First time Swinging (MFM, Swinging, First Time, Anal) | 2016

In the long lost days of yore, those days of AOL "Chat" rooms, I spent a couple months in a local area swingers chat, getting to know some folks. I'd tripped across it while talking to someone, and hung around because the conversation was fun and the innuendo heavy. I'd made some online friends in this room, something not easy to do for a single male, or so I'd been told. Maybe it was because I really wasn't looking to hook up that gained me some acceptance, but for whatever reason, I was soon considered a regular. So it shouldn't have come as a surprise when I was finally contacted by a couple and asked if I wanted to meet them for "Drinks and...", the "And" being left open ended. I admit, I was very nervous about the possibility of meeting anyone in the Lifestyle in person, but decided life's not too short not try it even once. We agreed to meet in a nice area of town, full of wine bars and outdoor cafes'. I was slightly anxious, so I'd gotten there early to scope the place out and get a good place to sit and people watch. After 10 minutes or so, I noticed the couple I was expecting, and my position at the back of the bar let me get a good look at them as they moved towards me. They were a middle aged couple, casually but well dressed. He was tall, 6' to 6'1", and slender in build. He had dark thinning hair and a high widows peak, hair combed straight back. He guided his wife through the maze of chairs with a hand on her back. She near matched him in height, being close to 6 feet in her heels. Black hair like her husband, cut in a cute but expensive looking bob that accented her long pixieish face. She had a sort of bemused look on her face and a slight grin, like a cat who hadn't decided if she was going to play with the mouse first, or eat it right then. She had green eyes I was pretty sure weren't contacts, and a tight figure that indicated a lot of time in the gym. She obviously spent a good amount of time tending to her figure. She wore a simple yet elegant little black dress, a string of cultured pearls around her neck, and matching earrings. The pearls hung down to just above her exposed cleavage, which I suspected were augmented. They made a very attractive couple. Everything about them said upper middle class professionals. Well off ones. I stood up at their approach, introducing myself and telling them I was glad to meet someone from the chat room. We settled in and ordered drinks. Craft beers for the gentlemen, and white wine for the lady. We chit chatted for a while, getting to know each other, talking about the doings in the chat room, and who we knew in the lifestyle. I made it known I was completely new to the lifestyle, and had no experience, but had made a few friends. They owned an auto dealership, and had a house in a very nice part of town. I got even more nervous, since I was very much a blue collar guy. After about 30 minutes of drinks and conversation, the couple exchanged a look, and her husband excused himself to go to the men's room. As he did, he bent over and laid a kiss on his wife that got the room's attention. Deep, long, passionate, with lots of tongue action. The room temperature seemed to shoot up 20 degrees. I felt like applauding when they came up for air, and I know it was hot enough to start my dick to swelling. I'd be happy just to WATCH these two fuck, if that's all that came out of the evening. They were clearly into each other and passionate lovers. When he sauntered off to the restrooms, she had another sip of her wine and then turned to me and said, out of the blue, "Kiss me." I admit, I panicked for about a half second. A million things shot through my mind. Was I being set up for a jealous husband scheme? Was she going to slap me and call the cops? Mentally, I slapped myself back into sanity and leaned in to kiss her. Gently, even chastely, to begin with, but as the pressure of her lips increased on mine, I felt them part, and the tip of her tongue part mine. Then I threw caution to the winds and went for it, trying to match the thrust and parry of her tongue with my own. After 30 seconds or so of fencing with our tongues, we called it a draw and separated. Her husband stood leaning on the wall by her shoulder, grinning, and as I looked around the bar, I saw the faces of the other customers, some scandalized, some wondering, and one or two that looked like they knew the score and approved. She sat back, looking like a cat who'd gotten the cream, and licked her lips. She turned to her husband, who had his hand on her shoulder, and said, "Oh yes, he'll do nicely. He kisses so well."
