[M]y [F]reshman Firsts | 2016

This is the story about my first real sexual experience, as is probably true with most it wasn't the best sex I've ever had, but it was one of the most memorable times. I've tried my best to tell this as it happened, awkwardness included. I hope you enjoy.

At the time of this story I was in really good shape. Around 6'5, 275.

I really didn't date much through high school, as my main focus was on grades and football (working really hard for a chance at a D-1 scholarship). I had one long term girlfriend who was pretty conservative and we really hadn't tried much of anything besides a few wandering hands during our 2 years of dating. By my senior year I was beginning to see my hard work pay off as several scholarship offers rolled in.

I chose to attend to large state university with a pretty good football program and prepared to head off to college. My girlfriend chose to attend a smaller school closer to home and despite the distance we decided we would try a long-distance relationship. . .

I moved away right after graduation and began classes and summer workouts. Now anyone who played college football will tell you, your first year is rough. I was too tired to party and I felt as though every second of my day was rescheduled. Not to mention trying to manage an LD relationship. I was physically and mentally pushed harder and farther than I could ever imagine that first summer, but its also the summer I met Jackie.

Jackie was one the tutors supplied to student athletes. She was a junior and a few years older than me. She was a petite girl at 5'2 and weighing somewhere around 110 lbs with shoulder length black hair and an olive completion. She wore a lot of workout gear, including these leggings that really accentuated her surprisingly full ass.

Anyway, I ended up being one of the only football player stupid enough to take physics so I ended up spending quite a bit of time alone with Jackie. During our study sessions we got to know each pretty well and as my relationship begin to crumble, Jackie and I grew closer. . .

On the few occasions I did hit the bars, she would end up joining us. We started grabbing lunch or coffee between classes and finding excuses to run into each other.

It all started pretty innocently. We went from sitting across the table from one another to setting side by side, I begin to notice her "accidental" brushes against my arm and her foot grazing grazing my leg. The sexual tension when Jackie was around was becoming palpable.

I was little embarrassed at being a virgin and the fact I hadn't really done much more than make-out up to this point, but during one our study sessions in the fall our conversations finally turned sexual, I let my inexperience slip and to my surprise Jackie's face lit up and a devilish grin slowly appeared on her face as her hand crept up my leg. She looked me in the eyes, biting her lower lip. . . . and said "that needs to change". She then moved her hand and started rubbing my cock and stroked me through my shorts a little. I asked Jackie where this was headed and she responded "where do you think?"

At this point my heart was racing and my cock was pulsing. I wanted to jump her right there and almost did, before realizing we were still in a glass enclosed study cube. We agreed that it was time to cut out and head somewhere more private.

After composing ourselves, and figuring out my dorm was occupied we headed to back to Jackie's apartment. By the time we made it to her car we were making out again and filling each other up. This only lasted a few minutes as someone came up.

Jackie pulled some FI moves as we sped back to her apartment. The minute her door was closed we were all over each other and our clothes were coming off, but then she suddenly stopped, pulled away and said "we are taking this next part slow because I want you to remember every detail" She stepped back, and led me to her room.

Once inside Jackie began running her hands up my torso and over my chest we made out for a few minutes, as my hands explored her amazing little frame and then in a single glorious motion her lips left mine and slowly began to venture down body until they reached my bulging cock. As she hit her knees Jackie began to explore every inch of cock from outside my shorts. She looked up at me smiling and licking the outside of my shorts . . . I can literally close my eyes to this day and remember the anticipation of this moment.

She then began to pull down my shorts and boxers, slowly exposing my cock until it eventually burst free. She giggled a little and under her breath I heard her say "Oh my god". I asked if everything was ok and with the biggest smile she said "oh yes!" With that commenced my first blowjob.

She slid her lips over the head giving it a slight kiss, before she began slowly licking the entire shaft from top to bottom. Her lips left the base of cock as she began kissing my balls and then she made her way back up my shaft. . . Suddenly she took the entire the head back into her mouth, but this time was different, she twirling her tongue as she went deeper. Her moans were getting louder. Ours eyes met and I had to use every ounce of strength I had not to cum at that very moment.

"Oh fuck Jackie"

She was worshiping my cock, stroking the base while rubbing by balls. It was amazing and this went on for what felt like forever (in reality I'm pretty sure I didn't even last 5 min) And then it happened, I tried to pull away "I'm about to cum", but Jackie shook her head and wouldn't let go. When it hit me I became so weak in the knees I almost collapsed, my balls tightened up, my cock had swollen up and the pulsing deep within had intensified to a point I couldn't take it anymore.

