A Lost Bet Ch. 08

"Don't worry Jo," Alex reassured me with a gentle smile. "We'll take it real slow. But you may want to start lubing up and doing your 'stretching' exercises."

"Yeah Jo, and we'd be happy to help you out," Maria chimed in. Quickly she came over and took one hand while Chantelle took the other. "Charlene, be a dear and grab some lube from over there near the wall." While Charlene went to follow Maria's instructions, she looked at me with a worried look on her face. I returned the look with a subtle nod indicating that everything would be okay.

The girls led me over to the chest and got me settled over it like I was laying across someone's lap. Chantelle slid my skirt down my legs, caressing them lovingly all the way down. "You know you have beautiful legs. I could almost eat them up." Then she gave a quick kiss on each cheek before Charlene handed her the lube. Maria knelt down in front of me and gave me a deep tongue kiss, distracting me from the cold lube being spread on my ass.

"Mmm," Maria intoned through our kiss. "You taste like strawberries." I smiled at that and returned her kiss with a playful nip. "Now are you feeling okay back there?"

"Yes, Chantelle has very soft hands," I replied.

"Okay, then she's going to start stretching you out," Maria started to describe what Chantelle was going to do and, out of the corner of my eye, I could see Charlene looking on with a mix of awe, nervousness, and a little bit of fear. "Jo, what Chantelle is going to do is use her hand, okay? Just nod." I nodded. "She'll start one finger at a time, until she can get her hand in there...then her fist, and by then, you should be plenty stretched for Alex and Mark, okay?" I nodded. "I'm going to stay right here next to you and if it gets to be too much or if she starts moving too fast, I just want you to squeeze my hand, okay?" I nodded.

I closed my eyes and started to lose myself in the sensations of Chantelle's hands on my butt. She wasn't rough in her technique...not that I'd expected her to be. But it's just, she was straightforward about getting her hand in either. She took her time with one finger, sliding it in and out, slowly, gently, and from different angles...tickling my prostate...curling the finger and pulling it out...every move measured against the reactions she drew from me. The thing was, she didn't just focus on her hands connection to my rear. With her other hand she caressed each cheek, sometimes running her hand all the way down my thighs to tickle the backs of my knees. It was such an odd sensation when she would do that with her fingers still inside me because I got confused about where I wanted to move to or how I wanted to move. When she added her second and third fingers, I couldn't help but moan. Unconsciously, I started to rock against her hand, but I gasped in surprise when I felt her bite my cheeks. I didn't think she drew blood, but the sensation set off sparks in my head. The spankings that she mixed in left me reeling and dizzy...not because they were hard enough to really hurt, but simply because the sensations came out of nowhere. I think I gazed out of half-closed eyes momentarily to see Maria smiling at me and licking her lips. I could still feel her hand in mine, but when I searched for her other hand with my eyes, I found it hidden in her own panties and I could see she was enjoying herself almost as much as I was. She gave a gentle squeeze when she saw me looking and I smiled at her.

Apparently Chantelle saw our brief interaction and decided that I needed a little more...distraction, so she abruptly inserted her fourth finger into my rear eliciting an audible cry. Still, she didn't rush it after that. She gave me a few moments to adjust and wiggled her fingers just to hear my breathing get ragged. Slowly and methodically, she continued to slide her hand in and out, filling me...stretching me...making me feel sensations that I couldn't describe, only experience. As I got acclimated to her hand, I couldn't help but rock back and forth with her rhythm. But just when I thought that I had reached the pinnacle...that I could start to really relax and let myself go, Maria whispered to me "one more finger to go, then the hand...then she MIGHT let you come." I nodded as best I could and let myself slide back into that mental and physical cloud that was supposed to be carrying me to ecstasy.

"Here we go," Chantelle said. And with that, I felt her pull out slightly and change her hand position so that all five fingers were teasing my sphincter. Her hand slid in until there was resistance...a silent "O" on my face the entire time...then as I relaxed, further and further in... Maria reminded me to breathe because I'd apparently forgotten to do so while focused on Chantelle's hand. Seconds seem to stretch into minutes and my ass felt fuller than anything I'd experienced thus far. Finally, the pressure eased and I could tell that Chantelle's hand was fully inside me. I could feel her moving her fingers around, and when she actually made a fist, I damn near cried. It seemed like every sensation I had was centered there. I didn't even feel the trunk under me. I was only vaguely aware of being pulled back from the trunk, guided by Chantelle's hand.

