My True Diary of Sexual Firsts: Volume 2


Less than five minutes after merging onto the secluded Trace from I-20, Brandi had my khacki cargo shorts unzipped and her tiny fingers wrapped around my growing manhood. Due to the incredible lack of private locations available to a fifteen year-old boy and his fourteen year-old girlfriend, manual sex while driving had become one of our consistent rituals and one of the main reasons that I looked forward to making the hour-long drive to the springs. I struggled to maintain a steady course as her cold, little hands worked their magic up and down my shaft. She broke contact only for a quick moment in order to spit into her palm, just like I had taught her, and returned to much more frictionless handjob. By now, in fact, Brandi was quite the little handjob professional. She had become enamored with watching me ejaculate, and I dare say that she was a little obsessed with making it happen. We rarely kissed anymore for longer than twenty or thirty seconds before her fingers would travel about my midsection to locate her favorite plaything. Public, private, semi-secluded-- none of those details mattered much to her, as she claimed that the thrill of possibly getting caught made her want to try it even more. I must say that I agreed, but I guess I am just a more naturally cautious person. For instance, the week before this very trip, she had convinced me to sit on the back row of our church's balcony so that she could masturbate me during the boring sermon, but I had trouble maintaining an erection or reaching climax with my parents sitting only a few rows ahead. None of that mattered now, though, as we were completely alone and inside of our comfortable element. Brandi stroked me with long, slow motions from hilt to head, while massaging my scrotum with her other hand. Only moments later I was swerving from lane to lane while releasing a massive load of cum onto the already previously-stained steering wheel and dash. As was usual for her, Brandi scooped up some of the wads of my warm nectar and dribbled it onto her tongue and swallowed. She cooed happily, kissed my cheek, and settled back into her seat, apparently contented with it all. We rode along the highway in silence for the next several minutes, and my mind began to wander.

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   I pondered the incredible difference between a dry handjob and a wet one. I considered how Brandi seemingly enjoyed tasting my cum, and I even thought back to times when she had leaned in closely in order to observe my orgasms up close. I was young, ignorant, and naive, but I was at least reasonable enough to realize at that very moment that altering only a few small details in our little ritual would change nice handjobs into virgin blowjobs. I resolved to delicately raise the suggestion. "Uh, Brandi. . . " I began, nervously. "Are you happy with our relationship?""Sure I am," she replied while nonchalantly studying her fingernails. "No, seriously. I mean, are you truly happy? Like, could you just keep doing this for the rest of your life?" I stammered. "I think we're a bit young to start discussing marriage," she remarked, sarcastically. Yet, now I at least had her full attention. "Oh, I know. What I mean is that.


  . . er. . . don't you think that we should consider taking our situation to the next level?"She thought for a moment and replied, "Well, yeah, I guess so. Am I getting boring to you?""No, of course not," I said, emphatically. "I just think that there are, like, worlds of other things that we could try, and I never really liked anyone well enough before to want to suggest that. "It was a poor execution of a brilliant ploy-- to tie her in by making her feel unique and special before revealing my idea. My tact was certainly not completely developed by this point in my life, but I got the job done. Her interest was now piqued, and her expression, serious. "Well, what did you have in mind?" she finally mustered. "Sex?""No. . .

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  . er. . . I mean, yes. Well, I mean, I would love to, someday, but not until we both feel ready, you know? I was really thinking of something else," I continued. "You know how you kind of like the taste of cum and all, so I was sort of hoping that you might want to try making me cum by using your mouth. " I can still to this day feel the intensity of my surprise when she started giggling at the level of anxiety with which I muttered those words. "You mean that you want me to go down on you, right? You want a blowjob. " she said, patronizing me playfully. I was embarrassed but at the same time relieved to know that I wasn't suggesting something foreign to which she had given no prior consideration. Apparently her sister, who was two years older than me, had explained to her quite in detail about oral sex and perhaps other things as well. I nodded affirmatively and waited anxiously to hear a reply. Brandi sat thoughtfully silent for some time and then explained that she would have to consider it for a while before being sure. I told her that I was in no rush, though I secretly wished she had been a little more receptive.

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   Touching my penis had been an act of pure curiosity for her, but the idea of moving ahead to more serious acts seemed to come across somewhat fearfully. However, that latter thought could not have been farther from the truth, as I would soon find out. We arrived at Rocky Springs only a few minutes later and found the other two cars in our party already waiting. We found out that Clint had not been able to get his hands on any beer but instead had swiped a few bottles of cheap wine from his dad's wine cellar. Everyone gathered the various blankets, bags, coolers, and other gear, and we set out to find a shaded spot near the water that would lend both privacy and space. Settling in, I was able to take a good look at everyone who showed up. Clint was a seventeen year-old guy who lived up the street from me and with whom I had spent many an afternoon skateboarding. His girlfriend Amy had also come along, a shapely tenth-grader in a white knit swimsuit cover-up and bright green flip-flops. Then there was Stacy, Brandi's sexy little best friend. At around 5'4" and maybe 110lbs, she was easily the curviest of the group. Her little blue swimsuit top could barely contain what were already probably C-cup breasts. I gasped inwardly at the sight of her cleavage, a quality not yet bestowed on most of the girls I knew. At Brandi's request, Stacy caught a ride down to the springs with John and Kelly, two other friends of ours and the last two in the group. John and Kelly had been friends for years, but there was never any romantic attraction between them. I never truly understood why not, as Kelly was a ninth-grade soccer player with dark hair, a great tan, and easily the most athetic body of anyone that I knew.

