Dating Lessons

I had been divorced for two years when my friend Michael took me on a date. It wasn't supposed to end up the way it did, though...

Let me explain. My ex-husband and I started dating when we were in our teens, and were married for five years, so there I was: a twenty-seven year old who'd never dated as an adult. Michael pointed this out while he helped me repaint my kitchen.

"You're a babe in the woods, Jeanette," he said calmly, from up on the ladder. There was a tray of paint on the shelf. Michael hadn't let me paint from the ladder, not because I'd hurt myself, but because I would have knocked the tray off immediately, all over the hardwood floors we hadn't taped off.

"What is there to know?" I said. "They pay for everything and maybe I let them kiss me on the front porch."

Michael laughed. He looked like me, with dark hair and electric blue eyes, and pale skin. He was a carpenter, though, strong and methodical, and I was the art teacher. As kids, we'd been neighbors, and because he was slightly older than me, he was my protector. He'd been like a brother to me. My ex had been one of Michael's good friends, but the night after I called Michael in tears for the first time over my husband's infidelities— well, Michael showed up at my parents' doorstep with a black eye and gave me a big hug. You should have seen the other guy, he said, and I knew it wasn't right, but it felt good to know he was there for me.

"How about this. Let me take you on a practice date. I'll pick you up at seven on Friday night. We act like we've just met."

Worst case scenario? I'd get to hang out with my best friend. I shrugged. "Ok. Why not."

***

Friday came, and by seven, I was surprisingly nervous. First off, I couldn't figure out what I was going to wear. There were two dresses I had picked out. My favorite was a flirty pink number that set off my tan skin, but the fabric was too thin to wear a bra and if I got even the slightest chill, my nipples were visible. The other was navy with a short hem that showed off my long legs. I got into the latter.

Don't laugh, but I'd taken a shower and for the first time since the divorce, I shaved my pussy. It took a while. That's how my ex-husband had liked it, rubbing his thumb over my bare mons. That's how I liked it, too. Visually it was nice, and shaving made it more sensitive. Sure, this was only a practice date, but I justified it because it made me feel like I was going on an actual date. It's important to be in the right mindset, I told myself.

I answered the door in my jacket, purse on my arm.

Michael frowned. "What are you wearing?"

"A dress," I said.

"Let's see."

After he made me unbutton my coat, he gave a nod. "What else do you have?"

"What do you mean?" I said. "I chose this."

After some discussion, he made me go change into the pink thing. The temperature had dropped from the open door, and my nipples poked out. I pointed out that this dress was a little...revealing. Michael waved away my objections without seeming to notice.

"This time answer the door with no coat. You don't want to look like you were waiting. That'll make you seem too eager, make it look like he has the advantage."

The doorbell rang. I opened it. "Hi. I'm Jeanette."

"Michael," he said, and we shook hands. I let him in, and offered him a drink. Walking to the bar, I got out the rocks glass for his customary whiskey, but he surprised me by asking for a martini. My hand hovered over the gin bottle. Walking around the house with his hands in his pockets, he looked at my art as if he'd never seen it before.

"Olive? Or onion?" I asked as he examined the still life hanging above the fireplace.

"Olive," he said, and lowered his voice. "And make it dirty."

As I sloshed a bit of juice from the jar of olives into the shaker, I blushed. How many secrets had we shared over the years? Yet this was the time I had heard that secretive voice. This is how he sounds to other women, I thought. He's dead sexy.

"I'm going to finish getting ready," I said, handing him the glass, and scampered to the bathroom where I patted down my damp pussy with a tissue. My face was burning. Once I'd composed myself, I went back into the living room where Michael was swirling his drink around his glass with a thoughtful expression. He smiled.

"You have to keep your cool," he said.

I picked up my jacket and shot a cold look. "Ready?"

On the drive to the restaurant, he asked me to tell him about myself. I told him I was twenty-eight, an artist. I liked to travel, and had been to Australia in the last year. My favorite food was Thai. I had an ex-husband who was a lying sack of—

Michael stopped me, gently. That wasn't fun to hear about on a first date. The spot he had picked was casual and cozy, with a string of small booths alongside a beautiful bar. I suggested we sit up there, rather than get a table. Michael nodded, and took my jacket to hang beside his on a coat tree. Sitting side by side is more intimate than face to face, and we could still see each other in the mirror behind the bottles of liquor. Michael had another martini, and I got a glass of red wine.

"It'll make your teeth pink," he said, reading the menu.

"If my date doesn't like pink teeth, he can take a hike."

