Where it happened: On a boat off the coast of Maine
Langauge: English
Sex: Female
Rating: 5
Category: Straight
I lived in a rural town on the coast of Maine and it was near the end of my senior year in high school. I was finally getting out when I met Billy at a friend’s house. My friend’s name is Chuck. He wasn’t a boyfriend, just a friend. Bill was Chuck’s cousin from Boston. Bill was spending the summer and was going to work for Chuck’s dad to earn money for college.
Bill was nice, I liked him right away. So was Chuck, I guess it ran in the family. To me good looking is good, but nice is what counts. Billy was both. I could tell he felt the same about me. He couldn’t stop looking me over. First he’d look in my eyes, then his gaze would drop to my breasts, then I think he was embarrassed and he lowered his gaze even more but I was wearing a short skirt and so he’d look away, but then he’d look back and it began all over again. It was funny, him trying not to be too obvious, but I didn’t mind. He talked to me and seemed genuinely interested in knowing who I was, what I was doing in school, about my sister, and my parents. Maybe he was just being polite, but I don’t think so.
Billy asked me out on a date and I said yes right away. You should have seen him smile; I think he thought I was going to turn him down.
We went to the movies and held hands. He put his arm around me, but he was very respectful and didn’t try to touch me too far. I wished he would have, but I didn’t know how to tell him it was okay, but it didn’t take him too long before he did. We went swimming and the water in Maine is very icy, even in the summer. Mostly we cuddled and made out on a blanket out of the wind, but the sun was hot, and after a while we dashed into the water and stayed for as long as we could stand it, which wasn’t long. When we got out his eyes were glued to my nipples, which were advertising themselves quite nicely, not that there was anything I could or would have wanted to do about it. We got back under our blanket, he covered me up, untied my top and put my nipples in his mouth one after the other. Oh God I was beside myself. I never knew that sucking my nipples would be felt so right between my legs. I thought it was heaven, until he put his hand down between my legs and started exploring me with his fingers. Then I knew what heaven really was and it wasn’t long before I came.
I wanted him to come too, but it was too awkward, and too obvious, but I promised him another chance, and we went out almost every night and played with each as much as we could, which was a lot, but it was a long time before we really did it. I wanted to do it sooner, but I think he was shy, or insecure, and it took him awhile to get up the courage. Most guys aren’t like that, and even though I was really horny and didn’t want to wait I didn’t want to pressure him either. I didn’t like it when guys pressured me, trying to get into my pants, and I’d waited until I found someone I really liked, and I wasn’t going to rush him, but I was also worried he might never want to. Fortunately that didn’t happen.
On my birthday Billy borrowed Chuck’s dad’s boat. Billy’s dad also had a boat, a sailboat, and Billy was experienced. I think Chuck’s dad must have known what was going to happen out there, on the water, but Billy and I were both over eighteen and Chuck’s dad was cool. So was his mom. So were my parents for that matter, though I didn’t tell them I was going out on a boat alone with Billy for the day.
We went to a cove and anchored. It was sort of a lover’s lane for boat people. Very secluded, you couldn’t get there by land because of the cliffs, and it was sheltered so the boat wouldn’t rock too much. We went into the cabin and stripped right away. It was the first time we were completely naked together, and it was very private there and we could really relax and touch and look at each other. Billy was so hard he said it hurt. I said “here, let me sooth it for you,†and I lay on him and put him up inside me. It hurt a little, and it felt sore if he moved and I told him, and he tried to keep still, but the waves were rocking the boat and I was on top of Billy rocking right along with them with him hard up inside me. He couldn’t help himself and started in and out of me in short fast jerks, and that’s all it took. He came first, and I came a little later by pushing against him even though he got soft.
We ate and took a quick dip in the cold water, and in the afternoon he gave me a full body massage and we did it again. It took him much longer and I wasn’t as sore. It sure felt good.
Billy went away to college and we tried to keep up a relationship, seeing each other when we could, but the distance was too far and I fell in love with another man. I had to tell Billy, and I waited until I saw him in person to do so. It was one of the hardest things I ever had to do. Billy was nice, as always, and tried to make it easy on me though I could tell he was hurting badly.
The man I fell in love with turned out to be a bastard, and after I got married I got divorced. Billy got married too, and I knew he came around once in a while, visiting Chuck and his family, but I didn’t get to talk to him until he came up once alone and I made a point of cornering him in his motel room (in small towns everyone knows where everyone goes).
He was afraid of what I might do, he was right, and he didn’t want to let me in, but I was shameless and I teased him mercilessly in his doorway. I begged him to let me in to talk to him, and then I threw myself at him. It was mean. He really didn’t want to, well he didn’t and he did, but I begged him, and as usual he was too nice.
Afterward he told me that he wished, at least in part, that life had turned out differently, but he made it clear that it hadn’t. He said that what just happened would never happen again. I cried my eyes out thinking about how tenderly and lovingly he had just made love to me, and that I couldn’t have that ever again. I shouldn’t have done what I did, and neither should he, but the worst of it is that now I don’t know if he is the nicest man I ever met or the meanest.
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