Casual Encounters Newbies

Note: The following was written before Craigslist dropped its Casual Encounters section—a sad loss!!!

*

"M-mmm." My girlfriend Nancy let out a little appreciative sound close to my ear.

We were sitting on the couch in Nancy's apartment, watching a porn video on the TV screen we'd wired to her laptop. It was a warm June evening and we were both in just shorts and t-shirts, our feet bare. In front of us on the TV screen a pretty blonde, naked but for the loosened pink bra pushed down around her waist, had taken her lover's cock deep into her mouth, letting a steam of saliva run from her lower lip.

"M-mmm," Nancy whispered again as the blonde let the big cock slip out of her mouth for a moment before starting to lick back and forth across the circumcised knob.

Nancy loved porn, something I'd discovered on a visit to the apartment several weeks earlier. She'd hurried to the door to let me in but failed to turn off her laptop. I'd heard a moaning sound and flipped the lid open to see a large black cock thrusting in and out of a very wet pink pussy. Nancy had reddened in embarrassment before confessing this was something she often enjoyed on the evenings when she was home alone.

We were graduate students at a western Oregon university and had been sleeping together for almost a year. Nancy was a wickedly cute little Asian girl, with a mass of shiny black hair and a body kept slim by running every day. I had boringly average mid-brown hair, trimmed short, but I was also in good shape after four years of college soccer as an undergraduate.

In front of us, the pretty blonde had been pushed onto her back with her legs wide apart and her dark-haired partner was starting to eat her out. I turned the sound down a little; the blonde's moans were getting loud.

Next to me, Nancy had undone several buttons and slid her hand down the front of her shorts. I undid my belt and unzipped my own shorts. Nancy turned to give me a mischievous grin before helping pull out my stiffening cock. She gave it a quick lick before turning back to the screen where the man had rolled onto his back and the blonde was climbing on top of him.

The camera slowly zoomed in to show the man's cock pushing at the girl's pussy entrance. The blonde let out a little appreciative cry as the shaft disappeared inside her cunt.

"That's very nice," Nancy commented. "I can almost feel that cock. Nicely shaved, too."

Still in cowgirl mode, the blonde began a slow up and down ride on her partner. With each thrust, she lifted herself just enough for the man's cockhead to become visible before her pussy lips swallowed it again.

Nancy stopped playing with herself long enough to slide her shorts and bikini panties down her legs and onto the floor. I followed suit with my own shorts and underpants, allowing my cock to spring completely free before Nancy's mouth moved around it, her tongue sliding up and down in time with the blonde girl's ride.

"Enough," Nancy announced after a couple of minutes, turning back to the screen where the blonde was switching to reverse cowgirl position. "I don't want to miss all the action."

I slipped two fingers into her pussy, causing her to wriggle a little. "Doggie?"

"Mm-hmm, best for watching." Nancy slipped off her t-shirt. She wasn't wearing a bra and with her slim athletic figure didn't need one, but I always liked to see the thick nipples and dark areolas against her olive skin. I gave both nipples a long suck before she climbed onto the couch to give me a nice view of her tightly-muscled rear and wide-open wet pussy.

Removing my fingers, I positioned my prick at her entrance, wiggling it a little to touch her labia. She was still rubbing one hand across her clit, and was now very wet.

"Push it in, Pete," she muttered over her shoulder. "I'm ready for cock, even yours."

"Okay." I pushed my prick slowly into her, feeling her cunt walls yielding. My penis wasn't among the world's longest, but it was unusually thick, and she'd found it hard to take when we were first lovers.

"Ooh, ooh, ouch," Nancy moaned quietly as I touched bottom.

"Okay?" I asked.

"Just about, move it a little, that should help. Or maybe I'll get even wetter watching the video."

I could see what she meant. On the TV screen, the blonde was now draped over the end of the bed, her ass high in the air, with the dark-haired man ramming his tool hard into her. After each thrust, he pulled slowly out, bringing a little creamy juice, until just the tip of the head was touching the girl's pussy lips, then plunged back into her. With each thrust the blonde gave a little scream.

The camera switched from the man's cock to the girl's face for a moment. Pain, pleasure, pain, pleasure, appeared in rapid succession as the man speeded up his movements.

