Gabe's First Everything

"So, here's the thing. Gabe's never so much as kissed anyone before. He's kind of embarrassed about it. And he asked me if I thought you might be interested in maybe going out with him and, you know, helping him out with that." Anya giggled. "And I thought, well, you've mentioned that you think he's cute, and sweet, and... well, I figured I'd ask you, and if you think it could work, I'll ask if he wants to." She put her hands over her face. "This is ridiculous, isn't it? Arranging someone's first kiss?"

I tried to stifle a laugh, but my cheeks were burning. "He is sweet," I allowed. "But, wow, to be someone's first kiss - no, to PLAN to be someone's first kiss. That's kind of awkward. It's not like I have sooo much experience, you know."

"But would you at least maybe come to our suite party tomorrow and see where things take you? He said he wanted to come."

"Sure, I mean, I'll come to the party. Just...don't tell him I've agreed to kiss him. That would just make everything weird. Tell him I'll be there, I guess?"

Anya grinned. "Will do. Sorry if this was a completely ridiculous thing to ask you."

To be honest, I was kind of flattered, but it did seem like an odd thing to be doing, especially for a junior in college. Why couldn't he just ask me out? What was with the go-between? "No, that's okay." I lowered my voice. "He's really never kissed someone?"

"He's pretty shy," she said.

I nodded. "I'll be there," I said.

***

Gabe's arms around me are warm and comfortable. He kisses my mouth and down the side of my neck. I pull his face to my chest, and he reaches behind me to unhook my bra, then lifts my shirt off. I let my bra slide off my arms.

"Is this really your first time?" I ask, breathless.

"I've been dreaming of this for a long time," he says.

He kisses one breast and then the other, then continues his string of kisses down to the waistband of my jeans. He massages my breasts and rolls my nipples between his fingers. He returns to my lips and kisses me passionately while working the button and zipper of my jeans. I slip them off, then help him out of his shirt and pants. He lays me down reverently on his bed, studies my body, then lays down beside me, propped up on one elbow. He starts at the top again and works his way down, kissing my shoulders, my breasts, my stomach, then my inner thighs. He sucks on each big toe, then pushes my legs apart and touches my clit with one finger. I moan. He plays with my clit while sucking on my nipple.

"Please," I whisper.

He kisses me on the mouth again. I reach down to push at the waistband of his boxers, and he helps me take them off. I sit up and wrap my hand around his cock. It's big, much bigger than I expected, thick and hard and so ready. I curl around and take it into my mouth. He groans and grabs my hair in two fists. I move up and down, sucking and teasing with my tongue until he pushes me back.

"I'm ready," he says.

I lie back and open my legs. He guides himself into me slowly, savoring the moment. I feel him deep inside me. With a shudder and a cry, he pulls out, then plunges in again, faster. I rise to meet him. Just a few more strokes and I'll cum. I wrap my legs around his waist and pull him in, hugging him close. I need to feel his body against mine.

"Please," I say again, louder, and he pinches my nipple with one hand and kisses me again. "Yes, there!" I cry, and I cum hard, toes curling, my clit and pussy pulsing with release.

"Oh God!" he exclaims. With a strangled groan, he cums inside me and collapses atop me.

***

I awoke with a start, breathing hard. That was the most vivid sex dream I'd ever had. I'd really only had sex with one guy, and he hadn't been nearly as skilled as the Gabe of my dream. Our first time had been awkward and uncomfortable and it hadn't gotten much better the few more times we'd tried.

I wondered if Gabe really just wanted a first kiss or if had something else in mind. I had to get that dream out of my head before I saw him at the party or I wouldn't be able to face him!

The next evening, I showed up at Anya's suite with a slight case of the jitters. It felt like a huge responsibility, being someone's first - knowingly, purposely being someone's first. I had changed my outfit four times, put makeup on and washed most of it off, put my hair up and then brushed it out so it flowed gently around my shoulders. I'd finally ended up with what I hoped was a balance between "fuck me now" and "I'm your sweet girl next door" with a loose, red tank over tight jeans, my cute leather jacket, and boots with a low heel. My lips had a hint of color and my blue eyes were just a bit enhanced.

"You look so cute!" Anya exclaimed. Her three suitemates were scattered around their common room, each with a glass of wine. Anya's parties were no red-Solo-cup affairs.

"Who else is coming?" I asked, accepting a glass of white wine from her.