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   For years--as I became more sexually active--would I wonder about how amazing she must be in bed with her rock-hard calves and tiny, tight ass. (The story of how I eventually found out is another entire story in itself. )The four girls immediately stripped away any superfluous coverings and went straight for the water. Kelly stretched out a blanket to sunbathe while Brandi, Stacy, and Amy went for a swim. John, Clint, and I took our shirts off and decided to break out the wine. None of us were very experienced drinkers, so only a few sips of the potent wine had us already feeling pretty good. Momentarily, the girls came back to join us, and we all ate and drank wine, talking and laughing and telling stories for what seemed like hours. The boombox was tuned to a decent Top 40 station and played along in the background. I was seated in a folding lawn chair with Brandi sitting below me on the blanket, leaning against my legs. I played with her hair as I drank, and her left hand was massaging my ankle and calf behind her. She had not put back on her shorts when the swimming was over, and I often stared down at her long, creamy legs. In fact, the view of her in conjunction with that of the other girls had my penis sporting a half-staff stiffness within my shorts. Brandi turned herself slightly as the conversation continued, and she began to more effectively rub my leg, moving closer and closer to my thigh. It was easy to tell that everyone was getting a quite drunk, as the subject of discussion kept returning to sexual and semi-sexual themes. Soon, we were all telling stories and asking truth-or-dare style questions of each other.

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   As we all laughed at an obviously fabricated blowjob story that John was telling, Brandi suddenly stood up and stammered to gain her balance. All of our attention went to her, and after finally curbing her drunken giggles, she began to speak. "Everyone, I have an announcement to make," she began, slurring most of her syllables amongst intermittent snickers. "We're all close friends here, so I wanted to ask your opinions about something. " She continued, "On the way down to the springs today, right after what I thought was one of my best handjobs, David asked if I would suck his dick!"I turned immediately red at her candor, and slithered down in my seat, refusing to make eye contact with anyone in the group. Everyone else laughed and cheered as Brandi went on. "I wasn't sure that I wanted to do it, but I have decided just now that I will. And I am going to do it right now!!" she proclaimed. The party bursted into applause and whistles, and Brandi began to move erotically to the music as if doing a strip tease.
    The group, unsure as to whether or not she were really serious or either unafraid if she were, cheered her on. I sat there blushing in my chair, watching Brandi's little ass sway from side to side in front of face. Her tiny, low-cut bikini bottoms were French-cut and left very little to the imagination. Then she turned to me in time with the music, fell to her knees, and began rolling her neck in a way that made her long, straight blonde hair twist about my chest and stomach. She reached up and unzipped my shorts slowly, freeing immediately my raging erection. I was now seated in front of four girls and two guys with my now 8" cock standing at full attention, out in the open for everyone to see.

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       As it popped out, the cheers and catcalls made a harsh crescendo; the girls were shouting remarks about my size, and the guys took turns pretending to spank Brandi's tiny ass. Brandi stroked me a few times in long, deliberate motion, leaned back and downed the last gulps of her wine, and then wrapped her warm, wet lips around the head of my dick. With that, the others each got up and gathered in a small circle around us. Brandi's right hand continued to stroke my shaft and she sucked with reckless abandon on the tip. Now completely lost in the moment, I wrapped my hand around her head and began to guide her mouth toward an in-and-out motion. She caught on quickly and began to move her head on her own, taking more and more of the length of my cock into her hot mouth with each pass. The others got in on the act as well, barking out commands to her as she worked. "Use your tongue!" Kelly shouted, and Brandi responded by stopping her motion and flicking her tongue in super quick motions back and forth across the underside of my shaft. Stacy, Brandi's best friend, got down on her knees next to Brandi to get a closer look. She put her arm around Brandi and rubbed her back gently as Brandi responded to more and more commands. The whole scenario was too much for me. I was getting my very first amazing blow job in front of all these people, and the pressure began to build with little warning. I announced in between moans that I was about to cum, and someone in the group started chanting, encouraging Brandi to "swallow, swallow!" Brandi was slurping away with incredible fervor at this point, and I shouted out as I began blasting stream after stream into the back of her virgin throat. She swallowed quickly the first few shots but pulled away from my cock as she did. Still stroking it in fast motion with her hand, the next blasts fired in every direction.

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       At least one hit Brandi in the face, some landed on Stacy's bare shoulder and arm, and still others found their way to Kelly's swimsuit top and neck. I must have blown what felt like at least a pint of steaming cum, and the group laughed hysterically at the strange conclusion to what was an even stranger spontaneous event. The girls giggled as Brandi apologized and tried to find something with which to wipe the stray shots of jism from her friends, and the guys congratulated me on a job well done. A long time passed before the group regained its full composure. In fact, after everyone seemed to have finally settled back down, we all relapsed into hysteria again when Stacy found another gob of my cum on her stomach. Brandi said that she would handle it and surprised everyone by leaning down and licking off the leftover nectar. She responded to the catcalls by kissing Stacy on the cheek, saying that best friends could share anything. After several more hours of talking and swimming, we boys finally felt sober enough to make the long drive home. We all gathered our things, said our goodbyes, and loaded the vehicles to head home. When finally in private again, I kissed Brandi deeply and thanked her for taking our relationship to the next level. She assured me that she was sorry for her drunken boldness but was glad that we were closer now than ever before. Yet, this relationship that had so far been built on so many firsts and so many surprises still had many more of both in store. .