Katie’s first time.
Katie and I had been friends since second grade. We lived in a small town and our families attended the same church. I guess it took me a while to realize it but Katie always had a thing for me. She would maneuver to be my lab mate in science classes, join the clubs I belonged to and even attended sports games when I was on the team. Being in a small town and because of our long friendship I never really thought much about it until in sixth grade when she asked me to a Sadie Hawkins Day dance. We started to look at ourselves as boyfriend and girlfriend as we knew each other so well. This moved into going “steady” in High School and naturally our sexual relationship grew. By our junior year my hormones were raging, as were Katie’s, but we struggled to keep them in control. We would do homework together in her parents family room downstairs and soon it always ended in petting. Before long I was fondling her breasts and she seemed to like it. I worked my way into slipping my hands under her top and into her bra. I remember the excitement I felt when she let me unhook her bra and fondle her tits directly for the first time. Strangely Katie had one boob slightly but noticibly larger than the other due to a surgical procedure as a child but that did not bother me. Katie was fairly tall at 5’8″, 120 pounds with dark blonde hair pulled back in a pony tail most of the time and brown eyes. All the guys felt she had a nice body and was pretty in a girl-next-door sense. Her parents were fairly well off as her father owned a company and she had a younger sister with learning difficulties that they doted over. They had a nice house in the best part of town with lots of property and privacy. They trusted Katie completely and had known me forever so our relationship and time together never bothered them. They told Katie the trusted us and seemingly had no concerns when we were together. That trust led to a lot of masturbation for me.
As Katie and I moved into our senior year of High School our heavy petting grew more frequent and intense. Katie would now let me go so far as to remove her top and bra and even unbutton her slacks to allow better access to massage her ass checks. The first time I did this and squeezed her tits I shot a load in my pants. Katie laughed and felt honored that she had caused that. She offered to remove her slacks, which she did. She had nothing on but her panties. We necked and I could feel my hard penis against the head of her pussy through the panties. I came again I my shorts. I was out of control! We got to the point where we often both stripped down to just our underpants and kissed and fondled each other all over until we climaxed. Later one night when we were like this Katie asked if I would like to come back to the laundry room with her. Curious to what she had in mind I agreed. She said she had told her Mom she would start a load of wash before coming upstairs. She did start a load, creating washing machine noise to cover any other sounds. She then spread a bunch of soon to-be-washed clothes on the floor and we lay down. She asked if I would like to remove her panties for the first time, which she knew I did. After doing so she then reached over and pulled down my jockey shorts. We were totally nude. She bent over and gently kissed my rock hard member, licking it lightly. I explored her tits, pussy and ass with my hands. She let me insert a finger in her hot, wet pussy and probe it gently. She then took stiff my penis in her hand and slowly stroked it. She was obviously fascinated with it. Almost immediately I exploded all over her chest. She swirled her finger through the warm cum around her nipples for several seconds. She closed her eyes soon and I expected she was having her own climax. After several minutes of this she grabbed a dirty towel and wiped herself down and then me. I dressed quickly and left as our curfew time had arrived.
Our sexual relationship really reached its peak one Friday later that year when Katie told me her Mom and Dad were taking her sister to a visit a possible live-in school for the sister in another town. They would not be home that night and she had been entrusted to take care of her self that night. Katie asked if I would like to come over and she would make dinner. I readily accepted. I told my Mom I was going out with the guys and might be home late as it was a Friday. I arrived at Katie’s house that night in a driving rain storm. Katie had the garage door open so I could come through the breezeway and not get soaked. That also kept my car out of sight in the driveway from prying neighbors or folks driving by. She met me at the door with a deep French kiss and I got the sense tonight was going to be special. She was dressed in my favorite tight pink sweater and matching knit slacks, both flattering her young, nimble body. We watched a little TV and had a nice, if simple, steak and potato dinner. After cleaning up she invited me downstairs. There were no windows in the lower level family room so we always felt private there. We put on some music and began to kiss and fondle each other. We quickly undressed and were squirming around together on the couch. We were both hot and ready. She lay back and let me get between her legs. I licked the outside pussy lips several times and then slipped my tongue into her pussy repeatedly to moans of ecstasy and perceptible bucking from her. After several minutes of this she reached down and brought my stiff cock to the head of her pussy. I asked “are you sure?” and she nodded her head. She had been on the pill for a couple of months to help regulate her period so pregnancy was not an issue. I gently inserted the head of my cock into her virgin pussy and then pulled back. With each thrust I went deeper. She stiffened in pain and moaned quietly at first and then seemed to relax. I finally had my entire 6″ cock inside her. I tried to think of other things to prevent me from climaxing too soon but it was tough. As we moved in unison I sucked and tugged on first one nipple and then the other of her miss-matched tits. They turned me on! After just a few moments I felt her shudder and let out a soft groan. I came just as she finished her climax. We had our first sexual orgasm together and it was great. Within an hour we were back at it and each had our second orgasm. We sat naked and listened to music, fondling each others bodies freely and without restraint. It was getting late and I told Katie I had to leave. She said before I left she wanted me to do it with her one time but this time from behind. She got on all fours and I pushed my once again hard cock into her pussy while rubbing at her ass. I reached around for her tits and squeezed and tugged on her nipples as I pushed in an out. Katie came first, followed shortly afterward by me. We kissed, cleaned up and I went home, knowing there would be a lot more than that in the months to come.