(F)irst of many young escapades | 2016

So a little background first, when I was 18 I was in love with the guy who took my virginity who I naively thought I was going to marry. I moved from the Midwest, out to Arizona for him because he played baseball, but pretty soon I found out that not only was he cheating in me, but he was on an epic rampage of pussy and was fucking every girl on campus. Again I was young, and hurt and confused and alone in a city where I knew very few people. All I knew was that I would have my revenge, and I started out with the baseball team. Before I confronted my boyfriend Josh about cheating, I wanted to have sex with his teammate Jose because they both played he same position and had been competing for playing time, and I had always had a thing for Latin guys but had never been with one before. I wasnt quite sure on how to seduce a man at that point in my life, so at a house party where we were all at I got pretty drunk and just started flirting with Jose a lot, touching him and hoping he'd get the hint. Josh was with his friends at the same party and had all but forgotten me so I was totally focused on getting Jose away from the party. I was feeling confident, partly because of the cheap beer but also because I had recently started a new birth control pill and it had the added side effect of growing my boobs from 34b to solid 34c. I hadn't had a chance to get new bras to hold my swollen twins so I stuffed them into a bright pink VS push-up which was now hanging on for dear life. I had also chosen my tightest fitting Capri dress which was slightly sheer as to really let the link bra show through. I asked Jose to be my beer pong partner, and he agreed but only for one game because he wanted to leave early. I turned my flirting on to full blast and I could tell he was turned on by all of my attention, but he wasn't the aggressive type and just kept sneaking looks at my body when he thought I wasn't looking. I had been touching his arms and his back all night, and had even brushed my overflowing tits on him multiple times but he still didn't do anything. Finally after the game Jose said he was leaving and I felt like a failure, but as a last ditch effort and since I wasn't going home with Josh I asked Jose to give me a lift to my apartment and he agreed. We hopped in his oversized Jeep and as soon as we started driving I grabbed at his cock and he was completely shocked, but didn't tell me to stop. I stroked him softly, and his bulge was starting to stretch the limits of his jeans. I unbuckled my seatbelt and leaned over the console and used both hands to unzip his pants and pull out his semi hard dick.
Now it was my turn to be shocked, as even in its semi flaccid state his dick was at least twice the size of Josh's average cock. I had never been with a Hispanic guy at this point, so I was also surprised at how dark his dick was, at least twice as dark as his tanned body. I took the head of his chocolate monster into my mouth and felt it begin to grow immediately. I licked it softly a few times and then plunged it as deep into my mouth as I could go and I immediately had a gag reflex. My eyes watered and saliva came rushing out of my mouth but I continued to suck as Jose struggled to drive. I thought I was good at head with Josh as I could take him all the way into my throat, but with Jose I was now using both hands to stroke his shaft and the head was still 3 inches on top of that. His cock had to be 9 inches and at this point was rock hard. I wanted suck him off and be done, but no matter how hard I tried I couldn't get him to cum. Finally we end up at my apartment parking lot, and Jose asks if we want to continue inside. My jaw and throat are completely worn out at this point, but instead of inviting him inside I pulled my dress over my head and straddled him and his monster cock. The sheer dress I had worn was one that required me to go without panties and after 20 minutes of deep throating a giant, my pussy was dripping wet. I began grinding on his dick, my pussy juices blending with my saliva already on his cock. He unhooks my bra and my tits come bursting out, nipples hard and he sucks one and roughly grabs the other with his hand. I continue to work my hips and pull Jose's shirt over his head. He has a beautifully tanned body, but was not completely sculpted and ripped like Josh, a little soft and chubby but still surprisingly hot and he had unbelievably smooth, hairless skin. His hands were rough and calloused, and as he squeezed one tit with his right hand, he squeezed my ass with the other. He was ungodly strong, his hands pinching and squeezing my body I felt a pain and pleasure I had never felt before. As he squeezed my ass I felt a finger touch the bottom of my pussy, ever so slightly entering me but not completely fingering me. He would touch my pussy, get one finger wet and then rub the area between my ass and my pussy gently but with increasing pressure. I continued to grind the top of my pussy and clit drenched in juices while he teased my taint with his rough finger until he began to rub my asshole. Almost instantaneously my first orgasm erupted, my breathing ragged and Jose was furiously rubbing my ass, his finger just barely entering my hole. My legs were shaking and as I recovered I could feel Jose's soft and muscular chest lift me up as he positioned his monster cock at the entrance of my quivering vagina. As he lowered my body onto his dick I could feel his girth filling me up and stretching me out in ways I had never felt before. The combination of his size and my post orgasm sensitivity was too much and all I could feel was pain, but the pleasure of getting back at Josh kept me from stopping Jose. Slowly my body adapted to Jose's dick, and while his thickness now felt good, his overwhelming length was still too much for my lithe 5'7 125 lb frame. He continued to try to go balls deep inside me, but couldn't get it all the way in. Nonetheless we got into our groove, me bouncing on his dick, but never letting it bottom out and hurting me. I loved him sucking on my nipples while he lightly fingered my asshole, but the excruciating pain of him stretching me out ruined any more chance of me cumming again so I leaned back against the steering wheel and let him watch my body go to work on his cock. I gave him a show; I squeezed my nipple with my right hand and rubbed my clit with my left, and I moaned softly every time his giant cock pulsated into me. He had seemingly endless endurance, but I could tell my show was working and he was getting close, so I leaned forward a bit and told him to fuck me harder. I put both of my hands on his chest, and felt him grab both of my ass cheeks and almost ripped them apart. He began to pump furiously, now bottoming out with every stroke, each thrust felt like it was punching my cervix with a club. The pain was intolerable, but instead of telling him to stop I screamed as if it was in pleasure and encouraged him to finish. It felt like an eternity, but finally I could tell he was about to cum and as he rammed his monster cock into me balls deep, I could feel the pulse of cum rise up from his balls. He tried to hold me tight, to blast his full load deep inside, he had an iron grip on my ass holding me firm. But somehow I wriggled free, only allowing the first rope of cum inside me, the remaining three or four ropes squirting out onto his completely soaked jeans. Before he had a chance to fully recover, I had my dress back on and was out of his Jeep, staggering to my apartment. I left the bra, a token of my past sex life, one that I had truly outgrown.