Carpool Days

It is hard to say where sexual likes and dislikes start entering a person’s life. When a young man starts noticing the curves and softness of a feminine woman, or when a young woman starts noticing the widening shoulders and developing muscles of a young man. I remember where one of my sexual likes developed though, as plain as if I were in that situation again right now.

Carpool was my family’s responsibility in the mornings and in the afternoons; the other family’s mom, Mrs. Marlies, would take us home. This family was wealthy though. I never knew if they were mafia or not, but they had more money than they knew what to do with. She would drive new Jaguars, Mercedes, and BMWs to pick us up at school. I am not talking the wannabe levels of those cars; I mean the big, expensive models. I have always been a big fan of expensive cars, but those days spoiled me forever. Plus, this woman would always wear some of the classiest and sexiest clothes I have ever seen. Even her jeans fit her like they were custom made. Fine wools, silks, and lace would drape her well-toned body and the smell of expensive leather and perfume would fill those fine automobiles each day on the ride home.

I always was relegated to the back seat on the ride home by her spoiled kids who wanted to sit up front and play with all of the fancy buttons, but to be honest, after one day I suddenly was awakened out of my teenage induced daze sitting in the seat behind the right passenger, I never argued over seats again. It was a warm fall day that particular awakening came upon me. I was late coming out of school, so I was the last to get in, and guess what seat I was given? The only reason I did not get stuck in the middle of the back was because they did not want to have to get out of the car when they dropped me off. At the time, the family was using a BMW for carpool duties. That particular car had a folding armrest in the center that, when down, allowed a clear view of the driver from my seat. I realized this when I looked up, as we were pulling out of the school driveway, to see Mrs. Marlies in one of the sexiest outfits I have ever seen on a woman. I was beginning to recognize a sexy woman when I saw one.

She had on a sheer white button down blouse, a short black skirt, and black mules. Best of all from this angle I had, I could tell the way her seatbelt came across her chest, she was not wearing a bra, the skirt was riding very high apparently from her struggling with her kids before I joined this merry carpool, and to my shock, this woman had on a thin, gold ankle bracelet on her right ankle, which drew my attention south to that slender ankle and perfect toes. The gold was such a stark contrast against this lady’s summer tanned skin; I could not take my eyes off of it for a second. I tried to break my stare because Mrs. Marlies could see right in my eyes in the rearview mirror, and this infatuation with this woman’s sexy body was making me uneasy. Then it happened. As she turned onto the main road, she must have knocked one of her expensive buttons on that shirt undone or off with her arm. The thin, expensive material automatically fell away from her body towards the door, and Mrs. Marlies apparently did not feel any contrasting air temps because of the heat of the late afternoon, she did not notice. The way she had her left arm extended straight out to meet the steering wheel though, left her unbound tit wide open to my lust filled eyes. I actually could make out the silhouette and dark brown nipple of her breast as the sun shone through the car.

I did not even realize it because I was so taken by this gorgeous view, but my young body was defying me as it had been for the last couple of years with a huge hard on that was brought on with no warning and was poking my pants out like I had put up a telephone pole in my briefs. A teen boy’s cock is not like a man’s. There is no talking it down once it gets started by changing the thoughts in your head, plus it is super sensitive where even the slightest bump makes it grow even harder hoping for a chance to come out. The rough road we were on and the stiff suspension in that BMW were jarring my cock in my pants, and it was making her tit bounce so beautifully for my eyes-only. Her nipples were erect and almost piercing that flimsy blouse. I felt a bead of sweat develop on my brow now and my eyes were starting to blur. Before I knew it, she had me home. My glorious view was over.

I was really not smooth trying to get out of that backseat and hide my raging hard-on with my book bag to get around the car and turn towards my front door. I had to look like an idiot. Thank god they left so I could let my guard down a bit to get in the house. Needless to say, when I got to my room, I locked my door and stripped off my pants to jack my now hurting cock off to the image of Mrs. Marlies burned into my head. That is the first time I had ever been so thoroughly aroused by a woman, and the sensation I felt was not even close to what little experimenting I had done with girly magazines and girls my age. That was a rough day, but it had me hooked on a dirty little secret I had now about sitting in that back seat.

