Good Friends [f/m] (pretty long and a bit of backstory, sorry) | 2016

I had known "James" for a year prior to attending college. It had been a purely online relationship before then, and I was in a committed relationship with a long term boyfriend. However, that all changed when I found out that James was a senior at my new college. He was 5 years my senior at that point; I was at the very young age of 17 when we began to talk. Once I turned 18, I knew I could make the relationship sexual. We had met up once before, the little meeting ending with my hand firmly on his ass. From then on, we knew that we could never just be "good friends."

James was average height and relatively thin with a dark brown head of hair that matched his short, stubbly beard. On his nose lay a pair of thick-rimmed glasses, slightly crooked and broken, but that just added character. On the other hand, I am short (5'2"), thick girl. I have 36D breasts and an squishy hourglass figure with petite legs and feet. At the time, I had my hair dyed a radiant bright red that glimmered in the sunlight with a pinkish hue.

At the time of meeting, James and I were both dating different people, but we were both dissatisfied with our significant others. After one afternoon of sloppy sex in the backseat of his car, we both knew that we needed to exercise our "skills" in a different setting. James and I decided to attend a show in the city, and then I would sleep over at his apartment after it was over.

At the concert, I would feel James behind me as he gently rubbed up against my ass. I could feel his cock beginning to harden against me, and I responded by grinding harder into him. He let out a small gasp, and I peeked behind me with a knowing smirk. Even in the darkened room, I could see a tiny blush creeping over his face, and that inspired even more wetness in my panties. After two bands, we could not stand the sexual tension any more, so we decided to head home to his place.

Once we got to his apartment, I was very tired and decided to lie in his bed while he went to take a shower. Before I closed my eyes, I stripped off all my clothes and lay naked under his comforter. I was intending to surprise him when he pulled back the covers, but it would prove that I would be the one surprised once I fell asleep.

In my dreamy consciousness, I was half-awoken by minty lips pressed against mine. James had climbed on top of me and laced his fingers through my hair as he kissed deeply. He started gently biting my neck as he lightly traced his fingertips around my nipples, coming aggravatingly close to touching them, but he would not give me the pleasure just yet. As I was still waking up, he kissed down my body, lightly sucking my breasts and sliding a warm hand between my legs. He carefully began to massage the area around my clit, and I began to squirm. Suddenly, he pinned back my arms and began to lick my clit lightly but quickly and picked up the perfect rhythm. I felt myself nearing the edge of an orgasm before he released one of my arms so he could slide two fingers into my cunt, methodically fingering me and hitting my gspot with each movement. Finally, I came. I suddenly felt a foreign wetness between my legs and looked down to see James' face covered with it. He began lapping it all up on my thighs and pussy. Sensing I was confused, James kissed my lower stomach and chuckled.

"Have you ever squirted before?" he asked me as he began to stroke his cock. "No, this was my first time," I mumbled, embarrassed at my lack of experience. "That's so fucking hot," he murmured as he pulled me up from off my back.

He then pulled me onto his lap, roughly kissing me and scratching long marks up my back, making me moan with a mixture of pain and pleasure. As we kissed, I grabbed his thick cock and aligned myself with it. I slid down slowly as I lay my head on his shoulder, making sure I was taking every single inch and feeling him fill me up fuller than ever before. I bounced up and down on his cock for a while as he sucked on my nipples and rubbed my clit, bringing me to a few more toe curling orgasms. Unexpectedly, he hoisted me off his cock and pushed my face into the bed, my ass straight up. He spread open my ass cheeks and began to lick my asshole, his tongue darting into it as well as he slide four fingers into my pussy. I was begging for him to fill me up at that point, but he had plans that far exceeded my expectations.

He reached into the drawer next to him and pulled out a matte black butt plug. It was small, but I had never taken anything in my ass before. He squirted some lube onto it as he gently played with my pussy, cooing gently into my ear as he slid it in. I let out a moan when the entire plug was in me. After he called me his perfect little slut, he slid his cock into my pussy. The pressure of him fucking me also would move the buttplug ever-so-slightly with every thrust. Suddenly, I felt the most powerful orgasm spreading up my body. I felt the warmth travel on my skin, and I let out a scream as I gripped the sheets hard. I felt the now-familiar wetness drip down my inner thigh. Soon after I came, James grasped my hair into a ponytail and pulled hard, alerting me that he was about to cum. With one final thrust, he came deep into my pussy, staying in so I could feel his cock pumping me with more cum than I had ever felt before.

I was still on my hands and knees with the buttplug in as I felt my wetness mixed with his hot cum dripping down my thighs. James delicately pulled the plug out as he wiped a bit of our cum off my legs and brought it to my lips.

"Lick it up, slut," he instructed and kissed the small of my back.

I did as directed and licked it off his fingers, sucking hard. After one final slap to my ass, we snuggled into bed together and slept.

I wish I could say that we had any more intense experiences like this after. He ended up getting back together with his girlfriend a couple weeks after. I reconnected with him a couple months ago, but I was in a very happy relationship at the time and was not looking to re-ignite those old feelings. It feels nice to type this amazing night out again. I miss him often, but I'm pretty sure I just miss the great sex he would give me. Memories are a bitch sometimes.