My Hot First Time Part II

On the drive home, I couldn’t believe what had just happened. All I could think of was Caleb…the feel of his lips, the taste of his skin, the feeling of his penis as it exploded in my mouth, the image of mine as it slid into his beautiful round ass, and look in his eyes when he told me he loved me. I felt like years had passed in one afternoon, but I had no idea what any of it meant. There was a part of me that felt impending shame, and some fear about whether or not I would ever see him again, but the afterglow was still so strong that it barely registered. Not long after I got home, I was sitting on my couch looking around the room. It was the same old room, but somehow everything seemed to have changed. The phone rang. I cleared my throat in an effort to sound as normal as I could before answering, “Hello?”

“You forgot the pictures.” It was Caleb’s voice with a slight sexualized teasing tone. I tried to sound disappointed, even though I was absolutely electrified at the knowledge that I would see him again. I made a plan to go back and get them the next afternoon. For some reason, as soon as we hung up, I was terrified. What if it was awkward? What if slept on it and regretted it? What if I did?...What if I didn’t? What if I was…..

I played it cool with my girlfriend. She never suspected a thing, and I didn’t tell her I was going back there the next day. I had a terrible time falling asleep that night. The next day, I wore jeans that were a little baggier, and underneath them I put on a pair of my girlfriend’s panties. They were tight, and it felt a little funny walking out to the car. Maybe I did it to hold down any possible erection, or maybe to feel some measure of control over the situation. I suppose there could have been other reasons. The entire drive over there, I became more and more afraid. By the time I rang his doorbell, I could feel a hand around my throat. Footsteps from inside…my knees began to wobble.

When the door swung open, our grinning eyes met for just a second, then we both looked away and smothered our smiles. We greeted each other somewhat curtly and he led me to the basement where he’d left the flash drive with the pictures on it. I felt like he was trying to rush me out of there, or rush me downstairs, and I’m not sure which one scared me more. I followed him. He was wearing grey sweatpants and a white t-shirt…as though I wasn’t even coming…what did that mean? When we got to the basement, he handed me the flash drive without saying anything. I stood there for a moment, expecting something more.

When it became clear that he was trying to rush me out, I began to shift my weight to turn around to leave when he said, “I heard a great song the other day and got the CD, do you want to hear it?” I said yes, and he told me to go push play on the CD player. It was one of those big ones set into wall shelfing, and I couldn’t find the buttons. “How do you work this thing?” I asked.
He came up behind me. As he reached his arm past me to point, his chest brushed up against my back. I was immediately filled with the feeling I had the previous day of losing control. “Which one?” I asked.

“Right here,” he replied, as he moved to push the button himself. He pressed up against me more fully, and I could feel that his boner was unrestrained by his sweatpants as it brushed against the inner part of my right butt cheek. As we both stood in that position, I heard the beginning of the song ‘Bittersweet Symphony’ for the first time. We were both frozen. I pretended to shift my weight to the other foot, but I was actually brushing my butt across his pulsing bulge. I felt his hand on my hip as he began to kiss my neck. I melted. I soft “okay” was all I could manage.

He nudged me onto the large bed in the main room, and came down gently on top of me, kissing me firmly and passionately, without any of the hesitancy of the day before. As the song began to grow, we began to dry hump each other in time to the music as our tongues danced like a pair of conductors. Our constrained penises rubbed against one another, and our hands moved all over as though they knew by memory where to go and had been yearning to go there for years. I grabbed his ass and held him to me. He reached down and pulled his shirt off, and I eagerly pulled off mine as well. I could see the top of his boxers for a second before his warm skin seemed to cover me completely. I could feel his treasure trail brushing mine as our bodies undulated.

He shifted to one side and began to clutch at my top button. I suddenly remembered that I was wearing my girlfriend’s panties, and as the little red hearts on a white background emerged, complete with a large wet spot on the front, he laughed slyly. “Did you tell your girlfriend about yesterday?” he asked. “Um…no.” “Yeah.” He said with a grin as he moved down and began to kiss my stomach. His hand reached down the front of my panties, and gently pulled out my cock, bending it over the white cotton. “It’s your turn” he said, just before his warm mouth enveloped me. This was unlike anything any girl had ever done to me. He moved his lips up and down, sliding his tongue around at just the right times and places. He sucked my dick like it wasn’t a foreign object, but something he understood. The song started over again on repeat. “Oh my God, Caleb…you are so good at this.”