Michael smiled, and we shared a starter plate. The bartender brought a small board with olives, cheese, pate, and some crackers. I didn't mention my ex again. I asked him about himself. I'd never heard Michael describe himself before. I was surprised at how humble he made himself sound, how down to earth. His amazing carpentry turned into mere handyman work, his volunteer job into a casual two hours every week.

"You're selling himself short," I said. "No wonder you haven't had a girlfriend in years. You should tell your dates the truth. You love cooking, and karaoke, and hiking, and helping your friends. You're tall, and fit...and sexy."

"Maybe you think so," he said fed me an olive. His fingertips brushed my lips lightly, and I felt that rush again. Stop. Our food came then, to my relief. We ate and then he suggested we walk through town, get a nightcap.

"I bet you guys have great sex!" the street kid hollered at us, and Michael laughed and handed him a dollar. I blushed, felt a tingle. There was a bar down the street with a live band.

"Let's go in here," I said, pulling him towards the door. Inside was loud, with dim lights and a good band with a small dance floor in front of them. A few people were blues dancing very closely. My ex hated dancing, but I knew Michael couldn't resist, and in a second, he had me against him. Not as tight as the other people on the floor.

"Tighter," I said, tilting my head back so my long, dark hair shimmied down my back in a silky river. He buried his hand in it, tugging it, keeping my chin tilted. "Tighter. Come on, Michael. Do it right."

He turned his head to the side and smiled, and obediently held me to his warm, strong chest. It only took a moment for us to find the rhythm. He still held me gingerly, and I soon figured out why. Michael had an erection. At one point, it brushed my thigh, and it was his turn to blush. He kept laughing, and wouldn't tell me why.

"You're a good dancer," I said, pressing in to him. "So how am I doing on this dating thing?"

"Really well," he said. "Actually, I think you may be better at it than me."

"Would I get a goodnight kiss?"

He tipped my head back again and surprised me by kissing me then, on the mouth. Not a surprise, really. There was no shock, just an electric feeling all over my body. Briefly our tongues met, and then I buried my face in his neck. We kept dancing. He slid his hand to my lower back and caressed me through my dress.

"Do you want to get out of here?" I asked.

Five minutes later, we were in the car, heading back to my place, holding hands. We didn't speak. As the road whizzed by and the ten mile marker came up, I floated in the lovely thrill of erotic feeling. My nipples were hot, jutting against the dress shamelessly, and my pussy was damp. I could smell it. Michael probably could too. I looked over at him once and he smiled, and squeezed my hand. We didn't ask if we were really doing this. We were.

He waited until I had shut and locked the door behind us. As I turned to ask if he wanted a drink, he put his mouth on mine, and gave me a long, slow kiss that deepened and sweetened. One hand was on my waist, and the other slid down my back to my ass. He gave it a squeeze. Both of us were panting. The house was dim and the air was warm, and I pressed into his hardness with my thighs, rubbing gently at the rigid flesh behind the zipper of his slacks.

"You make me so wet," I whispered, and he nuzzled my ear with his lips, tracing the lobe, filling my body with his breath. I grabbed the edge of my dress and pulled it over my head in one swift motion, exposing my red lace thong and naked breasts. The nipples tipped upwards towards Michael, begging to be touched. He took the right one in his hand and lowered his mouth to the other, using his lips to pull it between his teeth. Jolts of heat ran through my body, a direct line of nerves from breasts to clitoris. He tongued the now-sensitive nubs roughly, and I squeezed my thighs together.

Michael backed me slowly to the antique chaise lounge, and reclined me on it comfortably, putting my head on the pillow. He kicked off his shoes and slowly unbuttoned his shirt to expose his strong chest, lightly furred with dark hair. He stood, looking down at me, unbuttoning and unzipping his trousers, and stepping out of them. His thighs were strong and thick from biking, and I got a moment to admire his body, at the thing straining grotesquely at the front of his burgundy boxer briefs.

The chaise lounge was made for fucking. Michael straddled me easily with both feet on the ground, using the slightly raised back as he again played with my tits, suckling them and kissing them, covering my chest and neck with his mouth. We made out deeply, and I slid my hand down his stomach, stopping just before his erection. He arched his back and groaned.

"Not yet," he whispered in my ear. He kissed and licked and ran his teeth to my navel. Hooking his thumbs in the waistband of my thong, he dragged it down to my knees and I pulled my leg up and out of them and kicked them off. I lay back, vulnerable, exposed. He gazed at my pussy reverently. "Holy shit."

He lowered his chin. Peeping out from the rosy pink folds of my vagina was my hard little clit. Sticking out his tongue, Michael touched it, his stubble brushing the lips of my pussy. It was almost agony, I almost came right there. My hips bucked. Moisture stuck the tops of my thighs together.

