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Satisfying Cassie’s Curiosity

Category: Group Sex
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It’s been more than a few days since my “Birthday Beach Bang”, but I find myself replaying it over and over in my mind. More than once I have awakened perspiring, with my sheets in disarray. I’ve been reliving that grand adventure in my dreams almost every night. I suppose that my friend Cassie asking me about it almost every day at work might have something to do with it as well.

At my birthday dinner that evening, my girlfriends insisted that I tell them why I was suddenly in such a good mood. I briefly recounted for them what transpired between Jon, Craig, Nick and I in the beach hut. They, of course, demanded all the details. Amy and Karen giggled softly, while Cassie sat and stared with rapt attention. I don’t think Cassie expected to hear such a story from me. Amy and Karen, on the other hand, probably thought it was too tame.

Amy was my college roommate, so she knows me — intimately, actually. She is the one who taught me how to masturbate and how to properly suck a man’s cock. Karen is Amy’s sister, older by just one year. These two are THE most sexually adventurous women I have ever met. I know for certain that my little birthday party with those three college boys was nothing, compared to what they have done.

Cassie is a new co-worker of mine. She is a full decade younger than my 35 years but, despite the age difference, she and I struck up a fast and close friendship. Cassie isn’t totally naïve in the ways of the world, but I would wager she didn’t have anybody like Amy for roommate in college. When she repeatedly found reasons to ask about my birthday soiree, it became apparent to me that Cassie was more than just curious. She wanted something similar. She just couldn’t bring herself to come out and ask.

Sensing that Cassie was seeking out a sexual adventure, I invited her to dinner at my place. I thought that maybe after a nice meal and a few glasses of wine, I could get her to tell me what was really on her mind. It worked better than I thought it would. No sooner had we settled into lounge chairs in my garden than Cassie blurted out, “I’ve been dying to get you alone to ask….” She went on for almost half an hour without stopping.

I was right. Cassie has been hinting strongly to her boyfriend Ben, that she is interested in, what she terms, “a group experience”. It all started after the two of them downloaded some adult movies online. They have replayed them over and over, and fucked each other silly night after night. Now they want to go another step. They just don’t know how to go about it. They also are sure they didn’t want to just fuck some strangers in a swing club. Once Cassie heard about my three-on-one, she’s been trying to figure out some way to ask me to join them. That way she could have someone else she trusted along with Ben.

“Do you think you might …want to?” she asked.

The truth of the matter is who wouldn’t want to? Cassie is a beauty. Her soft, subtle red hair is styled in the newest, short bob. Her eyes are hazel and almost almond in shape. Her petite, 5’5″ frame appears lithe and flexible. Her breasts are smaller than my round 34C’s, but are as pert as can be. They appear as perfect apples, straining against her tight cropped tee shirt. Very low rise, cut off shorts leave little to the imagination, as they accentuate her smooth, tanned thighs and legs. I’ve long ago stopped counting how many men I’ve been with, but you can count on one hand the number of women. Outside of Amy and Karen, there were just two more. Cassie would make now make that total five.

“I think I could be persuaded,” I replied playfully.

“Fantastic!” she exclaimed. “Now, what’s next?”

“Well, we’ll need at least one more,” I told her. “Should it be a man, or a woman?” I asked.

“I think… a man,” she said. “Just in case I chicken out, then you’ll still have someone for yourself. Do you have anyone in mind?”

“Actually, I do,” I smiled. Since my birthday, I just can’t stop thinking about Jon. Now, all I had to do was find him. I only hoped he would want to as well.

We decided we would get together this Friday evening. I love to cook for company, so we could eat dinner here. Dinner conversation could lay the foundation for the rest of the evening, without worrying who might overhear. If everyone was comfortable, we could continue without interruption. With all the little details settled, I bid Cassie goodnight, resisting my newfound urge to pleasure myself with her right now. Despite wearing out the batteries in my vibrator before falling asleep that night, my dreams were even more vivid than before.

I got up early the next morning and made my way to the university. I didn’t know Jon’s last name, or where he lived. I was certain, however, that if I staked out the student union, he would eventually show up. What wasn’t certain was what his reaction would be to seeing me again. Would he remember? Would he be interested? Would he freak out and run?

