First Time for Old Friends

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I had known Casey since freshman year of high school. Damn, that was ten years ago now. We had always been the best of friends, from that day in English class when we both got in trouble for reading while the teacher was droning on. We were the nerdy rebels. Everything about her was special, to me at least.

She had been there for me for so many things. My first girlfriend, first breakup, my parent’s divorce, and all the good times too. I’d been there for her after the guys she slept with didn’t call back, the day she got into college, the day she managed to talk to the guy she’d been crushing on, and, of course, when he had broken her heart, four years later, which is why we were sitting in my basement apartment drinking. We’d had a couple of beers, a few glasses of wine, and several shots of tequila. Now, we were playing the Never Have I Ever Game with Jack and Coke. The instructions are simple, say something you haven’t done, and if the other person has done that thing, they have to drink.

“Never have I ever watched more than one Disney movie in a row.” I said.

“Dick!” She retorted, drinking from her mug of Jack and Coke. She grimaced. I had made them really strong.

“Uh, never have I ever took apart a car.”

I drank. We too much about each other to play this.

“Never have I ever fucked a professor.” I smiled, wickedly.

She didn’t drink.

“You bastard, I didn’t fuck him, we just made-out. AND HE WAS A TA!”

I laughed, she giggled her drunk giggle, but then stopped. She bit her lip nervously, as if deciding on something.

“Never have I ever… licked an asshole.” She slurred her words ever so slightly. I couldn’t tell if it was from the drinking, or talking too fast in excitement, but I nearly dropped my drink. We had had made the decision long ago to say if we slept with someone, but not give intimate details. I looked at her blue eyes, which were staring at me with an intense curiosity.

I drank.

Her mouth opened a bit, in awe, I thought, and made it painfully obvious that she didn’t have to drink. It was my turn, and I wasn’t going to breach the subject again.

“Never have I ever cut a Barbie’s hair.”

She frowned and drank. I wanted to ask what was up, but I just couldn’t. I didn’t know where she was going with this at all.

“Never have I ever had anal sex.”

I coughed. “What?”

“Never have I ever had anal sex!” She repeated.

I drank.

“No shit! With who?”

“It’s not your turn.”

“Please? Who?”

“For fucks sake, Tammy and Lisa.”

“That’s half the people you’ve slept with!” She said, spilling some of her drink.

I sipped mine. Usually she could hold her liquor but she had to be drunk as hell to be talking about this.

“Gregg?” she asked, softly

“What?” I said, my eyes narrowing at her her.

“Would…. uh….” She stammered. “Would you take my anal virginity? I mean, I, uh…”

I had to run to the bathroom because I had just snorted my drink, and whiskey didn’t feel good in my sinuses. I cleaned up, walked out of the bathroom, and saw her sitting in the same place, her drink now on the floor. She had a determined look on her face.

I sat down in my favorite chair and she stood up and began to walk toward me. She was beautiful, and always had been. Her hair was a soft brunette that didn’t make a big deal out of itself.

“Look, I know you’re drunk so let’s just ignore that last bit and get some sleep. You can have my bed, I’ll sleep on the couch, like normal.” I was just about to say something else when she did something I was expecting; she straddled my lap. Her face was inches away from mine, staring deeply into my eyes.

“I want you to do it,” she whispered. “I actually talked to Lisa about it before you broke up. She said you’re amazing at it and I want my first uh, anal, to be amazing, please?”

“Casey, god dammit, get off me, you’re drunk and still sad about that motherfucker…”

She ignored me talking about Chad, her now ex. He apparently had decided shortly after their fourth anniversary that he was only with Casey out of convenience and that was that. She had spent the last week at my place, going to get her things pendik escort slowly from their apartment, while Chad was at work.

“No. I need this, I need this for me.” She reached to the bottom of her shirt, and before I could do anything, it was on the floor. I looked straight to her chest. Her pale white breasts were covered by a black lace bra. I won’t lie, I had noticed a long time ago how perfect those breasts are. Seeing them this close to being bare, it was almost too much to handle. I could feel myself getting hard, even though I didn’t want to.

She felt it too. She smirked. “I think you want to do it…” She said seductively. She got off of my lap and dropped to her knees on the floor.

“Casey…” I whispered. I should have stopped her. I should have stood up and started to walk away but then, she looked up at me and unzipped my jeans. In a few swift motions, her hand had released my cock, and it was now sticking out from my boxers. I was rock hard. It had been way too long.

“Casey,” I whispered again, but it was too late. She took my cock into her mouth, as deep as she could go. All I could see was a mass of brown hair as it slowly bobbed up and down, her sucking me off. I moaned, deeply. She started to lick up my shaft, to my head. I couldn’t do it like this, it had to be right. I grabbed her bare shoulders and pulled her away from my cock.

“Dammit Gregg, please!” I paused.

