussy and within minutes we were both cumming. Once again, I shot a massive load in her ass and she milked my cock dry. As before I handed her napkins to clean up and we redressed before she headed for her own car.
The final time it was another evening at the pub and we were anxious to get at each other. We got in the back seat again and I pulled off her hose. She said she wanted to try to spoon in the car so we stretched out on the back seat the best we could. I unzipped her dress and unhooked her bra as I had the last time. I scooped her female juice from her pussy and used it to lubricate her anus. In all the times, we had anal sex we had only used her juices as natural lube. She 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," she again 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 her 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. She was going wild and she was creaming all over my fingers as I plowed her ass. My cock was throbbing in her ass 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. She instinctively clenched and unclenched my cock with her sphincter. She milked every drop of cum from my cock.
I stayed hard that night and I kept right on fucking her ass. I knew it would be a while before I came again. body. I pummeled her ass as I sought out my second orgasm of the night. Her 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 her anus. We were both breathing hard from the exhilarating anal sex. I finally retrieved the paper napkins and handed them to her. We both moved gingerly and redressed ourselves.
That was our last sex in the car and we only got together one more time. I had taken a job with another company and left town. During the time I had seen Charlotte we had anal sex ten times but the three times in the car were by far the most exciting.
MAUREEN
It was 1978 the third year in my new job when I met Maureen. She was a very different looking young woman as she was as tall as me at 6'1" but she was slender and fit. Her breasts were very small, just little mounds on her chest. There wasn't much curve to her body but she had one thing most tall girls don't have and that was a great ass. It was perfectly shaped, round and protruding. She would not normally be the type of woman I would try to bed but that ass had my attention.
I had been sleeping with a number of women since moving to the town in 1976. I only had two anal encounters but they were both rewarding. I bagged a co-worker Beth twice in the ass after taking good care of her needs. The other was a one night stand with a nurse that I met in a bar late one night. The other women I had slept with were all decent lovers and one of them we stayed together for nearly a year.
It was after a going away party that Maureen or Mo, as she preferred to be called, and I hooked up. She had worn tight slacks that day and I could not take my eyes off of her ass all night. I struck up a conversation with her and she was receptive to my advances. Just before we planned to leave the bar together, she stopped in the ladies' room. A colleague of mine came up to me and whispered that Mo had a reputation of giving great head. I didn't know about getting a blow job but I was definitely interested in the ass.
When she returned from the bathroom, I invited her to my place but she had a different suggestion. She was driving her roommate's van that night and she asked me to sit in it with her. She drove to a remote end of the parking lot with no cars around and then we got in back. She wasted no time in getting to her knees in front of me to free my cock. With her deft experienced hands, she had my pants unzipped, unfastened and pushed down to my knees along with my underwear. My cock was already hard with she took it in my mouth.
Her reputation was well earned as she was an excellent cock sucker. All the while she remained clothed as she sucked my cock, occasionally testing her gag line as she tried several times to deep throat me. I reached over her and fondled her ass through the tight slacks and she got the hint that I wanted to fuck her. She pulled off my cock and she shed her slacks and panties. I followed suit and took off my pants and underwear. We were both naked from the waist down.
From there we stretched out on our side in a 69 position. She obviously wanted to suck my cock and I wasn't going to deny her that. I buried my face in her pussy and she loved it. As we ate each other, I fondled her lovely ass. I tickled her tailbone which sent shivers through her body. I toyed with her nether hole and tested the tightness of the taut rubbery ring. Wetting a finger in her pussy, I began moving her juices to her anus.
I managed to get my middle finger all the way in to her snug hole and she didn't protest. Suddenly she exploded and drench my face with her love juices. I held tightly to her curvy firm buttocks as she bucked and groaned as she climaxed. Her body began to recover and I rolled her to her back. Moving between her legs, I slipped my cock in her pussy and fucked her through another orgasm. She begged me to let her rest but I was far from done with her.
