High school had been an uneventful time for me. For the first three years just a little of the usual teenage drama but fairly normal in most respects. I was a jock and hung out with the guys on the baseball team most weekends with the occasional date to a school event but I never had a serious girlfriend. Being tall, skinny, and very shy was not the babe magnet physique or personality that girls went for. I did manage to become friends with a few girls and we talked a lot. They mostly saw me as a peer and friend but not so much as a boyfriend. On the other hand, some of my teammates were quite prolific at home runs with the girls so I got to hear about their conquest in the locker room most Mondays after weekend sex adventures. Between having friends of the female persuasion who liked to talk about their boyfriends and the locker room banter, I learned a lot about relationships both physical and emotional.
At the end of junior year, the coach called me into his office to talk over my future in the game. He told me several college scouts had asked for info and film on me. Some small local schools but I was still floored that anyone would even notice me. The consensus of the college coaches he spoke with was that I had talent but needed to put on some muscle mass to add a little more power to my game. My coach offered to set me up with a weight trainer that could teach me some workouts specifically tailored to my needs. I excitedly agreed and set my mind to the task of muscle building all summer. With the trainers' help, I developed a two a day work out and a diet supplement program based on high protein and carbs. Getting a scholarship to play baseball was a real goal for a lanky seventeen-year-old. I did not need the scholarship to go to school because I came from an upper-middle-class home. My parents owned their own business and were highly successful. I just wanted to see if I could get a free ride to college and continue to play the game I loved at the next level.
I turned eighteen at the beginning of senior year and had put on thirty pounds of muscle and felt like a million bucks. Now being six three and weighing two hundred and ten pounds changed a lot of things but the biggest change was the way girls looked at me and openly flirted with me. It was as if they were seeing me for the first time and they liked what they saw. I loved all the new attention but was too focused on getting a scholarship to really develop any relationships. I continued to work out twice a day and this brought me to school early each morning during the week to lift and then shower before class. Some of the other jocks at school followed the same routine at least three times a week. One morning a couple of my teammates made comments about the size of my cock while we were in the shower. Nothing gay but just the usual ball-busting talk.
"Dude, we need to start calling you tripoded. You could kill someone with that thing."
"How do you get that in a cup? It must be painful."
I never gave the size of my cock much thought and only had porn to make comparisons to an erect penis. I was the same size as some of the porn stars when erect so I figured that I was a normal size. My friends' comments had me thinking so later at home I took measurements while watching my favorite porn star, Emma Mae, taking it up the ass. Eleven and a half inches from tip to the base above my balls and a girth of seven- and three-quarter inches at its widest point, the base of the head. It was hard to gauge the size of my balls but they felt about the size of golf balls. After blowing a huge load for Emma's sole enjoyment, I did a little research on the internet and sure enough, I was considered quite above average in the meat department. Someday I would have to put it to the test with a girl and see what she thinks. Meanwhile, it was just me, some porn, and my right hand that extracted large amounts of cum on a regular basis. I did entertain myself sometimes by seeing how much and how far I could shoot a load. My personal record was five feet and a quarter cup of cum. Teenage boys are easily amused and horny all the time, what can I say.
Baseball season had come and gone and I had a great year and a lot of fun. I got an offer from a local college about twenty miles from home. It was not a full ride but it did pay for tuition and I would get to keep playing so this was pretty exciting for me. The college had a very good Engineering program which is what I planned to study. My parents surprised me later that year with some life-changing news. They had sold their business for an astronomical amount of money and were planning to buy a large sailboat. They had always loved to sail and wanted to make it their new lifestyle. This meant I would be spending most of the remainder of my senior year home alone while they took the boat out on short trips making it ready to become a liveaboard. My older sister had graduated the previous year and was a first-year student at a large university three hundred miles away. It dawned on me that having a nice house on the beach with a private pool all to myself would mean a lot of opportunities to party with friends as well as develop some romantic relationships.
Eighteen, horny, and with free time now that baseball was over, I needed to get laid. My prolific porn watching was just making me more in need of the real thing. I started watching more informational and instructive videos instead of the bust-a-nut jerk-off porn. I was trying to learn what to do with a real girl and you know jerkoff porn has little to do with real sex. So, homeschooling in the finer art of fucking and working on my communication skills was giving me confidence and desire. It was time to find a real girlfriend and start dating.
I set my sights on Allison, a senior cheerleader and one of the hottest girls in school. Hey, if you are going to go for it you might as well go big. She was blond about five foot six with a perky, friendly personality, perfectly shaped firm tits and an ass so tight, you could just picture it naked bouncing on your cock. I did just that many times while stroking one out and pumping her full of cum in my fantasies.