“We can’t, you’re not even stretched, we’d need to work on getting your ass used to taking things, like a butt plug…”

I paused when I saw her biting her lip. Her eyes darted to the bag she had brought from her apartment.

“I, uh, have been.”

I stared at her.

“I thought Chad would like it, maybe want to try something new. I’ve been stretching and getting used to it for months.”

My cock pulsated.

“Okay.” I whispered. “But, if we’re going to do this, we’re going to do it right.” She looked puzzled as I stood up, helping her to get feet. I kicked my jeans off, put my cock back into my boxers, and grabbed her hand.

I led her to the bed, and laid her down on it.

“What do you mean the right way?” She asked.

“When I am with someone, I want them to feel what I want them to feel.”

“What does that mean?”

“You’re beautiful. I’m going to make you feel beautiful.”

I slowly crawled over her body until our eyes were staring into each others. I knew she didn’t expect that, I knew she didn’t feel it, but god dammit, if this was happening, it would be the best thing she ever felt.

I lowered myself slightly, and pressed my lips to hers. They were so damned soft. I slowly ran my tongue across her bottom lip. Her mouth opened slightly and I slid my tongue in. We kissed for what felt like hours. Slowly, I moved my hand under her and felt for her bra clasp. It was undone in a second. She lifted up slowly and I tore it off of her, throwing it to the floor. I didn’t want to stop kissing her but I wanted to see her bare breasts below me. I pulled away from our kiss.

“You’re better than I remember,” she said, giggling.

We had practiced French kissing on each other during sophomore year of high-school. It had never gone past that. I smirked. I wanted to tell her how sweet she tasted, and how it was the same all those years ago. Then, I looked down. I had almost forgotten she was nude from the chest up. Her beautiful, C-cup round breasts were there for my eyes to drink in. Her nipples were hard, and a soft pink color. They were right in the center of each breast, begging me. I inwardly groaned, my cock throbbing between my legs. I straightened on my knees and threw my shirt onto the floor.

As I leaned back down, my chest could feel her hard nipples rake across my skin. I kissed her nose, then her chin, and slowly left a trail of kisses down her jaw line. When I reached her neck, I kissed and sucked down it softly, her breath coming in tiny gasps.

As I kissed across her collarbone, I found myself growing excited. Her ex had confided in me that she had the most sensitive nipples he’d ever touched. He had asked me what to do. In all honesty? I told him to just suck them harder. I couldn’t stand the idea of him making her feel escort pendik good. I knew what I was doing. When I got to her breasts, I kissed down the left one softly, until I got to her perfect left nipple. I darted my tongue to it and flicked it, softly. She whined. I smiled and slowly began to run circles around its point, making her moan as I did. I reached my hand up and slowly began playing with the opposite pink nub. She was squirming. Then, I moved my mouth to it, slowly beginning to suck on her as I did. She whimpered and writhed in pleasure. As I sucked, I wondered inwardly if…

Well, I had to try it I very slowly stopped sucking, but kept my mouth on her nipple. She ran her fingers through my hair, silently begging me not to stop. I extended my teeth and gently placed pressure on her nipple. She yelped. I pulled away, scared I had hurt her, but knew it wasn’t the case when I saw her head was thrown back, and she was biting her lip. A pleasure yelp. I smiled. After mirroring my actions to the other breast, I gently pushed myself up. My hands found the button to her jeans and undid them. She wiggled out of them as fast as she could. When they hit the floor, I looked back to her body to see black lace underwear that matched her bra. All-in-all, it was amazing. Her body was perfect, an hourglass shape that I had to run my hands along. She looked at me apprehensively and I knew she must be feeling that nervous feeling we all know when we’re seen naked by someone new. I stared into her eyes.

“You are more beautiful than I could ever have imagined,” I paused. “And I have tried.”

She blushed and tried to sit up, her hand coming up towards my cock. I pushed her back down.

“This is about you. My cock is hard enough as is.”

She giggled, but I was already moving her underwear down her legs. When her scent hit me, I thought I would cum immediately. Thank God I was tipsy, it made it harder for me to orgasm. I got down on my stomach and she spread her legs, as I looked at her cunt for the first time.

Her hair was trimmed down, but not shaved, which was how I preferred it. Her lips were pink and covered by a perfect, symmetrical slit. The wider she spread her legs, the more perfect it looked. I went to work immediately. The first thing I noticed as my tongue probed her folds was that she was absolutely soaking wet. The second was that she tasted like a strawberry, sweet, with a hint of bitter. It was fucking amazing. I kept teasing her, licking up and down her, flicking her clit just barely, and when I couldn’t take it anymore I just started licking and tasting her as much as I could. She was writhing, draping her legs over my shoulders, and grabbing at her breasts. Then, it happened. She moaned out my name.

I wanted to make her orgasm right then. That wasn’t what she wanted, though. I had imagined her saying my name like that for years now. I pulled away from her and she looked at me, panicked. She was wondering if she had done something wrong. I smiled and grabbed her hips, flipping her onto her stomach. Her gorgeous ass laid in front of me. She looked over her shoulder at me, and raised up onto her hands and knees.