That was when they invited me to "play" with them, and invited me back to their place. She must have noticed my nervousness, and suggested they could go to my place instead. I agreed, and we paid our respective tabs and headed for our cars. At the last minute, she decided to ride with me, her husband following. No problem, I thought to myself. As we drove to my condo, she continued talking to me about swinging, putting me at ease. At the same time, she shrugged out of the top of her dress, saying, "You've been staring at my tits, all night, so you might as well have a good look." I was right, she'd had them done, but they were very well done. In fact, they were magnificent. She'd gone for a 38 C cup, large but not overwhelming. They hung perfectly naturally, capped by gorgeous tan nipples with areolas the size of half dollars. And being a cool night, her nipples were standing at attention. As best I could while driving a stick, I reached across and caressed her tits, giving her erect nipples a little tweak. She hissed through her teeth, telling me she loved her nipples pinched, as her hand slid into my lap, and she started stroking my cock through my slacks. We were both breathing heavy when we pulled into the lot in front of my place, and her husband got out of his car, grinning from ear to ear. He evidently knew his wife well enough to know what she'd gotten up to.

We went into the condo and headed straight for my bedroom and my king size bed. She excused herself to the bathroom with her purse, telling us men she was going to get comfortable. Then she disappeared behind the door. He and I sat on opposite sides of the bed, and stripped down to our shorts and for some odd reason, left our socks on. And we continued to sit there, making VERY awkward small talk, waiting on her. 5 minutes later (Though it felt like an hour), she swept out of the bathroom and into the candlelit bedroom, wearing a tiny black teddy, and burst out laughing. At us. "What are you two going to do to me still dressed like that?" she laughed, and that was all the ice breaker we needed. Her husband, closest to her, swept her up in his arms and lowered her to the bed, raining kisses on her mouth and throat, working his way downwards. He freed her breasts from the teddy by pulling it down, roughly, and offered me the one closest to me. Together, we licked, nibbled and kneaded her tits until she was breathing heavy. Then he disappeared downwards, sliding between her legs with his face. I could see she was completely shaved, and as his tongue hit her pussy, she gasped and closed her green eyes. I continued working on her tits while watching him lick her pussy, until she whispered, "I need something in my mouth", and reached for my dick. I scooted closer, and slid my cock between her lips. She was very good, tickling the head of my cock with her tongue while working the shaft in a steady rhythm, humming to herself while she did so. Suddenly, she clamped down on my cock with her mouth and her hand, and the humming stopped. I looked down, and her husband was licking her clit at a good clip, fucking her with two fingers of his left hand. She was coming, and her whole body shuddered when she did. a few seconds later, he and I switched places, and I went down on her. She was soaked from her first orgasm, and her clit was still sensitive. I decided that that wasn't going to deter me, and I went for her pussy like a man dying of thirst at an oasis. I licked all around her inner thighs, slowly circling my way towards her outer folds, then separating each one and licking it until they blossomed like flower petals, giving me access to the interior of her wet pussy. Slowly, while just licking her clit with the top of my tongue, I slid my fingers inside her, gently probing for her G spot. Once I hit it, she gave a convulsion and a gasp, and I looked up her body to her face. Her husband had his hands on either side of her face, and was holding her still while he pumped his cock in and out of her face. He was slightly longer than me, but I had more girth. Together, we were driving her crazy. I returned to her pussy, and started sawing my fingers into her pussy, making sure to rub against her G spot as often as possible. At the same time, I sucked her clit into my mouth, running the flat of my tongue over it in a clockwise fashion, pausing ever few rotations to tickled it with the tip of my tongue. I could feel her orgasm building before it exploded, her pussy clamping down on my fingers as her back arched and she screamed her pleasure into her husbands dick, while he kept fucking her face.