Following their rhythm, I was moving faster and harder, too. Nancy was moaning loudly with each thrust from my cock. I was rigid from what we were watching on the screen and the pleasure of pounding her from behind. Sensing her excitement was building, I licked one finger and inserted it in her tight brown butthole. I pushed it in farther, wiggling it around, watching her ass cheeks flexing with each of my movements. I speeded up my fucking and pushed my finger in a little deeper, causing her ass to thrash from side to side as she alternated between trying to escape and trying to embrace my thrusts.

I pushed the finger in as far as it would go.

"Aaagh!" She screamed, causing me to feel my own climax coming. I pulled out for a moment, causing Nancy to emit a long panting sigh, then reinserted my cock. Hard!

"Aaaagh!" She gave another scream, and then I was pounding into her cunt, getting closer and closer, then cumming with a gush that left me breathless.

On the TV screen the video was still running. The dark-haired man was ramming the blonde girl's cunt as if his life depended on it. Suddenly he pulled out and flipped the girl around. The camera zoomed in as his cock twitched violently, then sprayed a thick stream of creamy jism across the girl's breasts. As the blonde pushed out her pink tongue to lick up a spot of cream that had landed on her chin, the picture slowly faded.

My own cock was finally softening as Nancy turned from the screen to smile at me. "I'd love to see that," she said.

"You just did," I told her.

"No, idiot, I meant for real, right in front of us. Wouldn't that be great?"

"Um-hum." It sounded like a fantasy. But an attractive one.

"Right in front of us," Nancy repeated. "A sexy couple, fucking their brains out. Close enough to touch."

Even though I'd cum just a minute before, I felt my cock give a little jump.

Nancy wriggled around on the couch to give my damp shaft a lick. "Seems as if this likes the idea!"

"But who could we get to do it?" I was definitely starting to get hard again.

Nancy gave my cock a little slap. "No more for now, buddy, but I'll get a couple of beers and we can talk about it."

We drank several beers over the next hour, running through the names of couples we knew. There were definitely two or three we'd like to watch having sex, but we couldn't figure out how to propose what we wanted.

"I don't want to screw up a good friendship by shocking people we really like," I said.

"Maybe if we were all drunk or stoned, it would be easier," Nancy suggested.

We'd both been at parties where couples disappeared into a bedroom for a while, but it was hard to imagine planning that ahead of time. We could start to make love ourselves in front of another couple, but suppose they were just embarrassed? And it was some other couple we wanted to watch, not put on a show ourselves.

There didn't seem to be an answer.

"Craigslist," Nancy said suddenly. "They have personal ads. Maybe we can find something there."

I pointed to the laptop. "Let's look."

Nancy grabbed the keyboard, her fingers flashing across the keys. The Craigslist website page for our region of Oregon opened on the TV screen.

"Here we are," Nancy said. "Under 'Personals.' 'Casual Encounters' sounds right?" She clicked on the words. "Hmm, looks like 'MW4MW' is what we want."

There were just seven or eight posts under the MW4MW heading. It was a disappointing lot, we realized as we read them. Most were dated weeks earlier, with only two from the past few days. Nancy pulled up the first.

"Ugh. W-a-a-a-y too old! Good for them still to like fucking at fifty, but I want to see real sexy people. How about the second one?"

I stared at the screen. At least the second couple were in their twenties. "I don't know, Nance, they look a bit extreme. They say they're both bi and want DP and DV and I don't think I'm quite ready for that. Or sucking guys off."

Nancy gave me a regretful look. "Yeah, I suppose. I'm eager to watch, but I'm not sure I want multiple cocks stuck up me right away, either. Darn!"

I had an idea. "How about Portland listings? It's only an hour's drive or so."

Nancy clicked on "Portland, Casual Encounters, MW4MW."

We watched a long list of ads appear.

"Much more encouraging! How about this one?" Nancy pointed.

It was the third ad in the list, dated today. We read the heading, "Friendly, Fit, 20s Couple Looking to Play and Watch, and Maybe More."

Nancy clicked on the details. It seemed to be just what we were looking for:

"Young professional couple, 28 and 26, in good shape, seeks similar for same room sex -- and maybe more, if everyone is comfortable. We are somewhat experienced but happy to play with newbies.

He's 190lb, 6 ft 2, and charming. She's 125 lb, 5 ft 4, with a great body and a lovely smile.

Meet for drinks first to check the chemistry, we hope you'll be our friends.

Interested? Tell us about yourselves, and send pics.

