I enjoy reading stories about peoples first sexual experiences. Here's mine. I went from being totally unexperienced with either male or females to what I refer to as a triple header in one day.
It was many years ago in the late sixties when I was a junior in high school. I lived at home with my parents in a house that shared a driveway with our next door neighbor. They had two kids, Ralph, who was about a year older than me but still in the same grade, and Laura who was a couple of years older than Ralph. Ralph and I were in the same Math class and Laura had graduated a couple of years ealier.
My bedroom was on the second floor and faced the driveway. Both Ralph's and Laura's room also faced the driveway, as did a bathroom between them, but they were all on the first floor. All three of their rooms had venetian blinds which, if left in the right position, would give me a clear view into the rooms. Since this position also completely blocked out any view from the driveway, this is the position they were usually left in.
It didn't take me long after moving in to discover these views and I would keep a pair of binoculars on my desk just for this purpose. I told my parents they were for bird watching as I also had a very good view over their house into a near-by park. Many times at night I would lie in bed waiting until a light came on in one of their rooms. Then out came the binoculars. Laura was well built but never seemed to have many male friends. Several times I would see her with other girls in various stages of undress. Unfortunately the lights usually went off before the underwear came off, but she did have a dark red bra and panty set, with matching stockings and garter belt that always turned me on (and fortunately she wore it a lot). No matter what she wore I would usually end up with a big hardon that needed manual relief. That was, up till that time, my only sexual experience of any kind.
Ralph on the otherhand liked to leave the lights on and walk around in his underwear. In those days you could get any color you wanted as long as they were white. He almost always wore jockey shorts which showed a nice bulge. Occasionally he would wear a jock strap and sometimes just a towel which would occassionally open to reveal his cock. Whenever this happened again I would get a hardon and have to jerk off. He had a nice cock which I guessed to be about 6". Other than the ones I saw in the showers in the locker room it was the only one I had seen close-up (at least using the binoculars).
In their bathroom the toilet was under the window. If the blind were open, or if the slats were angled that certain way, I could see anyone using the toilet. With Laura since she always sat to do anything, I could only see her back. Occasionally I could get a brief view of her pussy and tits when she was naked and stood in front of the toilet before turning round to sit down. With Ralph I got to get a good view of his dick whenever he took a piss, I also got to watch him jerk off a few times. Their parents must have had their own bathroom because very I never saw either of them in this bathroom.
One night Ralph and I were in my room studying for a math exam when the light bulb burned out putting my room in total darkness. I went downstairs to find a new lightbulb, and when I returned saw Ralph looking out the window. While I was replacing the bulb he commented on what a good view I had of Laura's room. I tried to mumble some half-baked answer when he told me not to turn on the light, but to close the door and come over. When I did we could clearly see Laura with one of her girl friends, both in just their lingerie. Laura's friend left the room at which time we saw the bathroom light go on, and her friend drop her panties and sat to do her business.
I immediately closed the blinds and turned on the light. Ralph then asked me if I had ever watched him in the bathroom. I tried to say no but was turning a bright shade of crimson so Ralph new I was lying. He told me he didn't care, that he liked to jerk off occasionally and kind of had an idea that I watched. I tried to get back to studying but he quickly turned the topic of conversation around to sex. He asked if I had ever played with a girl. I said No. He then asked if I played with myself. I tried to say "no" but he could tell from the fact that I was turning red that I had. He admitted that he often played with himself and then brought out some magazines out of his backpack (or knapsac as we called them then) which showed naked men and women. In those days that's all that was available. I was hoping he wouldn't notice that I was as interested in the pictures of the men as I was of the women or the fact that my dick was getting hard.
He then said he was tired of studying and asked if I wanted to play cards. I agreed hoping it would change the topic from sex and the magazines and we started with a couple of hands of poker. After a few hands he asked if I wanted to make things interesting and play a version of strip poker. After I agreed he told me that in his version the winner would take off a piece of clothing everytime they won (or would have the option of having the loser put a piece back on). Once someone was naked the next time they won the loser would have to jerk him off. I tried not to appear too anxious and agreed to play. As it turns out Ralph was a much better player than me and the first time Ralph won he took off his pants. From that point on I had a hard time looking at my cards and not the growing bulge in his shorts. It wasn't long before Ralph was naked and then of course I lost the next hand. Ralph immediately reached over and grabbed my hand and brought it over to his cock. I rapped my fingers around it and was amazed by the warmth. Even though it was so rock hard is still felt soft as I stroked my hand up and down. I tried not to stare but couldn't take my eyes off his cock as a clear liquid (what I soon learned was pre-cum) came out of the end. Within a few minutes I felt him tense up and his cock throb as several spurts of cum came flyout out just missing my face. We cleaned him up and went back to studying.