We took a short break to allow her to catch her breath. I left the room, now completely comfortable being nude around them, and got some wine for those that wanted it. As we sat around having a drink, she was almost purring with pleasure. We talked, and laughed, until her husband announced, "It's time you got fucked, well and proper." She agreed wholeheartedly, and stripped off the teddy, and lay back, hanging her head off the side of the bed. Her husband had the honors, and slid his dick into her pussy long and hard, making her gasp with pleasure. Taking her open mouth as MY cue, I slid my cock into her mouth, and before long, was face fucking her down her throat. Her husband and I set up a matching rhythm, and with her hands caressing my balls, it wasn't long before I was getting ready to come. I could tell by the sounds he was making that he was too, and I announced to them both that I wasn't going to last much longer. She pulled my cock out of her mouth long enough to announce, "Come all over me!" before shoving it back in as far as she could go, almost choking on it. He pulled out of her pussy and came, spurting ropes of semen all over her flat stomach. I was a second behind, starting to come in her mouth, and spraying my cum all over her tits and throat. It was so very erotic, and the most intense thing I'd seen or done up until that moment. Again, we took a rest. She cleaned up, we drank some more, and I figured the night was winding down. I didn't get to fuck her, but I really didn't care. But then, while he and I were reclining on the bed, she reached down and grabbed both our cocks, and started stroking them. Then, on her knees, she began blowing us both, alternating between the dicks in her hands, her ass prettily up in the air. By now we were BOTH hard as iron rods, and since he got to fuck her last time, they both agreed it was my turn. So I pulled out a condom, and she slipped it on me, then climbed aboard, cowgirl style and began riding me. Pretty soon after, I lost track of her husband, because we'd set up a really good rhythm, with me arching my hips upward as hers descended, our parts slapping together loudly and wetly. But she soon slowed, and we settled into a slower deeper pace, her leaning forward onto my chest, her tits pressed against me, bouncing her ass up and down on my cock. I was then I felt her husband climb onto the foot of the bed, between my spread legs and behind his wife. I looked over her left shoulder to see him with a huge grin on his face, as he spread her ass cheeks and slid his well lubed cock into his wife's ass. So THAT'S what he'd been up to! The look on her face as she accepted two cocks, one in her pussy and one in her ass was one of sheer pleasure. She was panting like a bitch in heat, and thrusting back against the cocks that impaled her. She was determined to get as much pleasure as she could out of us, and we were determined to give her every inch! For what seemed like an hour we pounded her in her holes, until her husband stopped thrusting and looked over her sweat covered back and asked me if I'd like a go at her ass. She got that cat like grin on her face again. Now, I'd fantasized about fucking a beautiful woman's tight ass many a time, but never had the guts to suggest it to my limited circle of lovers. And here it was being offered up on a silver platter! Of course I said yes!

A brief moment of flailing arms and legs, and we switched positions and I put on a new condom. She handed me the tube of lube, and coached me on the best way for me to fuck her ass. I couldn't believe this was happening. So I lubed up my latex covered dick, and waited for her husband to slide into her by now soaked pussy. Once he was in, She reached back and spread her ass cheeks wide, saying, "Fuck my ass. Fuck it hard." That was all the encouragement I needed. She still had a little gape from her husbands dick, and though I had more girth, I had no trouble getting the head of my cock past her asshole. It slid in with a pop that made us both gasp, and I could feel her asshole expand and grip my cock. I moved slowly, matching my thrusts to her husbands, until we reached a system that had her rocking like a small boat in a typhoon. Pretty soon she'd loosened up to the point where I could straight up pound her ass as hard as he was pounding her pussy. I could feel her orgasm building again, and when it hit, her ass clamped down on me like a fist. No way was I lasting after that, and evidently, her pussy did the same to her husband. She threw her head back and screamed as the orgasm hit her, and we all pretty much came together. I'd NEVER cum like that up until that point in my life, and it was amazing. We collapsed on top of each other, he in her pussy and my cock still in her ass, gasping for breath. Eventually, our dicks shrank back to normal, and we popped out of her respective orifices. We separated, and she fell back on her back, soaked and satiated. I could see the thin stream of cum oozing from her pussy. Her husband leaned over and kissed her, telling her how much she loved her. We rested, and they borrowed my shower to clean themselves up. I lay in my bed wondering what sex truck had just run me over. Cleaned up and dressed, they thanked me for a wonderful evening, and let themselves out, but not before they told me that I had permission to play with her alone anytime I wished. That was a huge honor, and I told them so.
From that point on, I guess they told their friends, because I was accepted into the community with open arms. And legs.

*That's my story, and every word is true. I hope you enjoyed it, and I will post other experiences if results warrant it.