High School Sweethearts

Published 4 years ago

I lived in a log cabin with a huge fireplace and even larger windows. The view from the windows was fantastic; it looked out over open fields bordered by deep woods. I lived in the middle of nowhere, and I liked it like that. The only thing that peeped in my windows was the occasional deer that wandered into my yard. I rarely wore clothes around the house, in the summer or winter. The fireplace kept the house way to hot in the winter. During the summer, I just like to feel the cool breeze across my naked body. But tonight I had some skimpy shorts and a tank top on; because my old high school sweetheart was coming over for a visit. The call came out of the blue; I was stunned for a moment when Danny started talking. After all, I hadn't seen or heard from Danny in about 15 years. We had always had a good friendship, but it just wasn't there when it came to sex. We talked for a while, and by the end of the phone call you would have thought we had just seen each other yesterday. I had given up on dating, I never married, I just couldn't find a man that satisfied me. I had even tried women, but that didn't take either. It was fun, the sex was adventurous but it just didn't seem to satisfy me. I didn't have any major faults, other than I liked living alone. I wasn't bad looking and I kept my self fit and trim. So, I had relinquished myself to being single and masturbation. It wasn't a bad life and I could have sex anytime I wanted, with no hassles. Over the years I had acquired quite the sex toy collection. I had vibrators, dildos, even a strap on harness from my "lesbian" days.


I saw Danny's car lights shine across the snow covered meadow as he drove up the hill to my cabin. I little flutter swept through me, and I thought to myself, "Quit be silly your acting like a little girl." I had been in an very cheerful mood all day, thinking about Danny. So much so, that I had fucked myself with my favorite vibrator for hours. I layed against a pillow on the floor so I could watch myself fucking my pussy in the huge wall mirror. Danny knocked on the door and I opened it with a grin on my face. Holding up a bottle of brandy, he said, "Peace offering." I couldn't figure out quite what he meant by that, so I just snatched the bottle and said "Peace." I led Danny into the cabin and gave him a little tour. We ended up in front of the fireplace, I said, "Sit, I'll get some glasses and we'll open this bottle." I returned with two glasses and Danny opened the bottle. Pouring the brandy he said, "You look terrific, I can't believe you're not married." With a sigh I replied, "Just doesn't seem to work for me." After several glasses of brandy we both were getting a little drunk. Danny said he should be going before he had to much to drink. "You can stay here and sleep on the couch if you would like to," I said. "Well, if you think it would be OK? I'm really having a great time and didn't want to leave so soon," he said. "Sure, no problem Danny. I'm enjoying this too, it's been so long since we've seen each other." I got up to put another log on the fire and Danny said "You're going to roast me out, I didn't dress for the warmth of your fire." Bending over to stoke the fire, I playfully wiggled my ass. My shorts were of the "short-shorts" variety and I knew my ass cheeks were in full view, I said "House rules, if you're hot, get nekid." "Don't tempt me," Danny said. "Tempt? I'm not tempting you, I'm daring you!" I replied. The brandy and seeing Danny had gotten to me. I was horny and it had been a long time since I had been with anyone. "I never have been able to refuse a dare," Danny said. He stood up and stripped completely. He still had a good body also, the years hadn't been hard on Danny at all. When I gave him the once over, there was one thing I noticed that was hard, his cock. Danny had always been self conscious about his dick. He thought it was little. It wasn't, but it wasn't big either, just an average size cock. This was fine by me, I had no size preference really. If anything, I liked the average size best. "Hmm, I can't be having my company be the only naked person in the house," so I stripped my clothes off also. I saw a look of appreciation on Danny's face as I sat next to him. We enjoyed some more brandy and soon the conversation turned to sex. I asked Danny what was wildest thing he ever did. To my dismay he told me he had never really done anything wild. "It was always just your basic sex with every woman, I guess that's why I never got married," Danny said. "Okay, what's your wildest fantasy?" I asked. A look of bold determination came over Danny's face. He sat there in silence for quite some time. I could tell he was struggling with something that had been on his mind for a long, long time. I gave him a few minutes and then said, "Danny, we are both adults, I don't think you can say anything that is going to shock me." He sighed and shook his head, then he looked straight into my eyes and said, "I want to know what it feels like to be fucked in the ass. But I'm not gay, I don't have the slightest inclination to have sex with a man." Danny and I had experimented with anal sex in high school. In fact we had more anal sex than regular sex. We hardly ever had condoms and I was scared I would get pregnant. So I would let him fuck me in the ass while he played with my clit. We both would get off and I never got pregnant. We stared at each other for a few minutes. He did shock me, I thought I had heard, seen, and done it all. "I knew I shouldn't have said anything," Danny said. He started to get up. I touched his shoulder tenderly, "Sit Danny, it's OK. I just needed a minute to take that statement in," I replied. As he sat back down, I swung over him, straddling him. I took his face in my hands, looked him in the eye and said, "If it was anyone but you Danny, I would probably not do anything. But it is you, and I've always cared about you. How long have you felt this way?" Danny looked at me and said the second shocking statement of the night, "Ever since the first time you let me fuck you in the ass." Now it all came together. Now I understood why it never worked out for us. He needed something from me and never said what he needed. I never knew before, and that's why it seemed like I could never satisfy him completely. I kissed him, a deep loving kiss that said more than words could say at that moment. "Don't go anywhere," I said as I broke of the kiss. I rose from the couch, reaching between Danny's legs and stroked his now soft cock for a moment. Then I quickly ran up to the loft bedroom. I looked through the closet for a minute, finding what I wanted. It still fit just right, and I went back downstairs. Danny was still sitting on the couch, his brandy glass upturned in his mouth. I stepped in front of him and he almost choked on his drink when he saw me. I stood there, with my strap on harness fastened to my waste. I dildo protruding from my pubic mound just above my pussy. I had a bottle of anal lube in my hand. I knelt down in front of Danny. I bent forward, never saying a word to him. I took his cock in my mouth. It was soft, I slowly sucked on his dick. I felt it start to grow in my mouth. Cupping his balls I lifted them slightly and with my other hand I spread some anal lube on Danny's asshole. I kept sucking his cock as I worked the lube into his ass. I felt Danny's hips rise a little. I slipped my finger into his asshole. It was so tight, I started to worry that the dildo I was wearing would be way to big to fit in him. A moan escaped Danny's lips as I fingered his butt. I sucked his cock in time with my finger going in and out of his asshole. Danny's was moaning in pleasure, he seemed to be taking my finger more easily. I spread a bunch of that anal lube on my dildo. Stroking it on, it felt so good in my hand. I was getting really turned on. With a loud pop I withdrew my mouth from Danny's now throbbing cock.