I began shoot load after load and Jackie was taking every bit, it kept cumming and cumming, until finally the spurts began to subsided. The look on her face was pure satisfaction as a little cum leaked out the side of that championship smile!

With that continued smile she stood up, grabbed my cock and gave it an ever so gently tug as she backed up to the foot of her bed. As she backed up I help Jackie remove her top, exposing her amazing her perky c-cup tits. At this I lost all control and carried her the last few steps, throwing her on the bed and tearing her leggings as we tried to remove them as quickly as possible.

Over the next hour or so we spent making out and exploring each others bodies and talking. Jackie whispered in my ear, "What should we do now". I said "I want to give you something" as I began to position myself toward the end of the bed. I slowly began to make my way, ever so slowly, down Jackie's perfect little body, sucking and kissing every inch of my journey until I finally reached my destination.

My first taste of pussy was amazing, it was something like a bland sweetness as I kissed it for the first time, but the moment itself is what made it. I looked up at Jackie from between her legs and she asked what It thought. . .(I was nervous as hell, because I didn't have a fucking clue what I was doing at this point.) I wish I could say I responded with a smooth line and dove into her pussy providing immediate satisfaction, but I didn't, instead I asked her what she wanted me to do from there.

Jackie, smiled and said "you are a perfectionist aren't you!" She gave me ever so detailed instructions guiding me at times with her finger. After a little guidance I felt comfortable enough to go it alone and began licking her wetness working my tongue in her inner lips and blowing slightly on it. She began to lightly thrust herself into me more as went and her moans grew louder. "You're a fast lear . . . . oh fuck baby right there" She was furiously rubbing her clitorus as I dove a deeper sucking and licking her lips. Her thrust became quicker and harder until she finally let long exhale and said "Oh. . . my. . . god"

Once again we lay there talking, making out, and continued to explore. It was an already an incredible evening and I was still technically still a virgin, but we both had a pretty good idea of what was coming next.

Earlier that evening during some of our exploring we had already tired to slide my into her, only to find it was going to take a little more work than expected. . . This was horrifying at first, but Jackie was quick to let me know that all this meant was we get to have a little bit more fun than usually.

After much playing she rolled over on top of me, grabs my shoulders, and begins to rub her soaking wet pussy over my now throbbing cock. She looks me straight in the eyes and says "I'm ready, are you?" I give her the nod of approval. She re-positions herself and her pussy slowly begins to envelope my cock. Now this is where inexperience gets the better of me as I decide now in moment of absolute bliss that now is a good time to throw a couple "porn thrusts" into the mix. . . Jackie screams "shit! are you trying to kill me" as she digs her fingernails into my shoulders.

I'm mortified by this, and we have to take a quick break to make sure everything is ok. Once I get the all clear that devilish smile appears again and I'm told "I guess I'll just have to teach you everything" We decide that it would probably be best to go at missionary style this time around.

With me on top, Jackie slowly guides my cock between those tight warm lips once again until I'm completely in. She lays there for a moment, her eyes closed and a slight grimace on her face. She repositions herself just a little pulling away and then pushing back down on my cock. The grimace begins to fade into a look of pure pleasure. She finally opens her eyes, giving me the sexiest look. I slowly begin to pump into her, as she grabs my forearms. As her moans intensify she says "Fuck me" "Fuck me harder". Her pussy began to clamp down on my cock as I finally hit a rhythm and I felt a wave of electricity suddenly working its way though my body, I was about to cum and there was no stopping it. (Not sure I even broke the 5 min barrier here either) Before I had a chance to even think about pulling out rope after rope of cum was unleashed inside her. Jackie is half giggling "holding her head saying "yes fucking yes" as I fill her with my cum (yes, she was on the pill).

Once I finish, I pull out and collapse beside her. "Wow" I said. Suddenly Jackie rolls back on top me, and holds both hands up. . . I lay there not quite knowing what to do, until she says "its double high five time". We high five and laugh for minute. Jackie excuses herself to go clean up and leaves me laying on the bed in all my glory. So many things were running through my mind, and I just smiled.

This was just the beginning of a very fun time in my life with many more experiences! Jackie and I ended up dating on and off for several years.