"Well, Gabe, obviously." She leaned in and whispered, "He's so nervous. But he was happy you said you'd come."

"Thanks, I think."

"No, he likes you. I think he thinks you're, you know, safe. Non-threatening."

"Ah." I was still not sure if that was a compliment or not.

"Anyway. He's bringing his roommate. What's his name? Jonah?"

I nodded.

"And I invited Kate and asked her to bring her suitemates, but I don't know exactly who'll be here."

"Cool." It sounded like a nice, sedate crowd. We'd sit around drinking wine and eating cheese, talk and laugh, and then? Was I supposed to take Gabe into Anya's bedroom and pounce on him? Was I supposed to invite him back to my room? Was I supposed to go up to his? How exactly did this work?

I sat in Anya's desk chair and crossed my ankles, trying to seem casual. I drank my first glass of wine pretty fast, though.

Gabe and Jonah came in a few minutes later. Gabe smiled nervously at me, then proceeded to sit across the room from me on the window seat with Jonah. He was wearing dress pants with a belt and a button-down, blue shirt. It was very...Gabe. He liked to look neat and professional. He refused a drink.

Great. I wouldn't even have him a little loosened up. I really had no idea how to approach this.

Anya went over to Gabe and Jonah and engaged them in conversation. I couldn't hear what they were saying, but soon Jonah got up and joined Anya on the rug. Anya caught my eye and tilted her head toward Gabe.

Wasn't this a silly little game we were playing! I got up and went over to the window seat. "Mind if I sit here?" I asked. I swallowed hard against a mad case of the giggles.

"Uh. Sure." He was not laughing. Or even smiling.

Now what? Make small talk? "Aren't you in Dr. Scherr's stats class?"

He nodded.

"I took that last semester. He's a pretty cool prof."

He nodded.

Oh my God, say something! "Um, you're a Soc major, right?"

He nodded.

I sighed. "Look, um, I know this is kind of awkward what Anya did. I want you to know that there's really no pressure. This is a party. We can just talk."

"I -" He cleared his throat. "I know." He scooted toward me an inch. "Can we go up to my room and talk? I feel conspicuous here. I'm not much of a party-goer."

I actually did kind of want to stay and join the party for a bit, but he looked so earnest and a little scared. He was cute. "Sure. Let me just say hi to a couple of people and tell Anya I'm leaving."

"Okay."

I saw Kate coming in with a few friends of hers I knew vaguely. Anya was sitting in a circle on the rug with Jonah and her suitemates, all laughing and talking around a spread of cheese and crackers. Anya looked up at me. "Go," she said, grinning widely.

I laughed. "You're crazy, you know that," I said. "Setting this up."

She just smirked at me.

I beckoned to Gabe. "Ready?" I asked.

"Uh." He cleared his throat. "Yeah. Sure."

His room was just upstairs from Anya's suite. We went inside and he offered me his desk chair. He sat in the other chair - Jonah's, I assumed - and scooted close enough to talk comfortably, but not close enough to touch easily.

"So, um," he started. "So," he said again.

"What would you like to do, Gabe?" I asked. I decided a direct approach was easiest.

He looked down at his hands, fiddled with a button on his shirt. "I like you," he said after a moment. It seemed like that was very hard for him to say. "And I'd like to spend some time with you." He didn't look at me.

"Sure, we can do that," I said. I rolled my chair a few inches closer to him, so our knees were almost touching, and leaned forward. I laid my hand on his knee. His eyes widened.

He cleared his throat.

"Do you want a drink or something to help you relax?" I asked.

He shook his head. "I don't drink."

Great, I thought. I had no idea where to start. "Tell me something about yourself," I said.

"I want to," he said. "I want to explain."

"Explain what?"

"Explain...what I want." He finally met my eyes. "I don't know...I don't know what to do with a girl," he said in a rush. He focused on my hand, resting gently on his knee. "I was raised in a very conservative, religious family. We didn't talk about... You know... Boys and girls." He pushed his chair away from me, out of my reach, and turned slightly so his side was toward me. His cheeks were red.

"I didn't know that." No wonder he seemed so nervous.

"No one does. I'm so embarrassed about it. People make jokes and I don't know what they mean, or I don't get the joke, or I don't even realize they're making a joke. People talk about...you know...and I can't even... I can't even pretend. So I just leave." He sighed.