I cannot begin to describe how that carpool shaped my sexual life. I hated when my athletic seasons would begin and I had to get rides home after practice rather than with Mrs. Marlies. I longed to sit in that backseat and see what classy outfits she had on, what type of sexy shoes she was wearing, what type of ankle bracelet, what color her finely manicured hands and feet may be painted. I cannot begin to describe how many times I had to crawl out of whatever expensive car she was driving at the time and run to my room to relieve my pain and pleasure.

Eventually, their family started taking me with them on weekends to their various homes in the mountains, at the beach, or at the lake. That was hard on me as well because now I was around Mrs. Marlies in bathing suits, casual clothes, and in those sexy classy clothes all weekend long. Plus, her whole family, including her husband was around, so an unintended hard-on may give my secret admiration of this sexy woman away. Now though, I could not only see her legs and feet and side, but I was seeing her firm ass and toned stomach, her tits bouncing around for me like melons. I would just stay in a daze all weekend. This went on for several years. There were certain times as I began to get older that I swore Mrs. Marlies could tell what I was doing. When I would excuse myself to go to the bathroom or my guest room to relieve the pressure, sometimes she would come knock on the door and ask me if I was ok. At that early age, a man does not really even think that a woman may be approaching him, and my God, why would a sexy, mature woman like this take notice of a young man? It never even crossed my mind. I just had this fantasy world in my head that was slowly shaping my tastes in women, and I did not even realize it at the time or really until I was much older what she may be lacking from life and her husband that would draw her to me.

When I was 18, I was still going off on weekends with them, partly because I thought it was cool to be entertained at those fine homes and ride in those fine cars, but obviously, I also longed to be around and close to Mrs. Marlies so I could continue to fill my memory full of images of her for use later in private.

One weekend in particular changed my life forever. The family had taken me to their farm, which was only about 30 minutes outside town, for the weekend. They had horses and ATVs and it was a cool place to go. Plus I got to watch Mrs. Marlies riding those horses too, while her ass and tits bounced. By this time, I was a bit more sophisticated in my knowledge about sex. I had still yet to have a lot of actual intercourse, but I had seen some porn and messed around with some girls to the point of experimenting with oral sex and some penetration. I could now picture Mrs. Marlies actually fucking me in different positions in my head, rather than just remembering how she looked in clothes that day. My fantasies were becoming more vivid, and I had gained some control over my cock where I did not always have to run to hide my bulge or go relieve my pressure. Now I could stay and get a full on image of her glorious female figure and even managed to steal some brushes against her and cheap feels of her legs and body as we rough housed playing sports and things during the weekends. On Sunday, we would usually leave after lunch to come home. That particular weekend was odd though because it was Labor Day weekend, so there was an extra day to deal with, and their family was going to take off from the farm down to the beach house and get everything ready for hurricane season and winter. I could not go with them on that Monday because I always had a hunting outing with my father on that holiday.

Mrs. Marlies offered to take me home early on Sunday morning so that they could get on the road. It had been a great weekend full of activities and fun. Plus, I had gotten to see Mrs. Marlies in everything from a sexy pair of silky pants to tight blue jeans and leather chaps that weekend. I had enough images of her bouncing on those horses to last me for a month. None of the other family members wanted to ride with us into town because they were busy cleaning up and getting ready for the short trip down to the beach. So she took me alone. Much to my dismay that meant I had to sit up front and could not steal glances as easily without being caught.

Of course, she came out to drive the car in leather mules, a sheer, draping skirt that wrapped around her thin waist, and a button down shirt that barely hid her tits and nipples from clear view. Plus she had her hair up in a way that kept it out of her face, but made it dangle loose off her hear. I am not sure I have ever seen her looking any sexier than that moment. The early morning sun made her skin look even darker and it shined through the flimsy skirt to reveal light between her thighs, even though the top was too well wrapped to show what kind of underwear she had on, but there once again was no bra, just like that very first day she came to my attention. I tried to wipe my mind clean as she got in the car and began talking wildly about what a nice time I had had, how much fun this was, and how sorry I was to not be able to go with them to help them take care of things at the beach house. It was nervous, idle chitchat, and it was quite obvious.

