0 comments/ 6687 views/ 8 favorites Planes, Trains and Automobiles Ch. 01: Penny By: walterio AUTHOR'S NOTE: Thinking back I recalled the numerous times that I had sex in a vehicle and I decided to write about those times in my life. My first thoughts were to rank the encounters from the least memorable to the most memorable. However since the best car sex partner ever was also my last, I decided to just go in chronological order. CHAPTER 01 - Penny 1963 CHAPTER 02 - Erica 1963 CHAPTER 03 - June 1967 CHAPTER 04 - Jackie 1969 CHAPTER 05 - Charlotte 1971 CHAPTER 06 - Pam 1975 CHAPTER 07 - Michelle 1978 CHAPTER 08 - Joanie 1981 CHAPTER 09 - Sue 1982 CHAPTER 10 - Cathleen 1986 - 1989 ***** INTRODUCTION I graduated high school in June 1959 and entered the Marine Corps in July 1963. I was a high school athlete and I was 6'1" and a fit 190 pounds when I reported for duty. I am not going to discuss the car sex as an 18 year old in high school as most of it was mutual masturbation and oral sex usually in favorite parking spots and drive-in theaters. Also I will leave out the car sex in Italy where I was stationed for two years. Most of that sex was with ladies of the evening and took place in the back seat of someone's car. It was most often oral but at times a woman would ride my cock. My story will begin in the fall of 1963 after my four years in the corps. I was living in New Jersey near a major University and attending classes three nights a week. I was working in New York City and commuting every day to and from work. I didn't have much money to start with so I did not own a car and renting a room was the most economical way to live at the time. The house was just a mile from the campus and on the bus route to the city. It was a good set up for starters. I had friends who would give me rides when I socialized with them and dated a few girls with cars. CHAPTER 01 PENNY - SEPTEMBER 1963 Penny was in my English class and I sensed that she was attracted to me. I was 6'2", 190 pounds with short brown hair, hazel eyes and very fit at the time. When I was discharged from the corps my body was chiseled and I was very proud of my fitness. I continued to take care of my body and stay in shape. I thought that Penny was pretty cute so I befriended her and one evening after class we stopped for coffee. I was surprised with how much she shared with me that night at the diner. Penny was divorced for almost a year with two young children. She had been in an abusive marriage although it didn't start out that way. Penny married at the young age of 21 to a man of 27. Penny learned that she could become pregnant easily and they had two children within the first two years of marriage. Her husband worked in construction and it the early years they had a decent marriage. Then her husband started drinking and carousing in the third year of their marriage. He was out every night and sometimes he didn't come home at all. Penny guessed that he started sleeping around. It was true when her husband didn't come home he was shacked up somewhere and if he did come home he was usually drunk and abusive. He would force Penny to have sex with him even if she did not want to. The sex in their marriage became one way as her husband was only interested in his own satisfaction. He would force Penny to suck his cock until he came in her mouth which she despised. He would fuck her until he came in her pussy not caring whether she orgasmed or not. One night he took her ass and he ignored her screams and pleas as he ravaged her asshole. Penny recalled the immense pain and degradation of that night many times thereafter. Finally enough was enough and Penny went to her parents with her story. Penny's father hired a private detective to watch the husband and in a short time they had evidence of his infidelity. The divorce was filed and settled quickly. Her husband didn't even try for custody of the children and he wasn't interested in visitation rights either. Penny knew that the child support payments would not be sufficient to live on so she took a part time job and then applied to college. She was accepted at college and began night school in the fall of 1963. She was still a very pretty young woman at the age of 26. She had light brown hair, brown eyes, 5' 5" tall, weighed about 110 pounds and she had a cute curvy figure. Penny was not a big woman but she had the bumps in the right spots. Her firm breasts were 32 B with hard nipples. She had a narrow waist, shapely legs and a really cute butt. She was conscious of her bottom as she felt it stuck out more than she would have liked. Too many times there were the so called accidental brushes and bumps into her buttocks. Penny wore fuller skirts most of the time to hide her shapely bottom. I shared my time in the Marines with her and she loved hearing about Italy. She was amazed at the training regimen to be a Recon Marine which followed my tour in Italy. It was Recon that kept me in great shape until I was honorably discharged. Penny and I finished our coffee and she gave me a ride home. We parked in the driveway and it just seemed right to kiss her goodnight. She tentatively returned the kiss and seconds later our lips were locked together. She owned a station wagon with bench seats, common in those days. I pulled her over to me on the passenger side and she settled between my legs. We continued to kiss and before long I was stroking the back of her legs. My hands came up to her bottom and I ran them lightly over her panty covered buttocks. She was moaning softly but clearly struggling with how far to go with me. Finally she sat up and I could she see was shaken. Pulling her dress down she whispered as if someone would hear her. "Walt you are very gentle and I am sure that you would be a good lover. I'm just not ready." "That's okay, I understand." "I would like to see you some more. I hope we can do that." "Sure, I'd like that." "I have to say goodnight now." "Goodnight and thank you for the ride home." I kissed her on the cheek and then got out of her car. I had a throbbing erection that was snagged in my pants and it was almost painful. Penny drove off and I entered the house and went right to my room. I shed my suit and put on workout shorts and a tee shirt. It wasn't too late so I had a scotch rocks before I went to sleep. Sitting up in bed sipping my scotch I thought about Penny and where things might go with her. I was 23 and she was 26 years old but that didn't matter to us. However, she had two kids and I certainly wasn't ready for a relationship that would lead to marriage if that was what she might have in mind. A week later it was coffee after class again and a similar scene in the car. In fact that happened a couple of more times and then one night we cut class and went to the drive-in theater. We cuddled watching the movie as she sat in the middle of