"Open your eyes Jo," Chantelle told me. Slowly I opened them and as I did, I saw Maria positioning herself below me. She had stripped off her clothes (although I had no idea when she'd had time to do that) and had slid under me. Chantelle raised her hand and cantilevered me down to kiss Maria's welcoming mouth. As we kissed, I felt more movement near my groin. But it wasn't Chantelle's hand in my ass that I felt. It was her other hand stroking my penis... I'd been so focused on what she was doing to my rear that I'd forgotten I even had one. Slowly she stroked me, letting the silky softness and gentle touch of her hand massage me to a hard state. Maria and I continued to kiss and I started to lose myself again in a world of warm sensations that I had tasted over recent days, but had never really experienced before.

Chantelle used her hand again to guide me lower, forcing my legs straighter until I started to feel a different warmth on the tip of my penis. It was then that I knew that she had positioned me right at the entrance of Maria's vagina. I could feel Maria start to shiver beneath me as my penis twitched against her labia and involuntarily jerked up towards her clit. As we continued to kiss, I could hear Maria moan lightly.

As if that were a cue, Chantelle pushed her arm further into my ass, forcing me down and in to Maria's waiting embrace. An indescribable sound escaped my lips as I entered Maria. It had been so long since I'd been with a woman (instead of "being" the woman) that I'd almost forgotten what it felt like. But Maria's warmth...the way she fit me like a glove and used her muscles to clamp onto my penis...it was like riding a bike and I remembered the beauty of sexing a woman.

I was still at Chantelle's mercy though. With her hand in my rear, she dictated the speed and pace of my thrusts into Maria. It's like she was using me as a dildo to fuck her girlfriend. Not that I minded. Each push and pull and squeeze and release elicited sounds from Maria and from me...sounds without words, but speaking of passion and excitement and feelings of pleasure.

I thought that I heard the guys whispering something in the background but I had no clue. The focus of my world was being used by Chantelle and Maria...no, not used...accepted or included in the lovemaking experience maybe. I didn't know. I could barely think. All I knew was that I was enjoying one of the most fulfilling (and filling) sexual experiences that I'd ever had.

Chantelle changed her hand's position in my rear to put pressure on my prostate and I knew that I would not be long in cumming. Oh, the feeling of cumming inside a woman was something that had been too long in coming. From Maria's vibrations and moaning, I could tell that she was already well on her way over the brink of ecstasy. A few more seconds of Chantelle's pumping me into Maria and I was sent over the cliff as well...crying out...tensing up...shuddering uncontrollably...and tightening my ass around Chantelle's wrist. Until finally, I was done. Of course, Maria continued vibrating for a few moments, clutching onto my penis with her muscles like her life depended on it. Every little movement of Chantelle's hand in me caused me to move in Maria and set off a new round of fireworks for her (I think I actually saw sparks of color in her eyes when they rolled back in her head).

As I lay there on top of Maria trying to catch enough breath for both of us, wrapped in Maria's arms, I felt pressure behind me. "Hold still," Chantelle said as she straightened out her hand and slowly removed it from my rear. "Did you enjoy that?"

I nodded. I tried to speak but apparently my voice wasn't ready to work yet.

"Good, good," Chantelle said as she caressed each butt cheek. "Well, don't get too comfortable yet. I think the guys are ready for their turn."

My eyes snapped open at that. In all the pleasure for being with Chantelle and Maria, I'd managed to forget the original plan. "Do we have to do it now? Can't I just lay here with Maria for awhile?"

"No baby," Chantelle responded. "You probably ought to 'get your ride on' now while you're still stretched out and can accommodate them both."

Some of the nervousness returned, but it was overwhelmed by the warm afterglow I was feeling and the soft touch of Maria's hands on my back made me feel safe enough to go for it.

"Okay, okay," I mumbled from my after-sex haze. "Let's do this."

"Alright, gentleman?" Chantelle turned to Alex and Mark who had already taken off their shirts and looked like they were ready for action...if I was judging the bulges in their pants correctly from my vantage point.