The next lick was longer, running up the labia and then in slow circles around the clit. It was exploratory, it was like he was revealing my body to me. I pressed my head back on the pillow, and he began to work, licking and licking and getting every bit of me. My legs parted on their own, and he pulled one hand from my tits, and used it to trace the line of my sex with a rough fingertip.

"Mmmmm," he sighed into my snatch. His finger probed south of where his mouth was occupied, finding the soft opening and pushing in.

"Oh yes!" I said, panting, as one thick finger wiggled in my fuck tunnel. His mouth latched on to my clit, sucking and licking hard and fast. The finger slid out. The finger slid in. Out. In. Out. In. The rhythm built up to a steady finger fucking. I was getting close. I knew he was just warming me up for his cock, and the anticipation was slowly driving me to the edge. "Are you going to make me come, Michael? Is that what you're trying to do? Do you want me to come all over your fingers?"

He laughed, quietly, and pulled back. "No."

Covering my pussy with his hand, he stood up.

"What the fuck?" I said. "I was so close."

As a response, he stepped out of his boxer briefs, and stood there in the warm glow of my living room, naked. Oh, he was gorgeous. Tall, the fur of his chest growing thinner, forming into a line that circled around his flat stomach and hurried downwards. He had trimmed his pubic hair to short curls, and emerging from that was his cock. It was long, thick, red, and bent slightly to his left. I imagined him jerking it, thinking of me. Two big balls hung like soft fruit. He stepped towards me, cock bobbing with every step.

The head wept a single drop of pre-come, beading at the top like a bit of sugar syrup. He offered it to me, and I opened my mouth. He touched it to my top lip, and I swept the tip with my tongue, causing him to shudder in ecstasy. Reaching up, I took the shaft in my hand, squeezing it lightly. The thick head was swollen and red and I wanted to bury it deep in my body but for now, I pulled him to my mouth and suckled his prick.

Artfully he swept his leg over my head, straddling my body so we could sixty-nine. He buried his mouth in my snatch, licking me madly while I guided his hard length to my mouth. I jerked him off slowly as he again brought me to the edge with his mouth. We frantically moved together, and again I was going to come in his mouth when he pulled away and we gasped for breath, his scrotum tight against the crack of his ass.

"I want to fuck you so bad," he said, and got between my legs. Without waiting for me to say anything, he brought the thick red head to my sodden pussy lips. He slowly slid in, stretching me out with every inch he crammed in my wet hole. It was a long, slow, screw. Helmet and veins scraped the inside of my pussy thrillingly.

"Fuck me," I said, putting my right leg over the back of the chaise lounge, offering myself to him. He pulled out so just the tip of his machine was in my vulva, and teased it, popping in and out of the ring before pushing all the way in so he was balls deep and we both groaned with pleasure.

"You have such a tight little pussy," he said, wetting his thumb with my juices and using it to massage my clit. "Your husband always told me what a tight pussy you had, what a good fuck you were. He used to think he was making me mad, telling me how dirty you were, what a good cocksucker you were. 'Jeanette sucks my cock like a cheap whore,' he'd say. 'I bent her over and fucked her on the couch the other day, just cracked that pussy open with my big cock and blew my load all over her face.' He would tell me that, trying to make me mad."

"Did it make you mad?" I said, as he rammed in and out of me. I was going to come, and there was no way I was stopping this time. He was pushing me over the edge.

"It made me jealous," Michael said, a manic gleam in his eyes. His sinewy body worked and stretched my hole. "And it made me so horny. He'd tell me that at a bar and I'd go into the bathroom and jerk off. I'd shoot my cum all over the walls of the stall in about thirty seconds, thinking of him fucking you and leaving his cum inside of your tight pussy. Come for me, Jeanette. Come on my big cock."

I whimpered, and I put my hand where he was and rubbed in fast, light circles. One thing my ex hadn't told Michael, apparently, was that I was a squirter. A second later, I began to gush. His penis started sloshing, and his eyes widened in amazement as I began to shake and moan, the biggest orgasm I'd ever had ripping through my body.

"Oh, oh, oh," he said, grabbing my hips and slamming hard into me, his mouth opening as he came too, unable to stop what had triggered. He came inside of me, matching me spurt for creamy spurt, and ground deep into my pussy, cum seeping out at the thin joint between our bodies. He collapsed on top of me, our hearts beating irregularly as our bodies settled down. After softening, his cock tumbled out of me, and I could hear our moisture pattering on the upholstery of the couch. I didn't care.

"So is this how it goes?" I whispered. "Was tonight a success?"

He laughed, and kissed my right breast. "Good ones mean you get asked out again."

"Yeah?" I waited.

"So...what are you doing tomorrow night?"

"You," I whispered.

"Sounds like a date," he said.