I waited about an hour, and then I saw him. I also noticed that, apparently, I was not the only one hoping to see him. At the next table, two cheerleaders were cooing and whispering to one another about him. The competition was younger than I was, and they weren’t playing fair. How was I supposed to compete with their tight little sweaters and short skirts?

Well, they may be younger, but experience was on my side. Besides, I’ve already had my way with him. What did I have to lose? I got up and started to make my way over to where he stood. I heard my competition make a few disparaging remarks about my age and my nerve. I ignored them. I walked right up to him and tapped him on the shoulder.

The moment he turned around to face me, every eye in the room was on us, because he practically screamed, “Shannon!” He hugged me, kissed me, literally picked me up off the ground and held me. “I can’t believe you’re here.”

“As much as I enjoy you holding me, Jon,” I teased, “it would be easier to talk with you if you put me down.”

“Sorry,” he said. He put me down, but didn’t let me go. He held both my hands, as if I would, any minute, disappear from sight. We sat and talked quietly about what transpired between us and since. Before long, I asked him if he would be interested in having dinner with me, Cassie and Ben. It was easier than I thought to ask him. I guess after a guy pumps two loads of cum into you in one afternoon, asking him to dinner is not all that difficult.

“Will it be just dinner, or something more?” he asked.

“Definitely dinner, but hopefully something more as well,” I confessed. “The something more is completely up to Cassie and Ben this time.”

“Well, I was just hoping to have dinner with you,” he replied. “But if Cassie is such a close friend or yours, then who am I to argue? “I would love to see you again.” He kissed my hands.

“Great,” I said. “Here is the address, and my phone number. Dinner is at six. Something more will follow shortly, even if it’s just the two of us.” He kissed my hands again. Reluctantly, I let him head off to class, but this time when he left me, I knew I would see him again soon. On my way out, I stopped by the competition’s table and slyly said, “Now that’s how you make a date, girls.”

I had two days to prepare. I shopped for groceries, tested recipes, and picked out several of my favorite wines. I cleaned my house within an inch of its life. I also made sure the privacy fence around my garden was intact, just in case our something more spilled outdoors. Finally, Friday evening arrived.

After getting dinner in the oven, I headed for the shower. As a personal preference, I shave every hair from my body, except for those on my head. This being an extra special night, I made sure to pay special attention to my delicate mound. My body wash was new, and the scent of lavender always brings out my passionate side. Before long I found myself fantasizing about Cassie, remembering Jon, and wondering about Ben.

Overcome with desire and anticipation, I slid in my favorite butt plug and turned on its vibrating bullet. I slowly masturbated, as the warm water cascaded over by breasts and down to my clit. Soon, I was furiously rubbing my swollen clit as the bullet in my butt plug unceasingly throbbed. The orgasm was sudden and I tensed against the pleasure plug in my ass. I thought about bringing on another orgasm, before deciding I could wait until later, when I was no longer alone.

I finished my shower and dried off. I got my hair and makeup ready, and then slipped into a little sun dress. No real need for a bra and thong tonight, so why bother with them? I wondered how long it would take my dinner guests to notice. Not long, I hoped.

Cassie and Ben arrived first. While Ben was looking over the house, I was looking over Cassie. She also was wearing a tiny sundress. It was easy to see that she also shirked wearing a bra tonight. When Ben made his way to the living room, I unabashedly lifted the back of her dress over her ass and saw the barest string thong nestled between her tight round cheeks. She stifled a gasp, and playfully slapped my hand.

“Later,” she whispered. “It’s bad enough I had to fight Ben off in the car.”

“I’m sorry,” I said, as I pulled her dress back into place.

“Don’t be,” she whispered. “I’ve been wondering how to get you to do that, almost since the day I met you.”

I kissed her lightly, and then took the time to smooth her dress over her luscious backside. Over her shoulder, I caught a glimpse of Ben. He wasn’t much taller than Cassie, certainly shorter than me. His blond hair was close cropped, his blue eyes bright. His build wasn’t muscular, but he was not slight either. His smile was infectious. I smiled at the thought of both of them, but I could feel myself moistening knowing that I would soon be with Jon again.

The doorbell rang and my heart actually skipped a beat. I stood there looking down the hallway at the door, but my feet seemed riveted to the floor. Cassie playfully spoke into my ear, “If this guy has that much of an effect on you, then I can’t wait to meet him. I’ll get the door.”