Allison spent most of her time with her two best friends, also smoking hot cheerleaders at our school. Kelly, Cat, and Allison had been best friends since first grade and were inseparable except when Allison developed a serious relationship with an upperclassman last year. I learned she had broken up with him a few weeks ago. He went off to school this year and she found out he was screwing around. It is hard to comprehend that level of stupidity but some guys are just true morons.
So, it was Allison and her two BFFs together again. On Fridays before football games, all the cheerleaders would wear their uniforms to school for the pep rallies and when these three would walk down the hall in their short skirts and long legs midsection exposed and tits lifted up and out, everyone noticed. Guys, girls, teachers, the janitor, the six o'clock news crew, everyone! They seemed to not really react to the attention they drew or they knew what they were doing and loved it. The three never acted like hot stuff the way some girls do; they were always friendly and talkative to everyone around them.
Allison was in several of my classes so I planned to sit with her in class as much as possible. After a few days we started talking, she was friendly and even a little flirty. It was hard to concentrate on our conversations while looking at her, she was so attractive I would lose my train of thought but with my recently acquired skills at talking to girls, I managed to keep her engaged. She really seemed to enjoy talking to me so I got up the nerve to ask her out. She accepted and we made plans for Friday night to go to a movie and out to eat afterward.
Now I have to say that Allison was often the recipient of large loads of my cum over the past few months. These were sprayed on her face and tits and deep in her cunt as I visualized her nude form under me while self-satisfying. In other words, she was my go-to jerkoff fantasy. To say that I was excited to be actually going out with her was a mild understatement.
Friday arrived and I polished the meat poll one more time while showering before going to pick her up. I didn't want to deal with a boner all night while we were together so I thought a little pressure release was in order. She was wearing a thong and nothing else. I pulled it across her left ass cheek while I pumped a load into her hot sweet imaginary cunt and all over her imaginary ass that was perfectly tan and firm. As I said, I needed to get laid.
When I picked her up, I got a chance to meet her parents who were very nice. Her mom was a beautiful woman who took great care of herself. Allison came upon her beauty quite honestly as the resemblance was striking. Her dad was very friendly and knew a lot about baseball so we hit it off well. They told us to have fun and be safe and off we went. Allison was wearing a light blue sundress cut low in the front revealing the tops of her full breast. The dress was above mid-thigh so her tone shapely legs were on display as well. She smelled like cinnamon and apples, the combination of all these things made my cock stir and I soon realized it was going to be a struggle to hide it all night. Fortunately for me, a movie was the perfect choice for discretion and camouflage because she was causing all kinds of blood flow to my cock. I suppose this was all self-inflicted because of how I had fantasized so often about her my cock was reacting on instinct like Pavlov's dog.
The movie was good and gave us an opportunity to talk about the details of the plot while we started off to a restaurant. Allison told me she wasn't hungry and wanted to go somewhere to just hang out and talk. I told her that because of my training I had to eat on a schedule or I would start to feel bad. I suggested we go to my house so I could get a protein shake and we could talk there. She was excited by the idea.
I fixed a shake and offered her a beer or wine. She asked if my parents would be OK with an eighteen-year-old drinking in their house. Some parents would not allow that but I told her my folks were sailing for the next two weeks and even if they were home, they would not mind as long as she was not driving.
She accepted a glass of wine and we took it out to the pool where it was cool and the ocean sounds were soothing. I was happy to go outside to a darker atmosphere so it would be easier to hide my ever-present twitching semi-hard cock.
We talked and laughed about school and the weird things high schoolers do at times. She told me all about her plans to go to Florida State in the fall and I told her about my opportunity to continue playing baseball next year. Allison was becoming as pleasant to talk to as she was incredible to look at. My nerves as well as my cock had settled and I was at ease with her. After her second glass of wine, she mentioned the pool looked very inviting.
"You are more than welcome to take a swim. My sister has some swimsuits upstairs that would probably fit you." I said.
Allison smiled and said, "It's pretty dark and private out here, I don't think anyone can see us so let's go skinny dipping."
Before I could respond, she downed her wine, stood up, and pulled her dress over her head. She was facing away from me so her perfect ass came into my view clad in a black thong just like my fantasy earlier in the day. I did not see her tits when the bra come off but when she lowered her panties and bent over to step out of them, I could clearly see her pussy and firm ass. They were more beautiful than any of my fantasies. She ran forward and dove into the pool with a perfect arch. I was stunned, speechless, and hard as a rock. How am I going to get into the water without her noticing? I took off my shirt and shoes turned away from her view and lowed my pants. She started to swim away from me towards the other end of the pool so I quickly took advantage to strip completely and jump in before she turned back in my direction. The cool water helped a little but not much, my cock was at its full eleven plus inches.