And suddenly Gabe made sense to me. He'd always seemed respectful and kind, reserved, but naive and timid and incredibly, unexplainably shy. "What would you like to do tonight, Gabe?" I asked again, very quietly.

He turned so his back was to me. I got up and went to sit on his bed instead of his chair. From there, I could see the side of his face. He didn't turn away, but he didn't look at me. "Will you... I... How can I say this?"

"Do you want me to touch you? Kiss you?" I felt almost protective of him. His innocence made him so endearing. I was incredibly attracted to him, more than I had been before, and I was emboldened. One of us had to be...not nervous.

"Would you?" he said.

I smiled. "Come sit next to me. I can't reach you over there." I held out my hand to him. "Are you sure you don't want a drink? Something to help you relax a little?"

With what seemed to be a great triumph of will, he came to sit next to me on the bed, very close but not touching. "I really don't drink," he said.

"Okay. How about this?" I put a hand on his shoulder, and when he didn't flinch away, I moved behind him and started rubbing his neck and shoulders lightly. He was so tense.

After a few minutes, some of the tension in his shoulders released. I leaned in and kissed him gently on the cheek. He smelled good, like shaving gel and laundry detergent.

He swallowed. "That feels nice," he said. He twisted sideways so he could face me. With a shaking hand, he reached up and cupped my cheek. I smiled at him.

I took his hand from my cheek and guided it up to stroke my hair. When he continued touching me without my assistance, I put my hands behind his head and kissed him lightly on the lips.

"Oh," he said when I pulled away. He licked his lips. I waited, and after another moment, he put his hands on either side of my face and returned my kiss, holding it a bit longer before letting go.

"Okay?" I asked.

He smiled for the first time that evening.

"Do you want to stop?" I asked.

"No," he whispered.

"Mind if I take off my jacket? It's warm in here."

He shook his head and I let my jacket fall to the floor, leaving my shoulders and arms bare. I kicked off my boots, too. Then I kissed him again. He put his arms around me and kissed me back. I opened my lips and poked my tongue out. He backed off, clearly startled.

"Sorry," I said.

"No. No, it's okay. I just...wasn't expecting that." He gave a nervous chuckle.

He pressed his lips against mine tentatively. I put his hands on my hips and put mine behind his neck. I tried the tongue again, and this time he opened his mouth. I opened my mouth wider and he met my tongue with his. He was catching on quickly. His lips were soft, his touch gentle but willing. The kiss went on for a long time. When he finally backed off, he was breathing hard. I was more than a little turned on, myself.

"What now?" he asked.

I took his hands in mine. "Whatever you want," I whispered. "Do you want to keep going?" I was ready to take him all the way, but I wasn't sure how he felt about it.

"I don't know."

My instinct was to back off. I didn't know anyone who'd gone from never-been-kissed to losing-his-virginity in one night. "Maybe we can go for a walk or something another time, and then see where that leads us." I no longer had any illusions that this night would be anything like the dream I'd had!

He looked down. He seemed disappointed and relieved at the same time. He hesitated, started to say something, then kissed me again. I put his hands on my shoulders and he ran them down my back and then back up. His confidence was growing. I stroked his chest, the back of his neck, up and down his back. Suddenly, he stopped and stood up.

"Wait," he said. He was sweating, panting. He looked terrified.

"What is it?" I asked.

"What's going to happen? What are we doing?"

I shook my head. "I don't know. Whatever you want. If you want to stop, we can stop."

"I don't know what I want," he said. He sank back down onto the bed beside me.

"Okay. That's fair," I said. "Are you uncomfortable?"

He nodded.

I wondered just how little he knew about sex. I mean, surely he'd watched movies and TV shows where they talk about it, or even do it, right? He had to have some idea. He had to have masturbated before. Don't all teenage boys do that? I had the incredulous thought that maybe he had never actually orgasmed, and that's why he was so out of sorts. "Gabe, um, were you thinking we might have sex tonight?"

He put his hands over his face and nodded.

"There's no pressure, you know."

"I know," he said. Then words started pouring out of him. "I really like you. I've liked you for so long, ever since we lived on the same floor freshman year. I used to watch you bring that guy into your room and wish it was me. And when he dumped you, I wanted to be the one to comfort you, and I was so angry at him for making you sad, but so happy that you were available. But I couldn't find the courage to talk to you or ask you out or even sit next to you in the dining hall. And I don't want to be that guy anymore, the one who watches from a distance and pines away and misses my chance. So I asked Anya to set up this party and keep Jonah away and - well, now here we are and I'm so mixed up and overwhelmed because you're here. You're really here in my room and I just want to touch you and hold you and be with you. And I'm afraid of what comes next because I don't want to disappoint you."