She opened the door and there stood Jon. He wore a black shirt and tie over ivory chinos. He seemed the most handsome man I’ve ever seen. In his hand he held a bouquet of fresh flowers. I finally remembered how to walk, went to the door and invited him in. There was a gentle smell of musk on his neck as he kissed me. I made the introductions, put the flowers in a vase on the table and started to get dinner on the table. Jon made himself immediately at home and poured wine for everyone.

After dinner, more wine was poured, and we all seemed to silently wonder just how soon the rest of the evening would commence. I picked up my wineglass, kissed Jon on the cheek and asked him to join me in the living room. We made our way to the sofa, and sat. I snuggled up as close as I could and made myself comfortable in the crook of his shoulder. After a brief, whispered conversation, Cassie and Ben followed us. Cassie fidgeted in the overstuffed chair directly opposite us and Ben perched himself, uncomfortably, on one of its arms.

“Well,” I said. “What shall we do with the rest of the evening? I know that you and Ben were interested in something new, but what exactly would you like to happen?”

“I’m still a little nervous,” Cassie confessed.

“That’s alright,” I reassured her. “We don’t have to rush into anything. The night is all ours. Let’s just see where it takes us. We each have a mate of our own we feel comfortable with, so I suggest we start there.”

I put my wine glass on the coffee table and spun around to face Jon. I loosened his tie and began unbuttoning his shirt. I took my time kissing his face and his chest, this being quite a bit different from our first encounter. I soon had his shirt off and began loosening his belt. I stole a look at Cassie. She was mesmerized. Her own live action show was unfolding just a few feet from her.

Ben was rubbing one of her breasts. She was rubbing the other. I mouthed the words, “It’s OK,” and began to remove Jon’s pants. His cock was already semi erect and I marveled once again at its size. Cassie let out a barely audible gasp. Jon reached up and slid my sundress over my head. I was instantly naked, and I heard another gasp from Cassie.

I looked over to see that Ben was now naked as well. He was stroking his cock, encouraging it to reach its fullest. He was not nearly as long as Jon, and not as thick. I smiled appreciatively at his nakedness, and purposely starred at his growing erection. He now seemed unconcerned with comparing himself to Jon. He swiftly relieved Cassie of her dress. She looked amazing, standing there wearing only the skimpy thong, before Ben relieved her of that as well.

Her breasts were just like the perfect apples I envisioned them to be. They were pert and stood out proudly from her chest. Her mound was topped by a perfectly sculpted V of red hair. She had the palest areolas that covered almost half of each breast. Her nearly as pale nipples were just beginning to harden. My dark nipples were as hard as ice as I took in the vision that was Cassie.

I reached down and grasped Jon’s now sturdy cock. I alternated stroking and licking it while he massaged my breasts. I stole glimpses of Amy and Ben and saw that they were matching us stroke for stroke. This could be fun, having little sexual protégés learn from me. I guess being the oldest in the room has an upside after all.

With a renewed vigor, I quickly took as much of Jon’s cock down my throat as possible. He let out a moan to encourage me to continue. I bobbed my head up and down over his hot, hard shaft, while rhythmically stroking it with my hand as well. A few gagging noises from Cassie told me that Ben was now down her throat too. My clit gave a little throb of desire.

Soon, both Jon’s cock and my slit were dripping wet. I gave one final slurp and stood over him. I faced away from him, toward Cassie and Ben. As I lowered myself onto Jon’s rampant erection, I watched Cassie begin to position herself similarly over Ben.

“Come closer,” I pleaded. She took Ben by the hand and guided him to the floor near where Jon was on his back, slowly drilling himself in and out my eager slot. Finally in position, Cassie took Ben deep into herself and began to vigorously bounce on his spirited cock.

“Slow down, and try to match our rhythm,” I said. She understood and before long, the four of us were almost as one. When Ben took over their thrusting duties, she began to massage my heaving breasts. Her first touch sent a shiver through me. I clamped Jon’s cock in my slot tightly, and arched my back to increase the feel of Cassie’s hands on my body. Another shudder and Jon quickened his pace. Ben, sensing this, increased his pace as well.

Cassie let out a loud moan, as the first orgasm ripped through her. She stopped rubbing my tits and firmly grasped her own, as she ground her clit onto the base of Ben’s cock. The sound of her pleasure triggered my own orgasm and I let out a similar cry. Jon responded by driving himself fully into me and holding me down on his hilt. I clamped down on his cock as hard as I could, as a second orgasm rolled over me, right on top of the first.