"Here Jo," Alex offered. "Let me help you up...and over to the bed." Alex grabbed me by the waist and quickly got me into an upright position. I tried to stand up but found myself leaning on him because I couldn't trust my unsteady legs. He led me over to the bed where Mark had been getting situated. Mark was sitting on the edge of the bed when Alex surrendered me to him. He took me into his arms and gave me a slow, languid kiss. As he pulled me closer, he laid back on the bed, pulling me on top of him. As he continued to kiss me, I couldn't help but rub myself on top of him, letting my hands sneak up and play in his hair, while his hands caressed my legs and pulled them up until they were bent, one on each side. I felt him raise me up a little bit in order to slide his pants down to expose his erection. He settled me back down and I was able to feel his cock sliding through the crack of my rear. He stopped kissing me for a second. "Are you ready?"

"I am," and with no further words, he slid his penis into my stretched out rear-end. I was still able to feel him even though I'd been stretched farther than I ever though possible by Chantelle's hand. I placed my hands on his shoulders and levered myself up to a "riding" position. Mark put his hands on my hips as I got him settled comfortably in my rear. After a few up and down movements (and more than a few moans of pleasure from both of us), I indicated that I was ready to go for two.

"Well it's about time," Alex said. "Ya'll were acting like you didn't want to share." He crawled up on the bed behind me and gently pushed me back down on top of Mark. Mark was kind enough to grab both cheeks and part them so Alex could see what room he had to work with. The feel of his hands spreading me wide was...yummy. Still, I knew what was coming. I felt another pair of hands on my hips and knew that Alex was about to make his presence felt in a space that might or might not be able to accommodate him.

"Here we go," Alex said. And with that, I felt Alex's cock fighting to slide past Mark's. "I'm going to add a little more lube...just to make things easier." The coolness was welcome as I enjoyed the heat and friction from Mark's penis and tried to relax enough to let Alex join in. Slowly and steadily, Alex pushed his penis past my opening.

"Ohh..." I didn't have any words as I experienced double penetration for the first time. The feeling was unlike Chantelle's hand because it wasn't just the width that I was dealing with, it was the contradictory movements as the guy's cocks slid past each other and moved around in an effort to get settled. If Alex moved, I felt sensations on one side, but if Mark moved, then I felt sensations on the other. And if they moved together...I experienced sensory overload. I think my eyes might have been open, but I wasn't sure. If they were, then I'm pretty sure they were rolled back in my head like Maria's had been. I won't say that it didn't hurt, at least a little bit. But if this was pain, then I was ready to be a masochist. Alex and Mark continued to jockey for position for a little while, eliciting grunts and moans and squeals (those were mainly from me) from all parties involved. Finally, after a few minutes of pleasure, they settled down so we could proceed with the next step of the plan.

"Charlene, why don't you take your place up front?" Maria suggested. I tried to refocus my eyes as I watched Charlene make her way over to the head of our bed. "Alright Jo, time for you to complete the foursome." Maria seemed to enjoy her newfound role as director. "Charlene, lift up your dress so we can see Jo sucking your cock." Charlene didn't hesitate to comply with Maria's suggestions and I didn't want to disappoint any of them, so I opened my mouth to enjoy my second taste of Charlene.

Charlene stepped forward and slid her cock into my mouth while I moaned around the sensation. As soon as she got situated, the boys went to work. Alex and Mark started to pump in and out in and alternating fashion...never leaving me empty and leaving me confused about whether I was coming or going. Thankfully, with both of them holding my hips and waist, I didn't have to worry about which way I should be sliding. I was able to lose myself in the pleasure that they were generating inside my rear. I could tell that Charlene was enjoying watching me get fucked by the guys because she kept whispering "ohmigosh...Jo...that is so freaking sexy..." I responded by sucking with a little more insistency, occasionally switching up my technique and curling my tongue along the underside of her shaft as I tried to coax the cum out of her.

"Jeez that's a helluva shot," Maria whispered. "Did you get it Chantelle?"

"Mmm-hmm," Chantelle murmured as she licked her lips with anticipation. "I'm just waiting for the money shot now."

"Did you hear that Alex?" Mark asked. "The girls are ready to see it all." (funny...his breathing was just a tad ragged) "Shall we give it to them?"

"Heh," Alex chuckled, "I'm ready whenever you are. Charlene, are you ready?"

"Oh God yes," Charlene stammered. "Jo is GREAT at sucking cock."

"Will you look at that grin?" Chantelle asked. "I'd almost say that you like her better than me."

"No baby, that's not it," Charlene backpedaled. "You know I love how you do me, but I'd be lying if I didn't say that I really like Jo's technique."