A and K"

Two images with faces cropped out were included, both male and female in swimsuits, hers a bikini with a thong bottom that made me lick my lips.

"She's got a great body," I commented. "And really nice boobs."

"He's got a terrific torso," Nancy countered. She was sensitive about her small breasts. "And great abs." She punched me on my arm. "I bet he's got a huge cock, too."

"Dirty-minded female! So are we ready to respond?" I asked, but the answer was obvious. Nancy was already hitting the "Reply" button.

"Wait, we need to send pics." I reached for my iPhone as Nancy's fingers tapped out the beginning of an email message.

Ten minutes later, we took a last look at our proposed reply. We described ourselves as enthusiastically as possible, attached our pics, in underclothes with faces cropped out, and signed it "N and P." Nancy hit the Hotmail Send button. Now we had to wait.

** *

Four days later, back in Nancy's apartment, staring at the usual garbage emails that had arrived in her Hotmail inbox, we were about ready to give up on our first attempt. There was still no reply from "A and K."

"Just went into a goddamn black hole. We should have replied to more than just one ad," I said. "We were stupid. Though it was probably a scam, anyway."

"Yeah," Nancy agreed. "But they seemed so perfect. Maybe I just thought wanting it enough would make it happen."

"Let's take a look at the latest Portland listings. There's got to be some nice perverted young couple out there, just waiting for us."

Nancy's fingers were just reaching for the keyboard when one more email arrived on the screen.

"Wait! It's a Craigslist address. With the Friendly, Fit, 20s Couple headline."

"So open it!"

I pushed her across the couch so we both could see the screen.

"Hi there, N and P..."

The email from A and K was apologetic, explaining that they'd been trying to set up a date with another couple whose ad reply had arrived ahead of ours, but the couple had chickened out at the last minute.

"We'd have picked you guys as our first choice," the email went on, "but we'd already started to trade emails with the other folk."

"But if you are still interested and available, please reply with a cell # so the two females can verify that we are all real. Then we can meet—maybe Saturday evening—and go from there.

"Love

"A and K."

"Yeah!" Nancy grinned at me. "They'll get a reply right back. Now! And mark your calendar for Saturday, kiddo!"

* **

We found a parking spot in downtown Portland more easily than we'd expected on a Saturday evening and were a few minutes early as we approached the hotel.

Nancy and Karen—we now were all open about our names—had talked on the phone twice since our exchange of emails and agreed we should get together on what Karen called "neutral territory." We would meet in the lobby of a downtown hotel where Karen and her husband Alan had reserved a room. We'd have a drink in the bar before deciding if we were all comfortable enough to go ahead.

Nancy and I were glad of this cautious approach. Now it looked like it was about to happen, Nancy was nervous and I was wondering how well I'd be able to perform in front of another couple.

I took Nancy's hand as we walked into the hotel and felt a slight tremble.

"We don't have to do anything," I told her. "If we don't like these guys, or it just doesn't feel right, we can walk straight out of the hotel. And even when we're in the room, we can still leave if we don't want to go ahead."

"Okay, I guess," Nancy gave me a quick grin. "And maybe everything will be exactly what we're hoping for. If we're lucky!"

We pushed open the door to the lobby and saw the others immediately. We'd still not exchanged facial photos but the smiling couple facing the door had to be Alan and Karen.

The man, tall, dark-haired, and clean-shaven, wearing a smart short-sleeved shirt and tan pants, crossed the lobby with a broad grin on his face and shook my hand.

"I'm Alan, and you're Pete?"

"Right."

Alan turned to Nancy and gave her a quick hug. "It's wonderful to meet you for real." He beckoned to the attractive blonde with shoulder-length hair, in a pale blue silk top over a darker blue short skirt, already moving towards us. "And this is Karen."

A wide smile appeared on Karen's face. She leaned forward to kiss me lightly on the mouth, then hugged Nancy.

"I'm so glad you were able to make it," Karen told us warmly. "Though I feel I know Nancy already just from a couple of phone calls."

"Women telling secrets," Alan laughed. "Let's go in the bar, and learn some more about each other."