Ben lost all sense of rhythm and started pounding Cassie’s cunt hard and fast. Her moans were now a continuous, guttural cry of ecstasy which only further spurred Ben’s pace. Not to be outdone, Jon began to forcefully ram his enormous cock into my hot, and now dripping, slot.

Cassie’s repeated orgasms had her out of her mind. “Fuck me, fuck me,” she repeated through gasps and moans. “I’m cumming again. Harder! Faster!”

By this time, I didn’t have much more control than she did. However, orgasms turn my speech into gibberish, so nothing intelligible was heard in my cries. My juices ran freely out of me and flowed all over Jon’s bare shaft and balls. The increasing moisture between us added another layer of harmony to the chorus we sang, as four naked bodies slammed against each other repeatedly.

“Cassie, honey,” I managed to say. “Don’t let him cum just yet. I want to watch.” I think she moaned in the affirmative.

Another few thrusts and Cassie disengaged from Ben. He stood quickly and started pumping his shaft as Cassie knelt in front of him expectantly. I managed, with some difficulty, to stop Jon from fucking me. I knelt next to Cassie as Jon came over and stood before me. I took over pumping his cock for him and impatiently waited for him to cum. Cassie did the same for Ben. I began to fondle Jon’s balls with my free hand and lick his helmet encouragingly. I could feel the orgasm building in his cock, as it swelled in my grip. I looked up at him and gave a wink. He smiled back at me mischievously, as he realized what I was about to do.

Cassie was intently stroking Ben’s shaft and never saw me turn Jon’s toward her. A hot, white rope blasted out of Jon’s cock and draped itself over Cassie’s fabulous, firm breasts. Cassie inhaled audibly. A second bullet of steamy cum followed the first and drove itself into the valley between them. Ben opened his eyes just in time to see Jon’s third shot of cum nearly obliterate Cassie’s left tit from view. Seeing his girlfriend’s tits covered in cum was all it took to finish him.

Ben’s first shot hit Cassie squarely on the chin. Cassie, in turn, aimed Ben’s cock at me and I felt blast after blast of hot cum hit my tits and neck. I continued to pump every drop of cum out of Jon’s balls onto Cassie. She returned the favor to me with Ben’s, the four of us reveling in the warm, white crossfire. When they had shot their last, the boys appraised their work and seemed satisfied. Each had decorated the other man’s lover with his own cum. Their now sagging cocks looked in need of rest. Our men were spent, but Cassie eyed me hungrily.

“Have a seat boys,” I said. “We’ll take it from here.”

We turned to face each other. Cassie’s tits were covered in Jon’s wondrous, white wad. A small stream was making its way over her stomach to join that which was already pooling in her little, sculpted, red tuft. Some of Ben’s load was similarly seeking out my completely shaved mound, while most of it clung contentedly to my breasts.

From my position on the floor, I was able to reach under the sofa and take out the elegantly wrapped gift box I placed there before anyone arrived. “A little something for all of us to share,” I said, as I slid the box toward Cassie. “Open it.”

Inside was a small treasure trove of new toys I purchased, specifically for this evening. I wasn’t sure what the others might enjoy, so I bought a varied array just to be sure. As Cassie began unwrapping the box, a large dollop of cum dripped onto the package.

“Here, let me help you with that,” I said. I moved closer to her and proceeded to lick Jon’s cum from her body. She arched her back and heaved her tits towards my eager tongue and lips. The sweet flavor of Cassie, mixed with the salty tang of Jon, was indescribable. I hungrily cleaned almost every drop from her tits and made my way down her flat stomach to her moist red mound. As I started to lick her swollen clit, I stopped. A look of disappointment crossed Cassie’s face.

“Don’t worry, Cassie,” I whispered. “I’m not done with you yet.” I took Cassie, and the toy box, through the sliding glass door, into my patio garden. She looked around nervously.

“There’s no need to worry,” I told her. “I sunbathe out here regularly, and always in the nude. Those hedges and that fence will make sure we are not interrupted. Now, let’s see what we have in here.” I took out several of the toys in the box and showed them to Cassie. The one that made her eyes open wide was the strap-on.

“I’ve always wondered what it was like,” she confessed.

“Only one way to find out,” I offered. “Ladies choice. Give or receive?”

