tagFirst TimeFirst Taste of Sex

First Taste of Sex


I was eighteen the first time I made love to a woman, and I was lucky enough for it to be with my best friend. Her name was Anna, and we had known each other practically since birth. Through the years I watched her blossom into a beautiful young woman, and I had spent plenty of time fantasizing about having sex with her.

Anna was a year and a half older than me, and she stood a petite 5'3" tall. She was perfect: not too thin, but not the least bit heavy, with large 34DD breasts which hung perfectly when she went without a bra. She had long, soft brown hair which stopped just above her captivating ass. To me she was the image of the perfect woman.

I was a husky, 5'8" tall and weighing a tad under two-hundred pounds. With shaggy brown hair and blue eyes I wasn't the best looking guy out there, but I was handsome enough to hold my own. In my mind, however, I didn't think I ever had a chance with a woman like Anna.

It was early summer and school was out. I had just finished my senior year of high school, and would be starting college the following September. Anna had just finished her freshman year of college and would be beginning her sophomore year in the fall. Throughout June Anna and I had taken to swimming together, either in her pool or mine. Seeing her in her bikini was at time more than I could take, and she had occasionally taken notice of the bulge in my swim trunks.

In response, she had taken to teasing me, making sure that she brushed her breasts against me, hugging me in the pool so that our crotches were in direct contact. I had no clue at the time, but she was letting me know that she wanted me. For an entire month this little game went on, leaving me incredibly frustrated and I had shot many a load of cum into the toilet wishing it was into her.

Fourth of July weekend was the worst. Her parents had a barbecue and all the kids, Anna and I included were enjoying the pool. Later in the evening, only the two of us were left and Anna decided that I should wrap my arms around her from behind, because she was cold. I did what was asked of me, and placed my arms around her stomach, and bent my knees so she would have somewhere to sit. The coldness of the water was enough to keep me from having an erection, so there was no awkwardness to the embrace. That was until two events took place: First Anna began to grind her ass against my crotch. This began to make me hard, but I was able to move my body in such a way so that my stiffening cock wouldn't be noticed by her.

Then Anna took my hands and cupped them over her breasts. I tried to pull them away since her parents were just inside the house, but she put her hands over mine. I could feel her hard nipples through the wet fabric of her bikini and immediately got the hardest erection of my short life. My cock poked her in the ass cheek, which made her giggle. It was incredibly hot, yet awkward and I was relieved when the party was over and Anna's parents kicked everyone out.

For the next few weeks this teasing continued, but Anna got more and more aggressive. She had taken to changing into her bikini in front of me, with her back to me so that I could catch the occasional glimpse of her pussy lips. She had also began to untie her bikini top, allowing the sheer mass of her breasts to hold it in place, leaving very little to the imagination. It was driving me nuts, but I was afraid of what could happen if I told her I enjoyed her teasing as much as she seemed to enjoy being a tease.

In late July I guess Anna couldn't take my lack of action anymore and became very assertive. We were both in her bedroom alone, playing some video games. We were in our bathing suits waiting for some thunderstorms to pass before we could go swimming. Anna asked me to go downstairs and get some sodas, since her parents hated it when she traipsed about in her bikini. When I stood up, she knelt in front of me, pulled down my swim trunks and put my still flaccid dick in her mouth: she was giving me my first blowjob!

I was shocked, but my cock seemed to know what was going on, as it quickly hardened in response to the attention it was receiving. Anna continued to suck my shaft, paying attention to the head with her tongue. She caressed my balls with her hands and looked up at me the entire time. Soon I couldn't take it anymore and I felt myself reach the point to no return. I warned Anna, and she began to bob her head as I filled her pretty mouth with my spunk and rode out the most intense orgasm I had ever felt. I was already weak in the knees, but I was nearly floored when she opened her mouth to show me the sperm inside it and I was further shocked when she swallowed my cum.

After standing up, Anna kissed me on the cheek and proceeded to take off her bikini top and bottom; she was now completely naked. I stared at her, taking in the beauty of her body: her large tits with their eraser sized nipples and light pink aureole (which also stood up as she became aroused), her perfect ass and her glistening pussy which had blossomed like a flower. She layed on her bed, on her back and spread her legs. My cock, which had begun to soften after the blowjob, now sprung back to attention at the sight of Anna's pussy lips, and the insertion of her fingers into her wet hole.

She put her fingers in her mouth, tasting her juices, then looked at me and motioned for me to come to her. I complied and she said "make love to me, I want your cock deep inside of me, and I don't want to wait anymore." I was once again stunned and at first refused, being concerned since her parents were home and we had no condoms. Anna put my fears to bed replying: "They're in the basement, so as long as we're quiet they won't hear a thing." I once again asked about protection, not wanting to become a parent in my teens, to which she replied: "Don't worry, I've been on the pill since last summer, now will you please stop worrying and just fuck me!"

With that I mounted her missionary style. I put my cock between her pussy lips and teased her by sliding it up and down from her erect clitoris to her tiny pink asshole. This had the effect of making her squirm and giggle and culminated with her demanding that I penetrate her. I stopped my teasing and placed the head of my cock between her pussy lips, right at the entrance of her vagina. I could see and feel just how wet she was, and could smell her wonderful musky aroma. With one slow motion I thrust my cock inside her, burying myself to the balls in her snatch.

The feeling was overwhelming, her pussy was hot, wet and felt like velvet; it was the best thing I had ever felt. Since Anna had sucked me off earlier, it took a few minutes of thrusting before I had the urge to cum. Anna must have felt my cock twitch and harden further, because she looked into my eyes and said: "That's right baby, I want you to cum deep inside my pussy." It was her words that finally pushed me over the edge, and I felt my balls tighten as I shot spurt after spurt of hot jizz into her, having a quite intense orgasm.

The long, deep thrusts which preceded my ejaculation must have sent Anna over the edge, because I felt her body tense and her pussy rhythmically contract around my quivering member. After or orgasms, which seemed to last forever, I pulled my softening dick from her vagina and watched as Anna began to push my semen out of her. It was a beautiful sight: her young, freshly fucked pussy dripping with cum. She giggled and said: "A creampie, just like in the movies."

The thunderstorms never moved on, so we spent the rest of the day having sex over and over, until we were both too sore to continue. Anna confided in me that I was not her first time, but that she had wanted to fuck me for quite some time. We spent the next two years having sex whenever we could, which was often since we only lived a few blocks apart. It was with Anna that I learned how to eat pussy, where the G-spot is and had my first experience with anal. I miss her dearly and am eternally grateful for all that she taught me.

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