This woman was of German origin, and she loved for people to make eye contact with her. So she constantly would scare the hell out of me by looking away from the road to look me in the face, much like she would look me in the eyes through her rearview mirror on carpool days. Actually, I quickly realized that by maintaining eye contact with her, when she looked away I could steal glances fairly easily of this sexy creature who I had completely alone. I say that with a smile on my face, because then and particularly now, what type of move could a 18-year-old boy make on a woman as sexy as this one in her late 30s or early 40s? I was barely even learning to use my southern charm at that time to flirt with women. As feminine and sexually appealing as this woman was, no flirting or idle chitchat was going to budge her to my advantage. I was just smirking to myself as I was slowly but surely looking her up and down as she kept her big Benz in the road, taking in every detail of her body flexing as she spoke and drove; her legs exposed from the dress opening down the slit on top of her tanned thighs, her natural tits pushing almost through the sheer material, and her feet working the pedals of the car with the gusto of a professional race car driver. I have to say, the fear of her seeing me with a hard-on kept me subsided for a while, but eventually my body betrayed me again and I felt a hard-on coming on strong. I was becoming a man now too, so these hard-ons were not nearly as easy to conceal from view. This was a big problem for me. I adjusted in my seat to give more play in the crotch of my pants.

It did not go away either, I was only barely able to hide it from view. Then I about died because as we were going down the road, she asked if I minded if she stopped by her city home for something she needed. Of course, I said no, hoping that during the time she was gone, I could have time to recover. I did not even think about it, but as she pulled into her driveway and opened the garage, she asked me if I could help her grab something that was rather heavy. My first thought was to claim I could not due to an injury because there was no way I could stand at this point, much less help her move something. I could not say no when I made eye contact with her though, and I agreed, trying not to show her how reluctant I was. As she pulled into the garage and parked, I tried to be cool by letting her get out first, and then I stood up and used the car door to hide my manhood at full salute. I pretended to stand back to allow her to enter her security system code to disarm her alarm. She turned to enter, I quickly moved to the doorway, and allowed her time to lead me up the stairs to the main level of the house. The bad news to my situation was, as I let her go in front, the only thing I could see was her draping skirt highlighting every curve of her firm ass which now was only inches from my face. I tried to look down and away, but then I caught a glimpse of her sexy calves and feet pushing her lean body up the stairs. My cock just stayed hard and I was beginning to feel precum forming in my pants.

She led me back into the main den, where she had a medium sized trunk that had swimming clothes and kids toys in them. She explained briefly that those items were being taken to the beach house for storage. I just was concerned about my bulge and got down on my knees behind the trunk to pull some of the loose items inside and close it up. Then she grabbed one side and I grabbed the other and lifted it so it concealed my problem from her view. Now I was staring at her well-toned arms holding the slight weight of the trunk and her tits grouped in between them, with her hard nipples pointed right at me. We slowly maneuvered through the big house and back down the steps to the garage. She asked me to sit the trunk down while she opened her car, and I squatted down with it to try and hide myself. We got it in the car, but just as she let her handle go, a tiny nail grabbed her skirt and tore the thin material right down the front. We both heard it, and I was afraid for a second, as absurd as it sounds, that my cock had busted through my pants from the pressure and pain I was feeling, but it quickly became apparent that it was her skirt because it fell to her ankles exposing her gorgeous lower body and sexy ass with a skin colored thong dividing those sexy cheeks of hers. Usually, I would have been embarrassed, but this was my first ever chance to catch a glimpse of her this naked, and I was just staring without regard. She scrambled to pull her torn skirt, around her, and quickly stole a look at me that was one of shock and strangely sexual at the same time. Then I realized I had turned and my hard on was only inches from her face as she was bending over to hide her exposure. The one thing I feared this whole time, now did not bother me. I stood there too taken by this woman’s beauty and sexuality to be concerned with my own situation.