the front seat. That evening she was wearing a sweater with a full skirt. I let my hand go up under her sweater and cupped a small but firm breast through her bra. Minutes later I had unhooked her bra and her bare breast was in my hand. She was moaning softly in my mouth as we kissed and I fondled her breast and tweaked the stiff nipple. Penny loved having her breasts fondled and kissed. The car windows steamed up and we were not visible in the car to outsiders, I pushed her sweater and bra up and covered her cute tit with my mouth. She went wild and her head was thrown back moaning softly. I ran one hand under her skirt and pulled the panties to the side. It would have been too much for her to deal with if I took them off. I played with her pussy and stroked her stiff clit. Easing one then two fingers into her, I quickly located her g-spot and she began to hump my hand. Between me rubbing the g-spot and her clit simultaneously she went wild and had a massive orgasm. She covered her mouth with the crook of her arm as she cried out in ecstasy. Her body thrashed about and then shivered as she exploded and slowly recovered from the intensity of her climax. She was breathing hard and deep when I freed my cock and balls through the fly in my pants. My 7+" pecker was throbbing for attention. I tried to lift her onto my cock but she wasn't ready for that. She stroked my cock with her tiny hand and lowered her mouth to it taking in just the thick soft mushroom head. She didn't want me to cum in her mouth and I promised her that I wouldn't. She continued to stroke me and suck the head of my cock until I told her that I was close. She stared at my cock waiting for it to erupt as she jerked me off. "Penny, I'm going to shoot any second now." She kept stroking me and I was sure she could feel the surge through my shaft. The first shot nearly hit the roof of the car. She gasped and let go of my spurting cock so I had to grab it and stroke it. She just looked on in amazement as I fired about five forceful streams onto the passenger side dashboard. I continued stroking my cock and then squeezed the remaining semen from it. Digging my handkerchief out of my pocket I wiped off my dick and then wiped down the dashboard. "My God, I have never seen anyone cum like that. I couldn't imagine all that going into my vagina and certainly not my mouth." "Yeah, I haven't cum in in a week and I was ready." "I'll say." Penny started the car and turned the defrosters on full. I put my cock and balls back in my pants and fastened her bra for her. We straightened out our clothes and waited until the windows cleared up. I placed the speaker back on the stand and we drove out of the theater. We didn't speak of the sex as she drove me home but when we got there she thanked me for a nice evening. We kissed goodnight and made plans to get together that coming Friday for dinner. It would be the first non-school night that we would go out. I sensed that she was ready to make love and I looked forward to it. I had classes on Wednesday and Thursday nights and I was swamped with homework. It was a good thing that I was going out with Penny on Friday because I needed Saturday and Sunday to get the school work done. It was a little disappointing because this girl Erica wanted to do something on the weekend. I was whipped on Friday evening after the commute home and under different circumstances I would have cancelled plans with Penny. It would have been upsetting for her after getting a sitter for her kids and besides I was hoping to get laid that night. We had a nice dinner at a fine restaurant and as much as it cost me I was determined to have sex later. We drove back to the house but I could not convince her to come inside. Instead we sat in the car in the driveway kissing and petting. It wasn't long before the windows were steamed up and I had her bra unhooked and this time she let me take off her panties. I laid her out on the front seat and moved my face toward her pubes. She was trembling as I kissed the smooth skin of her inner thighs working my way to her pussy. Once I licked her vulva she nearly flipped out. I gently kissed her and made love to her orally. She held my head tight to her quim as she relished every second that my mouth was glued to her pussy. I nibbled the hard clit and she screamed aloud with pleasure. With one hand I unzipped my fly, unbuckled my belt and unfastened my pants. Kneeling up I pushed my pants and underwear down to my knees. My cock was so hard and so ready I just had to have her. Gently prying her legs apart and moved between them and eased my cock into her moist pussy. It took her breath away when my thick shaft filled her womb. "Don't cum in me. I'm not safe and I'm not on birth control." I didn't have any condoms on me and I wasn't about to go in the house to get one. The last thing I wanted was to risk getting her pregnant. I fucked her slowly enjoying her body and trying to hold off on cumming. She was going bonkers and I suspected it had been quite some time since she had a cock in her. She wrapped her legs around me and held me to her. I could feel my balls tighten and my toes curl in my shoes. I was close and I had to pull out. She tried to keep me in her but I was strong enough to back out and free my cock from her pussy. I lay back down on her using my arms to keep my weight off of her. My cock began spurting between our naked bodies and we both could feel the warm semen coat our bellies. "That's disgusting, why did you cum all over me?" I was shocked by her reaction and statement. "You told me you weren't safe, what did you expect me to do?" "You should have got off me and jerked off." I knew at that moment that she and I were through with each other. I sat up took out my handkerchief and wiped my seed off her belly. I got redressed the best I could and sat up. "Get out, I need to go home and bathe." I got out of the car without saying another word. She drove off in a hurry and I went in the house. It was disappointing because up to that time we got along good and had some decent sex. I surmised that penny was a head case and would be a liability going forward. Once inside I changed clothes and poured a stiff scotch. I was watching TV and nursing the scotch when the phone rang. My landlady was not home so I answered the phone and it was Erica. She asked if I wanted to go bowling Saturday night with her and some friends. I accepted as I could spend the day studying and enjoy a night out. It would be a pleasant break after the ordeal with Penny. I continued to see Penny at class the rest of the semester and I was polite toward her but we never did go out again which was fine with me. NEXT CHAPTER The next chapter will be about a German girl named Erica who I met at a singles group. She had one fantastic body and we had great sex together both in bed and in the car.