Two beers apiece later, it was clear we were all enjoying each other's company. Alan was a salesman for a large electronics firm, and obviously a successful one. As the original ad had claimed, he was charming, with a ready grin, along with a fund of funny stories. More than other salesmen I'd met, he was a good listener, not eager to dominate the conversation, and seeming genuinely interested in what we had to say. And Karen—she was a delight. She had a lovely wide smile and a wonderful musical laugh, able to be totally relaxed with us and putting everyone at ease. She told us she was an emergency room nurse at one of Portland's hospitals, working the day shift and occasional weekends—but fortunately not this one. She too had some funny stories, mostly about the strange things people managed to get stuck in their body orifices, although it was obvious there were others less amusing. She was warm and relaxed and I could imagine her being unflappable in a crisis.

It was as if we'd been friends for years. We talked some more about Alan's and Karen's jobs, and then about Nancy's and my graduate programs (environmental science for Nancy, creative writing for me). The conversation moved on to sports and Alan and I were deep in a discussion about the Portland Timbers soccer team, while Karen and Nancy giggled about experiences at various gyms, when we were interrupted.

"Another round?" Our server had returned and was standing at Alan's shoulder.

"Or are we all ready to go?" Alan looked around the table.

This was it. Nancy and I could leave, or we could head upstairs.

I looked at Nancy.

She nodded, our signal for going ahead. I nodded back, far more comfortable with the evening's possibilities than I'd expected.

"We're ready," I told Alan, with what I hoped was meaningful emphasis.

Alan's face broke into a broad grin. "Great!" He turned to our server. "The check, please."

We shared the elevator with two serious-looking older couples apparently attending some kind of religious convention, while the four of us tried to avoid laughing. Our evening was going to be very different from theirs.

Alan and Karen led Nancy and me to the room they'd checked into earlier. Closing the door behind us, Alan pulled Nancy towards him and gave her a long kiss. "I've been wanting to do that ever since we walked into the bar," he told her.

Karen touched my shoulder, then moved quickly into my arms for an equally long kiss that allowed me to inhale her delicate perfume. As we moved apart, she said softly "I think you're going to enjoy this evening."

"I think so too." I wondered if she'd noticed my stiffening cock as we embraced.

Alan said: "The bathroom's through there." He pointed. "And the minibar is under the TV if we need more refreshment any time." He looked at Nancy and me and laughed. "And the bed's over there!"

The covers had already been removed from the king-size bed. Several pillows were piled at the headboard end, along with a couple of small towels.

"Kick off your shoes and socks and climb aboard." Alan directed. "The show's about to begin."

Nancy and I looked at each other. We might still be a tiny bit nervous, but we weren't changing our minds now.

Alan and Karen moved to the headboard end while Nancy and I plopped down close to the foot. Karen had told Nancy in one of their phone conversations that when they played with "newbies," they usually started the action, "just to set the mood," Nancy had reported to me.

As Alan and Karen arranged themselves on the pillows, Nancy gripped my hand. "God, I've been so wanting to see this," she whispered.

Alan and Karen reached out and embraced, their mouths moving together, lips sliding across each other's. Alan put one hand behind Karen's head and pulled her into a harder, longer kiss. They broke for a moment to smile at us, then continued kissing, mouths seeking mouths, slipping down to the napes of necks, then tongues touching and teasing. Alan moved one hand down to Karen's silk top, sliding his fingers back and forth across where her nipples were now visible through the silk. Karen slid a hand slowly across Alan's body, then down to the front of his pants where the outline of his cockhead was becoming apparent. I saw Alan smile as Karen's hand wandered across his crotch, then he reached for her silk top, carefully undoing buttons. At the same time, Karen managed to get his belt undone.

I felt Nancy's hand grip mine more tightly.

Alan slowly lifted the silk top over Karen's head and dropped it behind her.

I caught my breath as Karen's beautifully filled lacy brassiere appeared. Her nipples were obviously hard, pushing out the delicate fabric that barely contained each breast. Next to me, Nancy whispered: "No drooling!"

Alan wasn't done. He leaned across Karen to undo the buttons on her blue skirt, then eased her up as she pushed the skirt down her legs and onto the bed.

"Lovely underwear," Nancy said quietly as Karen's matching lacy panties appeared.

As Karen smiled in response, I gazed at the damp patch on the panties. My cock was definitely getting stiff.

Now it was Alan's turn. He pulled off his shirt himself, waiting while Karen unzipped and opened his pants, then wriggled out of them to sit back in a pair of dark red boxers with a serious bulge at the front.

I glanced at Nancy. Her mouth was slightly open and her tongue was peeking between her lips.