I've bee lurking GWS for awhile now and I think it's time I catalog my experiences here as well. All you need to know about me is that I'm currently middle aged and while I'm not an Adonis, I'm attractive enough to have gotten all the pussy (and occasionally dick) that I've had. I've seen many a story here about girls losing their virginity, but hardly any about a guy's first time. So that's where I'm going to start.
I was what you might call a late bloomer (at least by today's standards). I had my first girlfriend, let's call her Amanda, at 18. She was my age as well, but vastly more experienced as I would come to discover. She was a very petite girl, standing only 4' 11" and probably 100 lbs soaking wet. She had no chest to speak of, but she did have a nice, tight little butt. She had a slender face and long raven black hair. But what really got me were her eyes. Big, blue and round just like any Pixar character you'be ever seen. I could get lost looking into them.
I won't bore you with the details of how we met or ended up dating. We can skip right to the end of our third date. I'm sitting in my car getting the first blowjob of my life and I was loving it. Later on, I realized her technique wasn't all that great, but the one thing that made her blowjobs memorable was when she would look up at me with those beautiful blues with her lips wrapped around my cock. That first time, that was all it took for me to cum. Even, without warning, she managed to swallow it down.
As I drove her home that evening, she told me how horny she got from sucking me off and pulled a small vibrator from her purse. Do you have any idea how hard it is to drive straight while a girl is masturbating in your passenger seat?! The fact that I got us both to her house alive was a miracle. As I pull up to her house, she moans, "Circle the block a few times, I'm almost there." Two laps around the block later, she orgasms quietly, then pulls her panties off from under her skirt and hands them to me as a "souvenir". I drove home that night thinking that I had been grossly misinformed on what the activities of a date entailed. It didn't really dawn on me that my new girlfriend was a budding sex addict.
Less than a week later, she had me sneak into her room after our date. It wasn't very hard, her family was dysfunctional enough that her parents never checked on her and spent most of their time in front of the TV on the other side of the house. She sat me down on her bed and told me to wait there as she disappeared into her closet.
I knew what was eventually coming so I shucked my shoes and jeans in preparation for what was to come. She reappeared in a sheer red teddy and matching thong. I've never been as rock hard as I was at that moment. She smiled devilishly at me and pranced over to straddle my bulge. "I'm glad you approve. I've been so horny all night thinking about your cock. I hope you don't mind skipping the foreplay, but I need your dick in me bad." She wasted no time in pulling my cock out through my boxer briefs and positioned it at her pussy lips. I didn't have time to object if I had wanted to (I didn't) before I felt the velvety tight walls of her pussy envelop the first 3" of my cock. She squealed, then said exasperatedly, "You're much thicker than my last boyfriend." Now, I'm fairly average in my opinion, but it was still quite the confidence boost.
She stated bouncing up and down on me, working my cock deeper into her gloriously wet pussy with every thrust. I rested my hands on her hips and enjoyed the view. As you might suspect from my debut performance in the sexual arena, things ended quickly. Her final thrust to impale herself on me fully was enough to make me climax, and I pumped my load deep in her pussy.
At this point rational me was having a panic attack, thinking I had just knocked Amanda up, but rational me was currently being drowned out by dick-in-a-tight-pussy me, who was clearly in control of my decisions at the moment. As I would find out later, she was on the pill.
Amanda looked down at me with her big blue eyes and said, "Oh, you came already? Guess you got those first time jitters out of the way. don't worry, I'll fix you right up." Suddenly, I felt her cunt flex, squeezing my cock. She repeated this several more times until my cock was at full mast again. I've only been with one other girl who could flex like that, and if you've never experienced it, you are seriously missing out.
She continued riding me for a few minutes before requesting we change positions. We moved to missionary from there, which made me feel powerful and in charge when she wrapped her legs around me. I pounded her hard once I got my rhythm going. I'm not sure how long we fucked like that until I blew a second load into her.
As we laid on the bed catching our breath, I kept telling her how amazing it was. She smiled coyly at me and said, " oh, just you wait." Then she licked my cock clean before I left.
Source: reddit.com/r/gonewildstories/comments/3crivi/the_start_of_my_sexual_life
I thought this was a great story! Please write more. :)