Here’s another installment of the ghosts of hookups past! I met Dan in college, he was a year or two younger and whenever we were at a party together we always seemed to gravitate towards each other, inevitably winding up in a corner kissing. It all seemed pretty innocent; he was a very passionate kisser, but I noticed he kept his hands respectfully on my waist or at the small of my back. I was at the point of college where I was hooking up with so many jerks, I was surprised to meet such a gentleman, and I found him to be overwhelmingly sweet. He looked at me with stars in his eyes….so I figured I had to ruin him.
One night me and my roommates were throwing a rager at our house. We had a buddy bring his DJ equipment, a damn-near fully stocked bar, and we were all dressed in next to nothing. I had opted for a black T-shirt dress that was mesh, showing off my lace lingerie set underneath (a conservative choice compared to many of my friends), my long red and purple hair worn down extra curly. I had cleaned my room, certain that even if Dan turned me down, SOMEONE would end up in bed with me. When Dan got to the party, we found each other immediately and our game of cat and mouse began.
We ended up outside in the backyard, drunk and smoking a joint (really me smoking it, Dan took a puff to be polite), where I finally blurted out that I wanted him and asked him to go upstairs to my room with me. He grinned before letting out a shaky sigh and saying, “Okay, listen. There’s nothing I want more than to be in your bed, but before we go I have to tell you….I’m a virgin.”
“Really?!” I giggled, before realizing it may be a sensitive subject for him. “I don’t mean to laugh, I’m just surprised! You’re a really good kisser.”
“Well I’ve done SOME stuff,” he said, “I’ve gotten head, and done some hand stuff, I’ve just never took it much further. Hanging out with you, I finally feel ready…I just don’t want to disappoint you by not being any good. I don’t know what I’m doing.” He looked down sheepishly, as if afraid to meet my gaze. It grew quiet between us and we listened to the music blasting from inside. I hadn’t been with a virgin since my high school sweetheart, who I lost my virginity to. I remember it being a pretty bad experience, neither of us knew what we were doing…but I sure knew now. I realized that I was able to make his first time actually good if I played my cards right. I felt my cheeks getting hot with excitement and pulled his face to mine for a deep kiss.
“Well I’m going to teach you how tonight. I hope your ready to be an obedient student for me.” I giggled, “give me ten minutes and then come up to my room alone.” He grinned and I slipped inside. I turned to run up the stairs away from the party, my heart beating out of my chest, but turned back and grabbed a bottle of bourbon on my way up and took a long pull from it.
SEX PART STARTS HERE
Dan entered my room and stood there nervously, but his eyes were devouring me. I had stripped down to just my black lingerie set; a lace bra and thong, but I had also switched to my sluttiest highest heels(I figured they’d be hot to keep on). Even with the heels on, he still had at least a foot on me as I closed the space between us, pulled his shirt off and ordered him to take a seat at the desk I had in the corner of my room. I could see the bulge straining against his pants, and i made sure to run my hands over it as I knelt down in front of him. He lifted his hips from the seat for me to pull his pants and boxer briefs down so I could finally wrap my lips around his cock. It wasn’t too thick, but was very long and it had the perfect upward curve. I licked up the whole length of it before looking him in the eyes while sucking lightly on the tip.
As soon as I started sucking his cock, he began moaning loudly. I’m glad the music was still playing at the party, because he was even louder than me, and I am pretty loud in bed! I Rolled my tongue around the head of his cock before sinking the length down my throat. He moaned “oh fuck..you are so beautiful. Mmmm, you’re so fucking beautiful with my dick in your mouth”. I chuckled and rolled my eyes, he was really so sweet but I wanted to be a whore not a princess that night. I forced him to hold my hair back, allowing him to steer and push my head down to swallow his cock. I started to deepthroat him, gagging loudly when he hit the back of my throat, to his absolute joy. He reached down to rip my bra cups down to expose and fondle my full tits.
I decided to switch it up, especially since I wanted to make sure he didn’t cum too soon. I moved him from my desk chair to sit on my bed and straddled his lap, allowing my tits to fall right at his face. He opened his mouth and found one of my hard nipples, sucking on it as his hands wandered all over my body. I felt my panties get wet, I loved that he wasn’t trying to be the respectful guy I hung out with at parties. He was now part feral animal, moaning and undulating his hips beneath me. His cock was sliding against me, and for a minute we were just kissing and grinding to the beat of the music a few floors below us.
“Are you ready to learn how to fuck me?” I asked.
“Please teach me!” He groaned against my mouth.
“First you have to make sure my pussy is ready for your big cock. I want you to make me cum before I let your cock inside of me.”