“Receive,” she said softly.

I opened the package and began to belt on the harness. I took the long, narrow shaft and rolled it over and between my breasts, coating it with Ben’s cooled, thick cum. All the while, Cassie sat on the edge of the lounge chair, her fingers rapidly circling her clit. Every so often, she would slip two or three inside her slot and continue the circling motion. I set the dildo in the harness and tightened the straps.

Cassie turned and knelt on all fours upon the cushioned lounge, offering her swollen, dripping slot to me. I took the cum-coated dildo and toyed with her vaginal opening. I continued to penetrate her slot by no more than an inch, before backing out and rubbing her clit with the soft, jelly head. She writhed in anticipation, until one more time, when I just entered her slit, she backed into it with such force that it plunged into her completely.

Cassie leaned forward, and then pushed back repeatedly. I grasped her slender waist to steady myself against her powerful thrusts. She uttered soft grunts every time her little, round ass contacted my thighs, the dildo buried deep in her insisting slot. Reaching around her, I resumed the circular massage of her clit. My own level of desire was rising. I now wished that the dildo was double headed, so that it would plunge into me as well with each of her vigorous strokes. I could feel her moisture beginning to dampen my thighs, as she continued to pleasurably punish her cunt with my strapped on cock.

“I’m going to cum,” she cried.

“Then I guess I arrived just in time,” Jon laughed. We were so busy with each other that neither of us heard him come outside. “Please, continue,” he said, “I was really enjoying the show.” The sight of his livid erection was proof enough that he was truly enjoying it.

Cassie continued to masturbate and mewl softly as the orgasm built inside her, but it seemed to refuse to crash over her completely. “Shannon,” she pleaded breathlessly, “Would you mind …if …Jon finished me off? Please.”

Jon looked at me and I sensed some degree of worry. “Jon,” I said, “Be a dear and help her out.”

“It’s OK with you?” he asked.

“Well, I do have one condition,” I admitted. I whispered my intentions in Jon’s ear. He turned to look at me, his eyes wide with surprise and wonder. With a sparkle in my emerald green eyes, I stared back at him, bit my lip impishly and shrugged.

A resigned smile formed on his ruggedly handsome face. “If those are the rules, then those are the rules,” he laughed. “I always play by the rules, Shannon. Knock yourself out.”

By now, Cassie was literally squirming on the padded lounge chair. Jon positioned himself behind her and lifted her lovely ass to his hard, thick cock. He slid her juicy slit along his shaft and coated himself with her juices. It took some effort to get her to stop squirming. She would have to relax a bit if she hoped to accommodate his massive cock into her tight, little cunt.

Patiently, he started to push himself into her. Small thrust after thrust, his cock inched his way fully into her wet slot. Cassie was now panting heavily. The pitch in her voice went up a notch as Jon began to pound himself into her with some authority.

“Ready when you are, Shannon,” he grunted without breaking stride.

I kissed the back of his neck and lightly rubbed his broad shoulders. I grazed my fingernails down his strong back. Jon groaned only a little as I thrust my pelvis forward and my strap-on slid deep in his ass. It was still coated with Cassie’s thick juice and, as such, I could thrust it in and out of his ass with relative ease. I mirrored Jon’s thrusts into Cassie with thrusts of my own. Pleasure moans from both of them echoed in my ears.

“Fuck me, fuck me, fuck me,” Cassie cried at the top of her voice as an orgasm tore through her.

Jon did his best to comply and relentlessly drove his cock into her writhing body. I felt Jon’s back stiffen and then his orgasm practically pulled my dildo out of the harness. I could now feel his pelvic muscles pulsing rhythmically. I felt each pulse radiate up the shaft of the dildo as he pumped Cassie full of cum. Each pulse rubbed the base against my swollen clit and an orgasm finally crashed over me.

Our climax built, hit its crescendo, and slowly lapsed. Cassie collapsed in a sweaty, cum dripping heap onto the lounge. I leaned into Jon’s back and wrapped my arms around his waist. He turned to face me, held me tight, and kissed me as he did that afternoon in the beach hut.

When we all finally caught our breath, we saw what a picture our little threesome must have made. Ben stood fully naked in the living room, behind the closed sliding glass door. He was staring out at us, a vacant smile plastered on his face. He was still absent mindedly stroking his flaccid cock, as cum slowly dripped down the glass door.

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