Mo agreeably moved into the doggy position and accepted my cock back in her pussy. As I fucked her slowly I played with her anus. I easily inserted one finger in her ass and then with my other hand I diddled her clit as I fucked her from behind. Getting my fingers wet in her pussy, I was able to add a second finger into her bottom. It was snug bit she did not protest. Satisfied that she was wet and loose enough, I slipped my cock out of her pussy and quickly pushed it in her ass. She reacted to my cock in her ass and her body tensed up.
I pushed more of my cock into her ass. I added more saliva and pussy juice as I fucked her and shoved more into her ass. Another push and my entire cock went all the way in her ass. Her anus 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.
I was incredibly turned on and I could feel my own orgasm approaching. I knew it would be a big one since I was so excited to be fucking her beautiful ass. It 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 bottom. 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 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. Mo flopped face down on the floor of the van and I knelt there watching my seed ooze out of her shapely ass.
I knew then that she had been butt fucked before me since my cock went in fairly easy with the right amount of natural lube and she did not complain of any pain. I stroked my cock back to hardness as I stared at her magnificent ass. I snuggled up to her and slipped my cock back into her ass. I knelt closer to her and placed my cock at the entrance and pushed ever so slightly. I watched as her little rosebud opened up to accept my rod and the cock head cleared her sphincter.
She had her head down on the van floor turned to one side. I slowly fucked her ass and I knew that I would be in her for a longer time before I came the second time. I loved watching my cock slide in and out of her beautiful shapely ass. It seemed like an hour before I came again. 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. Mo 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 second load.
The two of us collapsed on the van floor with me on top of her and my cock still buried in her ass. I could feel her 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. I rolled to my back and let out a loud sigh. She remained on her belly for several minutes before she spoke.
"There is a towel in the sport bag on the back seat, get it for me."
I retrieved the towel as she asked and I watched as she wiped my seed from her bottom. She looked at me as I put my pants and underwear back on.
"Please don't tell anyone that you fucked me in the ass."
"I won't. I never talk about my affairs."
"I guessed that but I wanted to be sure."
We finished dressing and moved back up front. She drove me to my car which at that point was one of a few left in the lot. We said goodnight and I drove home feeling very fortunate to have fucked an absolutely fabulous ass. Mo and I hooked up several times after that but never in a vehicle again. I loved fucking her ass and she was always open to it as long as she got to suck my cock first. In 1979, I took another job and moved to the Chicago area.
BARBARA
By the year 1984 I had worked for this company for five years since moving to Chicago. The company was headquartered in Philadelphia and I worked in the regional office. Once again, I was fortunate with the ladies and hit it off with a number of them. I managed to have anal sex with a couple of them but never in a vehicle. It wasn't until I met Barb in the home office that I had anal car sex again.
She and I had hooked up on my first visit to the home office and then on every visit after that. She was a good lover who gave great head and gushed when I fucked her through multiple orgasms. Best of all was that she also liked anal sex but was very selective about with who she did it. We had dinner one night together and when I drove her home she had me parked away from her condo. She told me her husband was home but she still wanted to have sex before she left me.
We started playing with each other and she had my cock out of my pants in no time. I managed to open her blouse and unhook her bra so I could fondle her small tits while she sucked me. My pants and boxers were all the way down to my ankles and I reached under her skirt and rubbed her pussy. She was getting hotter and hotter. We had never had sex in the car before but I knew she was up for it that night.
"All this playing with your cock has got me hot again. I need to sit on your dick," she whispered.
I sat back on the car seat as she removed her panties, straddled my body and lowered herself onto my cock. She held my shaft and aimed it at her vagina. My hard cock slid easily into her womb and she emitted a small gasp as it filled her hole. Barb rocked back and forth on top of me as I held on to her curvy ass. I stroked her beautiful ass cheeks and molded her firm buttocks in my hands as she picked up the pace fucking herself with my dick. She started moaning as she fucked faster and faster. I leaned in and sucked on her tits and nipples as she rode my cock.
"Sweet Jesus, I love being this full of cock. Fuck me nice and slow."
I let my fingers dip down to her pussy and scooped up some of her juice. Then I teased her nether hole with a pussy moistened fingertip. She never objected to my playing with her ass and anus so I pushed my finger in a little deeper. She was going wild riding my cock and I felt my own release building in my balls. I sensed her pending orgasm and then she buried her face in my shoulder to stifle her screams just as my ejaculation flooded her womb. She stopped moving as jet after jet shot into her from my pulsating cock.