He needed no further invitation. He flipped me onto my back and his face disappeared between my thighs before I felt his fingers pull my panties to the side to show him my hungry pink pussy. I felt his tongue start to lick me, but it was clear he didn’t know exactly where to go. I started directing him with my voice and hands; pulling him by the hair until his mouth found my clit, guiding his fingers to push inside of me and curl against my g-spot. He took direction well, and before long he was sucking on my clit and gradually picking up speed with his fingers, forcing me to buck my hips against him and moan his name. With a small warning, I came hard on his face, and he pulled away slick with my juices and laughing excitedly. He was so proud of himself, but I could tell he was a little nervous for what was next.
I finally slid off my panties, now soaked, and straddled him again, allowing him to lay down while I rubbed my dripping wet pussy against him to keep him hard, letting just the tip in before rolling my hips away. I could feel him try to lift his hips up to go deeper, but I kept teasing him.
“I know we should wear a condom, “I moaned, “but I want you to feel every inch of your dick sink inside of me for the first time. Do you promise to be extra careful not to cum inside of me, please Dan?” He nodded vigorously to my question as I continued to ride the head of his cock, clearly desperate to lose his virginity completely raw. He moaned and grabbed my hips to try and force them down further but I wouldn’t let him. I started bouncing on the end of his dick a little faster, still just riding the first 3 inches or so to tease him. A few minutes of this had him struggling, between moans he started begging me to fuck him. I could feel how wet I was from controlling his pleasure, my tight pussy needed to feel his cock deep inside now, I couldn’t wait another second. I plunged myself down to take his full length, making him cry out and throw his head back. Then I rocked my hips slowly while riding him, taking my time. His eyes were rolling in the back of his head as he moaned my name, and seeing his intense pleasure amplified my own. I pulled his hand down and helped his thumb find my clit so every rock of my hips put pressure on it to bring me another orgasm. I could feel my cum dripping out of me onto his legs and running down his balls. Without even asking, he pushed me over onto my hands and knees and got behind me, pushing his cock back inside of me with a shuddering moan of ecstasy. I wanted to push my head in the pillows and let him fuck me to death, but I didn’t want to lose the control I had over him just yet so I made him stay still while I twerked against him. With every bounce my nice fat ass made his dick would thrust into me deeper, and he was so dickmatized he couldn’t do anything but grunt and periodically slap my ass to watch it jiggle more for a good twenty minutes! I was surprised he was lasting so long, in my experience men usually can’t fuck me doggy style without busting quick (it’s usually a ‘finisher’). I think he was riding some virgin adrenaline that made him last longer-I wasn’t complaining!
“Now show me what you’ve been taught” I ordered.
To my joy, he picked me up and flipped me on my back (I was low-key exhausted, we’d been fucking for almost 2 hours by then), and soon he was holding my legs up by the heels of my stilettos, pumping his cock as quickly as he could inside of me, his eyes closed tight as he lost himself to pleasure. “Yes, fuck this tight little pussy, Dan. Make it yours. Your cock feels so good.” I moaned loudly for him. His cock really was perfectly curved for me, every thrust at this angle hit my g-spot and before long I was cumming so hard my vision blacked out momentarily. “Oh fuck yes,” he cried, “I can feel you cumming on my dick right now. You’re so. Fucking. Hot!” He said, and I could hear the strain in his voice. He was about to cum…but he wasn’t stopping to pull out. “Wait,” I heard my voice weakly call out, “don’t cum inside of me Dan”…but I was basking in the afterglow of my own orgasm so much so that I knew I couldn’t stop him.
He cried out with each rope of cum he shot inside of me, slamming his hips hard against me to bury his cock as deeply inside of me as he could. I felt him fill me up with his hot load, and he collapsed on top of me with his face buried in my neck. As his cock grew soft, he reluctantly pulled it out of me, but gasped and watched as his semen ran out of me and pooled on my sheets. “You promised you wouldn’t cum inside of me” I scolded him, but I have to admit that I wasn’t so mad, it was insanely hot feeling him have such a powerful explosion for his first time. “It was worth it. That was by far the best feeling I’ve ever had in my life.” He said with a loopy smile.
Then we fell asleep spooning for a little, waking up with the house quiet. The party ended hours ago. “You were a really great teacher, you know,” Dan murmured in my ear, “I’d like to review what I’ve just learned, if I’m allowed….” I felt his hard cock rub against me from behind me, “maybe I can earn some extra credit?”
Dan and I fucked for a few months after this, and he figured out how to pull out better; learning the joys of cumming on my face, my tits, my ass, my back, and all adjacent areas! He fell pretty hard for me, claiming he fell in love with me when I took his virginity, and unfortunately he got a little too clingy and jealous for my taste. After i broke it off, he apparently went off the rails for a little and inevitably dropped out of college a year or so after I graduated. Last I heard he had moved to the mountains. Wherever he is, I hope he’s making somebody cum as hard as he did for me, because he deserves to share that gift with the world!
Source: reddit.com/r/gonewildstories/comments/hs0z7x/fm_thinking_back_on_boyfriends_pastdan_the_virgin