"Fine, fine," Chantelle said with a smirk. "Are you ready? I think the guys are waiting on you."

"Yeah, if Jo keeps doing what she's doing, I'll be there in a minute," Charlene replied. Since that was all the encouragement I needed, I started going after Charlene's cum like it was the fountain of youth. I sucked with a little more force, tickling the underside of her shaft, moaning on her head, and trying every technique that I could imagine to send her over the edge. As my moans and my efforts got more enthusiastic, Alex and Mark started really taking advantage of their position. I could hear their grunts as they starting pumping in and out of my ass more aggressively, intermittently eliciting a squeal or delight from me as they hit spots I didn't even know could bring me pleasure. Seconds and minutes seemed to stretch into hours as I got lost on wave after wave of ecstasy...until...I felt Mark starting to tense up...then the first jet of cum filled my rear as Mark let out a grunt signaling the beginning of his release. As Mark continued to spurt cum into my rear, the activity spurred Alex's own climax and soon, both of them were shooting ropes of cum into my ass which was already filled to capacity. And to make sure that she wasn't left out, Charlene started to blow her load deep into my mouth and throat, quickly overwhelming my swallowing capacity. It didn't take long for the cum to start leaking out of my mouth and Chantelle made sure she got some shots of that. Then she quickly made her way around to get a close-up shot of Alex and Mark's cocks stuck in my ass with cum leaking from around them.

"Jo, I think you've got this little contest won. These shots are fantastic," Chantelle exclaimed.

I started to answer, but all that came out was "mmmpph...mmmm..." What I had been trying to say was "I can't wait to see them." But I knew I would have to try again after Charlene removed her penis from my mouth and I finished swallowing her gift to me.

The collective hard breathing from Mark and Alex started to slow down as they recovered from their orgasms, and Charlene reached down to stroke my face as she looked at the world through half-closed eyes and twitching in her own post-orgasmic glow. "God Jo...that was a great blow job."

Maria came up behind Charlene and started caressing her arms and chest. "Did you enjoy that hon?" Charlene nodded and I gave one final lick to her 'clit' as Maria pulled her from my space. I looked up into her face and saw her succumbing to Maria's ministrations.

"Were you enjoying yourself Jo," Chantelle asked. She'd come along side me and started to stroke my face even as Mark and Alex continued to lie there keeping me trapped in their sandwich.

"Honestly...I did. I wasn't sure that I'd be able to do it...but it was...intense," I replied through my own warmth and glow. "I think I...oooohhh." My thoughts were interrupted as Alex, than Mark, extricated himself from my derriere. Their abrupt exit left me feeling empty, and more than a little weak. Chantelle continued to caress my face as the guys moved me over onto the bed and started to clean themselves up.

"Jo," Chantelle started, "I do want to say thank you for helping us all out. I think that whatever Maria and Charlene and I get into is going to be interesting and you are MORE than welcome to join us whenever we're in the same area."

"Hmm...," I hummed out through the contented smile on my face. "Thanks girl. I know ya'll are going to have lots of fun together. We've got to keep in touch."

"Oh definitely," Chantelle said as she leaned down to give me a deep kiss...and lick off some of Charlene's cum that had dribbled down my chin. "You're amazing girl...and next time, I get to ride." She winked, gave a last caress to my face, then moved over to Charlene and Maria who were doing some caressing of their own.

Mark and Alex came back to help me up, bringing warm washcloths to help me clean my face and dab at some of the gifts they'd left behind in my behind.

"Oh...ok, as fun as that turned out to be," I squeaked out as I winced in discomfort, "I'm gonna be sore tomorrow." Alex chuckled as he ran a washcloth over and between my legs.

"We're gonna get you some fresh panties and clothes to wear before we take you back to Frank and Tom," Mark said. "And a pad," Alex chortled. I wanted to be mad at him, but I couldn't help but smile since I knew he was right. I was going to have to do something about the leaking I was doing, but I didn't feel like inserting anything else back there for awhile.

"Alright guys," Maria called out. "It's time for us to head home. You've had your fun...hell, we've all had a great time...but it's time for us to get to bed." She walked over and gave me a kiss that rivaled Chantelle's. "Thanks chica...you're magnificent. Don't be a stranger, okay?" Then she moved out the way so that Charlene could say her goodbyes.