I could feel his breath on my stomach, and his lips popping just a little on the rim of the head with each vertical move of his head. I placed my open hand on the center of his back and tried to watch him, but the pleasure was so intense that I kept falling backwards. My lips went numb, and I began to feel warm all over. He began to stroke my balls through the panties gently with his fingertips, each caress starting from further and further down. I began to moan, and lift my butt up off the bed to meet him. His hand began to slide along the edge of my panties, gliding just a tiny bit underneath the edge. I knew what he was trying to do, and moaned “yes” in non-committal approval which could be taken as permission to touch my hole or just enjoyment of the best blowjob I had ever had.

He took the hint and I lifted my knees and spread my legs a bit as his fingers slid toward my ass. When he touched my hole, a jolt of electricity shot up my body and I moaned uncontrollably. “Caleb, I’m going to cum soon” I said, and he stopped sucking me. He made direct eye contact with me and said softly, “it’s your turn.” “Okay,” I replied. He left my shining penis poking out of the panties now partially soaked with pre-cum and his saliva, pressed against my stomach and leaking slowly into my treasure trail. As he took a position directly over me, I lifted my legs and spread them to present him with access to my opening. He pushed the panties to one side, and began to place his warm dick against my hole. He looked right at me.

The song started over again, maybe for the third or the thirtieth time…I had completely lost track. As he started to apply pressure, I realized that he wasn’t just going to slide in. I was suddenly terrified. I was going to have to relax…I was going to have to LET him into me. Something about that was scarier than anything I had ever known. I looked up at him, and his big brown eyes beamed down at me with a look that said it all…I realized that he had let me into him the day before, and that when he’d told me he loved me, this is what it meant. I nodded and said “Okay.”

I saw his stomach muscles begin to work as he applied pressure, and slowly began to part me and slide in. It was starting to hurt, and it kept getting wider. It felt like he must be miles into me, but we just stared into eachother’s eyes. I’m sure mine screamed, ‘I’m scared and it kind of hurts.’ His seemed to say, ‘it’s okay’ over and over again.

Suddenly the tip of his penis passed the tight rim of my hole, and he seemed to punch through a barrier. In one instant I moaned almost in surprise, and he moaned in incredible pleasure. He looked so hot fucking me. His hands pinned mine to the bed, and his abs pulsated as he slid slowly in and out. I felt like I was flying, like gravity had been a lie all along. I could feel every detail of his gorgeous dick sliding past my insides, ending at a point of intense pleasure before retreating again like the waves of the ocean. I bit my lip, then opened my mouth wide without thinking about it. I began to moan a little with every breath. He reached down and wrapped his hand around my leaking manhood, panties irregardless. “I still love you, Skyler….yesterday wasn’t a mistake.”

“Caleb…” I knew but I couldn’t say it. I substituted, “I love you too.” I could tell that this felt good for him. He was bigger than he had been at first, and he began to sweat, get red, and breathe. I got used to the feeling of pressure down there, and found that it felt better than anything I had experienced. I began to moan, and that moaning grew louder and more intense as his penis kept filling and refilling me and his hands caressed my dick like they had done it a million times before. I was sweaty, and breathing so much that I felt light headed. My moaning went up gradually in pitch until it sounded at least as effeminate as his had the day before.

There I was, covered in sweat, wearing hearted panties, moaning like a girl with a young man jerking me, while his glistening body pinned me to the bed as he fucked me in the ass…but I was loving everything about it. I couldn’t believe the sounds I was making were coming from me. I began to beg him…”Caleb, don’t stop…don’t you dare stop…fuck me, Caleb…fuck me like you love me.” Then I said it; “I’m gay…Caleb, I’m gay…I’m gay and I love you and I never want this to end, I love you, Caleb.” He looked down at me like he was too close to cumming to speak, but a tear ran down his cheek as he pounded and convulsed on top of me. His hand began to jerk me frantically, and I kept squealing.

Suddenly I felt his dick inside of me jump and he froze, but shook slightly as he stared directly at me with is mouth wide open, a single tear clinging to his chin. Another jump, and I could feel his warm semen inside of me. Another jump, this one more violent and suddenly I was cumming too. As he pulsated into me over and over again, my own cum laid itself across my stomach, squirted onto my chest, and shot onto my face, a large dollop landing on the side of my mouth. As his hot cum filled me up and the pulsations subsided, he fell down onto me, breathing heavily. Our sweaty bodies pressed together, and he put his arm around me and kissed the cum off the side of my mouth. He pulled out, and his semen poured out of my ass, soaking into my girlfriend’s panties. The song was still playing.

“Skyler, is this real?” he asked. As we held each other.
“I think I’m in love with you, Caleb.”
“Me too.”

We made a plan for the next afternoon, and I went home. I never told her, but I broke up with my girlfriend that night.