The barrage of words ended. I didn't know what to say. I'd had no idea he felt that strongly. "I like you, too," I said. "And I don't want you to feel pressured to do anything just because you think I expect it." I held out my hand and he took it. I stood up and pulled him to his feet. I wrapped my arms around him and leaned my head against his shoulder. He hugged me tightly and kissed the top of my head.

When he loosened his grip, I lifted my head to look up at him. He met my eyes, then hesitantly bent his face toward me and kissed me. I held him in a slow, sweet kiss and let the tension build, then ran my fingers through his hair and down his back. When I reached his waist, I untucked his shirt and slipped my hands up underneath it. He gasped, but didn't pull away. I caressed his back and then around and up his chest. He froze. I waited, looking up at him. I rested my hands on his stomach under his shirt.

"What is it?" I asked. My voice was husky.

"I want this more than anything I've wanted in my life," he said.

I smiled. "Kiss my neck," I said. "Right here." I pointed to a spot just under my ear.

He put his hands on my shoulders and did so. A shiver ran through me at the light touch. "Does that feel good?" he asked.

"Yes," I said. I returned the gesture, then kissed down the side of his neck to his collar. As I did so, I unbuttoned the first two buttons of his shirt and continued the line of kisses to his collarbone.

"Should I take my shirt off?" he asked.

"If you want."

He pulled his shirt up over his head, then kissed that spot on my neck again. He copied my string of kisses down to my collarbone. His touch was so gentle, but he was less hesitant. He touched my shoulders and trailed his fingers down my arms. I guided his hands to my waist and up under my shirt. Slowly, ever so slowly, his hands inched upward. He stopped when he brushed against my bra.

"It's okay," I said. "Go ahead."

"Are you sure?"

I laughed. "If we're going to have sex, you're going to touch a whole lot more than that," I said.

His cheeks reddened.

I reached around behind me and unhooked my bra, then shed my shirt and bra quickly. "There," I said. "Now we're even."

He stared at me. It was like it hadn't occurred to him that we would have to get naked to do this. His eyes flitted to my exposed breasts, then back to my face, then back to my breasts.

"Oh my gosh," he said.

"I'll take that as a compliment." I smiled, trying to lighten the mood.

He laughed. It was a nervous laugh, but it was a laugh. "Can I...touch them?" He reached out toward me. I took his hands and put one on each breast. I moved in close to kiss him on the mouth again.

After a moment, I backed away. "If you think something might feel nice, go ahead and try it," I said. "I'll let you know if I don't like it. And you let me know if you don't like something I do."

He nodded but didn't move. "Do we need, you know, a condom?" he asked, concern heavy in his voice. I assumed he didn't have one.

My thoughts raced. He's a virgin. He must be clean. He's never even seen boobs before. I was on birth control and had been tested. It was okay, wasn't it? It had been drilled into me that you don't fuck someone new without a condom until you're both sure it's safe, but...who could be safer than Gabe? I couldn't bear to break the mood and go all the way to my room to get a condom. "I think we're okay without one," I said. "If you're okay with it. I'm on birth control."

He nodded. "I trust you," he said. He took a step toward me and stroked the sides of my breasts with his fingertips, then leaned down to kiss my nipples. "They're soft," he breathed.

I entwined my fingers in his hair and held his mouth to my nipple. After a confused moment, he opened his mouth and sucked experimentally. I moaned at the sensation. With that encouragement, he sucked harder, then switched to the other side. It was almost like he was trying out things he'd read about or seen on TV but hadn't believed people actually did to each other. I hoped he'd read the right kind of books.

He was good at this. With each suck, he flicked his tongue across my nipple. I wanted more, and he seemed willing. Quickly, I unbuckled his belt. He didn't seem to notice. All his attention was on my breasts, touching one and sucking on the other, then switching. I unbuttoned his pants and unzipped his fly. He grunted but didn't protest. I slipped a hand down the front of his boxers and touched his cock.

His breath exploded out of him. "Ooohhh," he moaned. Clearly no one had ever done that to him before! I grinned and pushed his pants and underwear down. His cock was hard. He stood up straight and let his pants fall to the floor.