I pulled Danny's hips to the edge of the couch. I pushed the dildo towards him, touching it against his asshole. "Yes, yes," he moaned, "Fuck me in the ass." His cock stood straight up, throbbing as if ready to explode. I pushed my hips into him. A little at time until I finally got the head of the dildo in his ass. I halted a moment, letting him get used to it. Then I started to pump my hips. Each thrust took that dildo a little deeper. Soon I was fucking him. Danny met each of my thrusts with a look of love in his eyes. We never spoke except for the occasional moan and groan of pleasure. As I buried the dildo in his ass, the harness would press against my clit; sending shudders of pleasure through me. I started fucking him faster, I was almost to the brink of an orgasm. The look in Danny's eyes, the harness rubbing my clit, that dildo going in and out of his asshole. It was all I could take. I grabbed his cock and started stroking it. My hand wrapped tightly around his shaft. I felt his cock expanding in my hand. I reached around my thigh with my other hand. I slipped a finger into my pussy through the access hole in the harness. This was all I could take, a gush of girl cum squirted from me. I screamed as I started cumming. Squirting all over the floor, I kept stroking Danny's cock and fucking his ass. I looked down just as Danny came. The years of frustration powered his cum. I had never seen a man squirt like Danny was doing. The cum gushed from the head of his cock straight into the air. I bent my head forward and opened my mouth. Catching some of his cum in my mouth. Most of it hit me in the face, but I didn't care. I finally was giving Danny something he wanted and needed. After all these years I finally felt what I was missing. From the look in Danny's eyes I knew we had both found something special. I eased the dildo from Danny's ass and leaned forward. My belly pressing down on his softening cock, the dildo pushed between his ass cheeks. We kissed, a long deep loving kiss. I rested my head on his chest and whispered "I love you, Danny." Kissing the top of my head, he said "I've always loved you Jenna."



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