As her head moved back, she asked, “Do-do-do we need lube?” I smiled, and didn’t say anything. My cock was still in my boxers. I leaned down behind her and spread her ass cheeks. I felt her tense nervously as I leaned in and softly kissed her asshole.

“OH.” She said loudly.

I chuckled.

My tongue came in contact with her and I started to lick. She moaned loudly at every flick of my tongue, every time I prodded her tiny asshole. Her cunt was so wet it was dripping down and surrounding her asshole. When I was done licking her, I pulled away and she pushed her ass back, wanting more. I knew she was ready. I stood up, making eye contact with her as I slid off my boxers. She got a good look at my cock. It wasn’t small, but it wasn’t giant. It was average, and it would make this a little easier.

In a fluid motion, I hopped off the bed and grabbed for my bedside drawer. I grabbed a condom from its box and began to open it to place it on myself.

“Gregg?” she whispered.

“Mmm?” I said, fiddling with the irritating device.

“Could… pendik escort bayan could we not use a condom?” she said.

I paused.

“I mean, I’ve been tested, if you’re worried…” she trailed off.

“No, it’s fine. If that’s what you want.”

I was almost certain my cock would just surrender to her and leave me alone. This woman was amazing. I threw the condom to the floor and walked to the bed. I grabbed a bit of lube, though, and put some on, I didn’t want this to hurt. I positioned myself behind her, she raised onto her knees again and let me kiss her. Then, she bent back down in front of me, spreading her legs, and showing me her wet asshole.

I positioned the head of my cock at her tiny, puckered entrance. I placed my hands on her hips and brought them towards me, slowly caressing her as I did. My hands moved towards her ass, grabbing my cock and very slowly moving it forward. As I started to enter her, bit by tiny bit, she moaned out each time.

Before I knew it, the head of my cock was in her asshole. I looked down at the sight before me and made myself not thrust the rest in. I had to be patient, slow, I wanted this to feel so good. I moved forward more, slowly, even more slow, and she whined.

“Gregg… faster…”

I hesitated.

“Please!” she exclaimed.

I couldn’t think after that, and I pushed the rest of myself in. Her entire ass had managed to swallow me whole. I could feel her pulse and mine as they began to beat in time. I moved out of her ass slowly, and back in, slowly, and back in.

“Fuck, Gregg. Fuck that feels…. good. So fucking good.” Casey said this between very ragged breaths.

I’ll admit, I gasped a little bit too as my pace sped up ever so slightly. Of course, my pleasure didn’t matter – though it was amazing how good this did feel. As I thrust deep into her, filling her again, I reached my hand around the front of her hips to her cunt. I found her clit quickly and began to massage it as I pulled out. I could feel her ass pulsing, begging for me not to leave her, but now that I knew there wasn’t really a risk for pain, we could have some fun. I put my cock at her asshole, which was now wider, and much more welcoming to my cock.

I began to rub her clit in tiny circles, fast, fast, slow. Then, I began thrusting in the same rhythm. Fast. Fast. Slow. Fast, fast, slow. She moaned at each thrust and before I knew it, the pattern was gone completely and we were both giving into what we wanted. I pulled out, and I thrust back in, gently, but with a vigor that I knew felt good for her. All the while my fingers prodded her clit. My hand was soaked in her juices.

I felt her ass clench around my cock my quicker than normal and I heard her whimper out:

“Gregg, I’m… I’m….”

I was going to come, too. I picked up my pace just a bit, and I felt her orgasm shoot through her body, and at the same time, my balls tightened, I thrust, and I came. She was calling out my name, over and over, her body writing and shuddering as she did. I grunter and I pumped myself into her as she began to relax, my fingers giving her very soft and easy strokes on her clit. We stayed with her knelt in front of me, and me kneeling behind her for a few moments as we caught our breath. Then, very slowly, I began to pull out of her. As I did, droplets of my cum spilled out of her asshole. It was sexier than I could have ever imagined.

I laid beside her and pulled her close to me, her whimpering softly as orgasm still struck through her body. Her back pressed against my chest and I ran my fingers over the curve in her hip, up her side, and then lingering at her shoulder. I kissed the top of it carefully and waited for a moment before I softly whispered:

“Casey, I love you.”

“I love you too.” she said back, turning her head to look into my eyes.

“No,” I paused. “I, well, I am in love with you. I think I have been for a long time.”

She bit her lip softly, her front tooth making her bottom lip turn slightly off-color. My heart hurt for a moment, panicking at what would be coming next.

“That’s what I meant, I love you, Gregg. I always have.”

My heart jumped from my chest and I turned her towards me, kissing her as deeply as I could. When we pulled away, she giggled, still a little drunk, but sobering up, and I smiled, wondering what tomorrow would be like if this was only our first night together.

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