These study sessions continued on a regular basis for quite a while. Usually Ralph won but occasional I did and also enjoyed being jerked off. One day were were "studying" over at his house and during one game Ralph asked me how often I watched his sister in her bedroom. I denied it but he said he had seen me with my binoculars. I admitted it and told him about the red underwear that really turned me on. He then asked if I would like to change the stakes to the card game. When I asked about the changes he said just trust him. I agreed. In this game I started winning and was down to just my underpants, he then started a winning streak and went down to his underpants. Then I won again and was nude with a bit of a boner sticking straight up. He won the next hand but instead of taking off his underpants said he wanted me to put something back on. I reached for my underpants to put back on when he said no and left the room. He came back with a small bag and pulled out his sisters red panties and told me to put them on. I tried to refuse but he said he would tell all my friends I like to jerk him off, so I agreed and put the panties on. As soon as I did my cock got even harder. He also won the next several hands and I ended up adding the red bra, with some socks as stuffing, and the garterbelt and panty hose. I tried to object but realized that I was really getting turned on by this and would have done almost anything he suggested.
The next hand he won so I started to reach over to start to jerk him off, but he said no, I had to give him a blow job. Before I could object he stood up, then reached over and grabbed my head and pushed it down to his crotch and started to rub his cock on my lips. I tried to resist but he bent my arm back and as I opened my mouth to scream he shoved his cock in. My initial reaction was to gag but I soon realized that it felt good. Not being experienced at this I took the word literally and clamped down on his cock with my lips and tried to blow out. It sounded like a big fart. After he stopped laughing Ralph informed me that even though it was called a blow job it was really sucking cock. Then I stated to apply suction and as I did he started to move his cock in and out of my mouth. At first I was massaging his cock head with my lips and tongue and loving it. Occasionally I could taste his pre-cum and started to like it.
This continued for several minutes until I could feel his cock start to tickle the back of my throat while I could feel his pubic hair on my lips, nose and chin. I was really starting to enjoy it when we heared his bedroom door open and standing there was his sister Laura and her boyfriend (I later learned his name was Paul). Both Ralph and I were scared shit-less and immediately lost our hardons. Laura's boyfriend just stared at us for a while and then said something like "Look what we have here". He then whispered to Laura, pulled out his own cock which was bigger than Ralph's, and said "If you want to suck cock, how about trying a real one." He then walked over to me and ordered me to open wide. I did and he stuck his cock in. At first I was scared and shaking and didn't know what to do with this limp thing in my mouth. As he forced my head back and forth he started to harden up and I got my first exprience at what I now think is the greatest feeling in the world, feeling a cock getting hard as you work on it with your mouth. It wasn't long before he was hard and I glanced to the side and saw Laura playing with herself. Paul them pulled out of my mouth, turned to Laura, and said "Hey hon, lets show them what a cock is really used for". He then reached into his pocket, pulled out a condom, and proceeded to put in on his stiff cock. Laura pulled off her blouse and shorts, pulled her panties to the side and they started fucking, making both Ralph and myself get real close to watch.
After a few minutes he went stiff and let out several gross noises, then pulled out of her pussy. We could see his dick becoming limp and a large wad of cum in the tip of the condom. While he seemed satisfied from the grin on his face, Laura appeared visually pissed and yelled at Paul saying somethins like, "As usually you cum so damned fast I never get a chance to get off". Paul then turned around and started to finger fuck her pussy in an attempt to get her off. Laura then pushed him away and turned to me saying "No, she looks so sexy in my underwear, let her finish me off. I moved over and was about to stick my finger up her pussy when she grabbed my head and forced it into her crotch, at which time I started licking her pussy until she came.
They then got dressed and as they were about to leave Laura came over to me and whispered "As long as you look like that you can do me anytime".
Neither Ralph nor myself said anything for a while but soon got back to our card games in which I regularly put on lingerie and ended up sucking him off. About a week later as I was passing by Laura's window she asked me to come in, gave me a set of green lingerie to put on and we played with each other for what seemed like hours. As long as I was wearing her underwear I could do anything to her I wanted. That is to start with. As time progressed she seemed to lose interest in my cock and only let me fuck her if I wore her dildo. She loved sticking her finger up my ass while we played and even tried to fuck me with her dildo.
It seemed like I had the best of two worlds. As long as I wore lingerie Laura would let me do most anything too her and Ralph loved getting blowjobs from me while I wore it. I never did tell him that I enjoyed it more than he did.
Apparently Paul and Laura broke up as I didn't see him with her any more, but did run into him at a store in town at which time he told me he enjoyed the blow job and anytime I wanted to finish it to let him know. Which I took him up on.
About a year later I left to attend college and by the time I came back at then end of the first year they had all moved away. But I was now hooked and had to find other outlets for my needs.