A Female Sailing Instructor

I've written a couple stories on here, and met quite a few people on-line. Some of the most interesting stories and conversations are about real life experiences. I have decided to tell about a few of my own. Of course the names are changed to protect the guilty, but the story is true about how I lost my virginity.

I was raised as a good Catholic boy. I actually went to an all boys Catholic High School and of course was taught all the horrible consequences of things like masturbation and goodness forbid pre-marital sex. Thanks to that early education, I can now be counted among the many cheating, sex craved men in this world. So, it wasn't until I was 18, about and leave for college that I finally lost my virginity.

All through my childhood, I had enjoyed sailing, it was an activity I enjoyed with the family and we were members of a local "yacht club". I had graduated from being in a sailing camp-type program to teaching at one in a neighboring harbor. One weekday evening, my hometown yacht club was hosting a party associated with a local junior regatta. In the early 80's where I grew up, legal drinking age was 18, and it wasn't thought of as a horrible breach of morals to let the sailing instructors drink alcohol while the junior sailors had a dance. By around 10:00 it was time for the dance to end and the juniors to get to bed. One of the instructors at my parents yacht club had had a few too many and was in no shape to drive home. B. was a few years older, 21 at the time, which to 18 year old about to head off to college seemed like an eternity of years. She had also been my sailing instructor for a few years previously. My gracious parents offered to put her up in our house for the night. As luck would have it, she was offered my room and I was going to sleep on the pull out couch in the basement.

Before going to bed, I took a walk into the back yard and noticed that B. was standing out on the porch off my room. We chatted from ground level and I climbed up the side of the house so we could chat on the porch itself. After a few minutes of idle chitchat, I decided this was my big chance … as any awkward teen-ager might do, I put an arm around her and we began to kiss. Twenty years later, I can't say that I remember the kiss, but I sure remember the rest of the evening.

After some grouping in the night air, we slipped into my room. Just inside the door, I continued kissing B. and groping at her breasts. B. was one of those women who really had breasts that were too big. Not a skinny woman, but in decent shape, her breasts must have been EE or some outrageous size. Previously, I had dated nice girls from the Catholic girls school and of course they were all practically flat chested. I had also never done more than get a hand under a shirt for a feel, and hand under a skirt for a feel down there. My knowledge of sex was what I had learned from reading issues of penthouse forum and a copy of some classic erotic novels.

After fumbling with B.s bra, I finally had her breasts out in the open, I was sucking on them like a baby and B started to moan. At the same time, I had a hand down her shorts and I was trying to get those off. She helped me out and I soon had a finger up inside her. We were still standing, with me awkwardly bent over sucking a breast with a hand in her pussy. B. pulled me over to the bed and I quickly pulled my tee shirt and shorts off my body. It's hard to believe I dodn't cum just doing this much, but I had managed to hold off.

I wanted to try everything at once, so the first thing I did after kissing again for a while was to spin around and go down on B in a 69. B. I do remember the smell and taste of it … I'm sure B hadn't planned for me, she had spent a day on the water likely sweating and getting a bit "stale" between the legs. I didn't really know better, but I do remember how pungent the odor was. She had a full bush of hair, and I was running my tongue trough it tasting pussy for the first time. B. hardly had my cock in her mouth before instinct took over there. I began trusting my hips into her and after two strokes realized I was about to cum. I quickly pulled out. I don't remember if I thought I was being nice pulling out of her mouth so as not to cum on her, or if I was too interested in putting it in her and didn't want to cum so quickly. Either way, I spun myself around and got between her legs.

I remember quite clearly how I slipped right into her. Definitely beginners luck, because I often to this day have a tougher time finding the right spot, the right angle, etc. It's no surprise to me now that after two stroked inside her pussy I was ready to cum again. I wasn't smart enough to ask if I could cum inside her and I wasn't wearing a condom (this was before aids, and I wasn't aware of the Herpes threat) so I pulled out and came on her belly. At that point, I knew she hadn't cum, and I was determined to be a half decent lover, even if I had just had a premature ejaculation. So, I went down on her again, almost immediately.

At this point, her musk was a lot lighter than it had been the first time, and I discovered what many others know. 69 isn't all that great a position for oral sex. In this position, I had a better idea of what was where, and I could move around a lot more freely. I started to eat her out as best I could. I didn't dive in and try and bury my tongue in her pussy, I was sort of hesitant and just licked up and down on the outside. In hindsight, I probably came across as a great pussy eater since I'm pretty sure I was ticking her clit on the upstrokes. B. was moaning and enjoying the attention I was giving her. She reached down, grabed my hand that was at her side and started to grip me. I'm sure she came at that point, and I was SO damn proud of myself.

After B.s muscles relaxed, she pulled me up next to her again. We kissed and giggled, there was still a lot of awkwardness. I was paranoid that my parents might hear something. I tried to get out of bed, but B. told me to stay for a minute.

We kissed some more and she reached down to my cock, it was still hard, and she let out a Mmmmmm sound as she pulled me on top of her again. This time, she placed my cock where it had to be and wrapped her legs around my back. She told me to just hold still and she started to grind against me. I remember trying to "pump" and she kept saying no, just hold still. I am not very big, 6" or so and I started wondering what was happening, she wasn't letting me "fuck" her like I thought it was supposed to be done, and thought that was because I was too small and she thought I would fall out. Of course I know realize, she was enjoying grinding her clit against me while I was deep inside, something that can be a lot more pleasurable than the "in and out" especially if it was making me last a little longer. I case you thought this was turning into a geek becomes sexual dynamo story, rest assured, it didn't happen that way.

As soon as B started to get more into it and build the pace of her grinding, I was about to cum again. She knew what was happening, and I tried to pull out, but B. said, "it's okay, I'm on the pill". Seconds later, I came inside her. She was still doing a slow grind on me and moaning softly … kissing me telling me that felt great. Once again, fear kicked in. I was paranoid my parents would hear something, and go looking for me.

What a dumb shit I was, I'm sure B. would have enjoyed fucking well into the night, and at 18, I could have easily cum many, many times. For years afterward, I thought I had never given away my virginity, in hindsight, I'm sure she knew, and if she didn't know I was a virgin, she sure knew I was new to it!

Just in case you STILL think this is a geek turned stud story, I did what any 18 year old would do in this situation. I ran the other way in the morning. Despite being on cloud nine all day, I didn't know what to do about B. After all, I had had sex with her, that probably meant I should marry her! So, I avoided her like the plague. She even asked me out to a movie later that week, and I declined "I'm kind of seeing someone" I lied. Instead of finishing the summer with sex at every opportunity, I went back to my shy ways and fumbled around with awkward girls my age.

In college, the situation was just as bad, I wasn't a virgin, but for some reason, I still thought "good girls don't" and managed to go out with the women that didn't for close to a year! Eventually, I did find a few "bad girls" but got serious about one way too early, and now she is my wife, but I'll have to leave all that for another story.