"I am going to explode. Oh, oh hold me, please hold me tight."
She collapsed on top of me her body quivering from the intensity of her orgasm. Her face in my shoulder as she screamed in passion. I could feel her juices coating my cock as it remained buried in her womb. It took a few minutes for her to regain her composure and she just sat on me and cooed. Eventually she moved off of me and sat next to me. She had had two mind blowing orgasms and she was sexually satisfied. However, I was not done with her. As always, she had not objected to the ass play so I was determined to try and fuck her fantastic ass.
Barb noticed that I was stroking my semi-hard cock and she smiled at me just before she lowered her mouth to my shaft. Within minutes she had me rock hard proving that she was an accomplished cock sucker. I was anxious to get at her ass all the while wondering if she would let me fuck her in the ass in the car. I moved her to all fours on the car seat so that she was facing the steering wheel. With her ass elevated and she placed her head on the car seat turned to one side. I started playing with her pussy and her curvy ass lubricating her with her own cunt juice. She moaned and cooed as I fingered her pussy and her ass simultaneously. I tried to get her anus wet enough with her juices and my saliva so that I could fuck her ass.
I knelt behind her and tried to insert my cock in her ass but it just wouldn't go. Afraid of hurting her I tried more pussy juice and saliva for lubrication but to no avail. There are times when my cock feels bigger and thicker and this was one of those times. I was fingering her ass when she spoke.
"Wait let me get some cream."
She reached down and got some lotion from her purse and then she handed it to me. I realized then that she was going to let me fuck her in the ass in the car. I put an ample of amount of lotion in her coating the tiny puckered opening of her anus and lubricating the rim. I added my saliva to my lotion covered cock making it super slick and nestled my dick against the entrance momentarily before easing it inside her ass. I could feel my cock struggle to stretch the resistant muscles. My dick head burrowed in and her rigid passageway soon yielded to the determined action of my cock. Barb moaned as my pecker filled her hole.
"Go slowly at first, no one has been there since your last visit."
I fucked her with long and deliberate strokes until my cock was sliding easily in and out of her ass. I caressed her shapely buttocks as I watched my dick move in and out of her rectum worming around inside of her curvy ass. I caressed her tiny firm tits and tweaked her eraser hard nipples as I leaned over her body and whispered in her ear, "Barbara, I love fucking you in your hot ass."
My hands freely roamed over her body and I pulled her by her hips drawing her backwards impaling her on my bloated cock. I reached for her pussy to finger fuck her and diddle her clit but I found her hand already buried in her womb. She was frigging herself frantically working herself toward an orgasm. Suddenly I felt my cock swell up inside her ass and I started pumping faster. Within minutes I knew that she felt the warm fluid being squirted inside her rectum and she immediately started to cum herself. Her cunt walls convulsed around her own hand fucking as her ass squeezed every drop from my spurting cock. I grunted as my whole body became stiff and I slammed my cock harder into her. She writhed around and her body arched off the car seat as a climax of massive proportion tore through her loins.
My cock slipped from her ass with an audible pop and I moved back against the car door. I caressed her shapely ass and she rotated it in circles displaying her delight. Barb then said that she really needed to get going and I checked the time. We had been fucking in her car for over two hours and it was almost midnight. We both got redressed and then we kissed good night. I drove to her condo and waited until she was safely inside before I drove away and headed back to the hotel.
That was the only time that we ever had anal sex in the car and it was fabulous. We got together every time I came to Philadelphia and we always had anal sex at least once on each visit but never in the car again. I often wondered how many people had sex in a rental car. I was sure that not many had anal sex but it was an interesting thought.
CATHLEEN
I changed jobs again in 1985 but remained in the Chicago area. I had accepted an executive position with a company and I had inherited the administrative assistant from the previous executive. Cathleen was an interesting person and to look at her not one you would expect that I would have an affair with. However, after one year we were insatiable together, not because of her looks but because she was the best lover I ever had.