My manners came through though, and I quickly said something to comfort her and offer her assistance. There was no blanket or any large item to cover her around. So I quickly helped pick up the other half of her skirt and handed it to her to cover her slightly covered pussy lips. I held her arm as I moved her to the door and into the house, and without even thinking, I assisted her in front of me on the steps to get her into the main area of the house. All I had a view of now was her bare ass bouncing in front of me, in vain of her trying to hide it. I was about to pass out now. It seemed like all of the blood was in my cock and out of my head. We soon reached the top of the stairs and I felt dizzy. She asked me to stay in the kitchen while she went and changed. I gladly obliged because I could not take anymore of this. My mind was blurry and my cock was now really beginning to hurt from the pressure. I moved to the glass windows on the back of the house. Staring out over the pool and Jacuzzi and the big back yard they had. Then something caught my eye on the right. This house was three stories and it wrapped around on the right like a half horseshoe. The master bedroom was all the way out on the tip of that wing, and she was now in there with her blinds open.

She had dropped her cover and all she had on now was her thong. Her shirt and torn skirt were in her hands. For the first time, I saw this woman as close to completely nude as any time before. Her breasts were exposed, her ass was swaying around proudly, and her whole body was a gorgeous brown color. I could not see her bottom legs because of the wall, but it put me over the edge. Without even thinking I pulled out my swollen cock and stared at that beautiful creature while I stroked it just as I had so many hundreds of times before, except this time, instead of an image in my mind, I am seeing her nude for real and I was out in the open. I had the advantage too, because the sun was facing me. She could not see me for the glare, and I could make out every detail of her with the sun behind. Soon, I felt it building. I had no regard for what I was doing. I just let it fly. It went everywhere after so much teasing and holding back. It hit the glass door, the floor, and was running down my hand, shaft and balls. Somehow during that explosion, I had lost track of her, only to my utter shock to hear her voice while I still had my cock in my hands dripping with cum.

“You must have enjoyed that show huh?” her voice was deeper than normal and it jolted me from a state of pure pleasure to a state of utter fear.

I turned around, unable to speak a word; my cock still in my hands, only to see that she had closed on me now. I was mortified and scared to death. She was dressed in a one-piece sundress. I did not even notice her clothes except for the fact that they were brightly colored and contrasted with her dark skin. I turned my eyes down to the floor to avoid eye contact like a whipped puppy. Then I saw her sexy shoes come into my sight on the floor. I glanced up just enough to see her examining the mess that I had made all over her kitchen and glass doors. Then she turned and looked at my cock and all of that cum dripping from its tip.

I was too afraid to even move, much less cover myself. I had no idea what was happening. Just then, I saw her move her hand towards me and felt her soft finger drag up my cockhead until it was covered with fresh cum. The feeling of that sent shivers down my spine, but did nothing to shake loose my utter fear. Then I felt her other hand land on my chin and pull my face up until we were making eye contact. She grabbed my chin and prevented me from moving. Then gazing into those gorgeous, gray blue eyes, she moved her finger, soaked in cum, up and slowly slid it in her mouth. She pushed that well manicured finger in and out of those sexy lips cleaning off every last drop of my cum like she had been starving for weeks.

I had no idea what to do next. She let out a moaning sound as she backed her finger out, holding my chin in place. I think we were both realizing that this had gone way too far. But neither of us seemed to care; me because I was frozen with fear that the woman I had secretly worshipped had now just caught me more red handed than possible, and I think she was concerned because she was looking into my young eyes, now filled with fear, but she was rolling my cum around in her mouth like a fine wine. A small drop was on the edge of her lip, and she slid her tongue out to grab that too. Neither of us said a word. She closed on me and my cock buried into her belly pushing her back just a bit. She looked down and released my chin so that her hand could pry my fingers off of my still hard cock. She grabbed my wrist and pulled my hand up to her mouth. My eyes followed her every move like I was hypnotized by her fingers, where she slowly started sucking the cum off the back of my hand and moving each finger in and out cleaning them off.