She did it all. She gave great head, was a good fuck and she loved anal sex with me. At 5'5' she was a fit woman with small tits but a curvy body. She wasn't very pretty but not sore to the eye either. Her hair was strawberry blonde with a course texture. Her legs were solid and toned from all her hours of aerobics. Then there was her ass and what an ass it was. It was a work of art and perfectly shaped.
Once our affair started we had sex whenever and wherever we wanted. In my condo, at the office, in my car, at a romantic interlude. There wasn't a work day that went by that my cock wasn't in her mouth or pussy or ass. Some days it was all three. She was married, so weekends did not work and that was just as well as I could use the rest. Cathleen liked the spoon position and that was usually reserved for sex in the car. She liked having my cock in her ass while I fingered her pussy and played with her tits. I never forgot the first time we had anal sex in my car.
One night after aerobic class, we went to our favorite spot for a couple of drinks. After a few drinks we adjourned to my car so that she could suck me off. As she was blowing me she pushed her spandex down to her knees baring her ass and pussy. I played with her ass and fingered her pussy as she sucked on my cock.
"I wish you could fuck me in the ass tonight."
I asked her if she had any lotion and she dug it out of her purse. I reclined the passenger seat all the way until it was almost flat and had her lay on her left side. I prepared her ass with the lotion. I pushed my trousers and shorts down past my knees, lubed up my cock and got behind her on my side. It was tight quarters but I managed to get my cock into her ass and started banging her hard. She pushed back at me as hard as I pounded her. Soon we were both sweating and breathing hard. We made quite a sight if someone should happen to look in the car window but we were past caring about that as we raced toward our mutual orgasms. Eventually the windows fogged up and no one could see inside although they might see the car rocking. As soon as my spunk filled her ass her body went into spasm with her own orgasm soaking my fingers. I lay next to her until we recovered.
"Do you think you can go again?"
"I think so, it will take me longer to cum."
"I know. I want you in my ass all night. Let's get in the back seat."
With the car windows fogged, we crawled over the front seats into the back. I couldn't help but run my hands over her lovely ass as she moved in back. I joined her and she went right for my cock taking it in her mouth. Cathleen always kept herself squeaky clean and always douched her ass before anal sex. That's why she wasn't ever concerned about taking my cock from her ass to her mouth. She had her legs spread wide as I fingered her pussy and pushed the lotion into her ass. She sucked my cock and stroked it with her hand as I prepared her for another ass fuck. I positioned her so that she was kneeling down on the back seat and I knelt behind her. I put my cock in her pussy first and played with her ass. I loved her in this position and her ass was just so luscious.
I eased my cock into her asshole as she maneuvered her body to accommodate the anal penetration. She had her head down on the car seat turned to one side and I watched her face break into a smile as my cock made its way into her ass. She reached between my legs and fondled my balls. 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 with a passion. She wanted me in her ass all night and I wanted to stay in it forever.
She had her fingers from one hand buried in her pussy and she continued to squeeze my testicles gently with the other. She had another orgasm and I felt her gripping clenching rectum around my shaft. She could seemingly cum all night and she continued to masturbate as I fucked her ass. Eventually I could not hold out any longer and I drove deep in her as I released my second load in her bottom. I leaned over her kneeling form and when my hips stopped moving she milked my cock with her sphincter. I remained in her allowing my cock to soften but before it slipped out, her hips gyrated as another orgasm overtook her. I tried unsuccessfully to keep my cock in her ass as her hips jerked out of control.
I knelt there looking at her recently violated ass and watched as my semen trickled out of her rectum. She remained still for a few minutes with her ass on display. I got my handkerchief from my pants pocket and handed it to her. She used it to wipe the semen from her anus before she sat down on the car seat.
"Wow!" she sighed.
"Wow, indeed," I countered.
We got dressed and waited until my car windows defogged before she went to her own car. I waited until she was in her car and left the lot before I drove home. I didn't remember ever feeling so sexually sated and drained. It had been an incredible experience to fuck her ass in the car.
I again changed jobs and this time went to New York in 1990. Cathleen was my last anal lover in a vehicle but I would always remember that one night in the car.