The Bet Ch. 03

I felt his hands move under my ass and felt myself leave the ground as he lifted me more fully toward his mouth. His fingers moved between the cheeks and pulled me apart and I stiffened with apprehension. My nervousness put on hold when I felt his tongue trail its way down to the area between my cunt and my ass, and I groaned at the feeling, starting to tremble with the growing need of my body to find release.

His tongue trailed down even further to circle my asshole tickling me and I felt one finger join in the action. For a moment it was uncomfortable and I braced myself for pain, but there was none. Instead, a shot of desire echoed in my nerves and I found myself unexpectedly wanting more. I heard him moan as he eased the finger inside the tightness, my asshole flexing against his finger as it moved deeper. I felt my stomach turn somersaults in response to the excitement I was feeling.

From outside, voices cut through the fog in my brain reminding me of where we were, and I tried to quiet my responses, but the heat of Sean's tongue returned to my cunt and then slowly made its way up between the folds of my pussy to circle my clit. As a finger eased its way into the emptiness of my cunt, I started shaking, deep moans breaking from my mouth as I was immersed in the pleasure of feeling doubly filled and reckless with abandon.

I struggled to breathe. To catch a breath. To quiet the bucking and trembling of my body. But I couldn't. I let it take over. Oh God. I was racing the finish line. Shaking. Needing. Begging with words that came to me incomplete in their thought. Oh God, Please. More. Keep. Going. Don't. Stop. My hands grasped for anything they could hold on to. Twisting. Pulling. Then everything in my body ceased to exist. Suspended in that one moment where time stands still before all at once breaking free in wave after wave.

And wow....

I lay there spent, a puddle on the floor unable to move, yet wanting more of what had just happened. Sean lay on his side by me, his fingers caressing my bare skin waiting for me to rejoin him on planet Earth. His mouth occasionally sought some untouched place on my body to discover and taste.

This man was so incredible. I couldn't get enough of him. There was not enough of him. I wanted to open up my body and swallow him whole. To keep him with me for longer than tonight. For longer than the last few weeks. Sighing, I turned toward him, desperate to take whatever was offered and hold it close for as long as possible.

His mouth found mine and he kissed me gently before pulling away. "Ah, my little sex kitten, at last for your surprise."

He pulled away from me and grabbed a small brown paper bag that had been hidden beneath the blanket, opening it and dumping its contents on the ground between us. A white vibrator, about an inch and a half in diameter and six inches long, and a bottle of Eros lubricant fell out. I looked up at him questioningly, my eyebrows slightly raised.

Sean's face turned a light shade of pink and a sheepish smile played at his lips. "I uh..." He chuckled as his voice trailed off and he looked down at the ground away from me.

I laughed quietly at his sudden discomfort. It was such a switch from the confidence he seemed to exhibit seconds ago when he opened the bag. Considering how loud I had been just a few moments ago with a few thousand people outside, I should be the one that was suffering embarrassment. I looked at him again and smiled. "I uh... what?"

"Well, I've just always wanted to try anal sex. I was sort of... hopeful... you'd want to try it too." He looked back up at me from beneath lowered lashes and bit his lip for a moment before continuing. "You did seem to enjoy it..."

I turned onto my side to face him and quickly glanced down to where his jeans hid what I knew from previous weeks to be a very large cock. Oui Vey, I thought. I was actually considering it! I must be crazy, I mused. But then I looked at his face and my heart tugged. That feeling of desperation still strong. It was then that I realized that I did indeed want to give all of myself to him. I wanted to be his. The prize of my first virginity haven been given long ago, this final one could be forever my emotional link to him. Something special that only he and I could share and the one thing I could carry with me when it came time to say good-bye.

I looked at him and smiled. No attempts left to hide what I felt from him from showing in my eyes. "What's the vibrator for?" I asked, quietly.

He leaned over and kissed me gently, responding softly. "You'll see."

He stood and removed his clothes. I watched as each article of clothing fell to the ground and his beautiful body was revealed. As his underwear fell to the ground I looked up at his extraordinarily hard cock and felt that same breathless excitement that I had the first time I saw him naked, and, before I could think better of it, I was on my knees swallowing as much of his size as I could. My mouth watering and my tongue loving the taste of his pre-cum.

I heard him groan. "Roll over onto your stomach."

Easing off of his cock, I did as he asked, smiling up into his eyes before they disappeared behind me. As I was about to lie fully on the ground, his hands positioned themselves under my abdomen and urged my ass to tilt into the air.

I rested my forehead on the ground as his hands caressed my ass cheeks and massaged my lower back. I was tense and nervous and his gentle ministrations helped to ease part of it away, but my stomach was still knotted with trepidation. I took a deep breath and let it out slowly. Since there wasn't much I could do to help move things along, the wait was seriously playing with my psyche. Everything I had heard about anal sex included pain. And I wasn't big on pain. At all.

His hands continued massaging my lower back, his thumbs rubbing in circular patterns along my spine in a useless attempt to ease the tension away. Every moment spent not getting down to the business at hand, or rather business below, was making me an even bigger mass of nervous knots.

Suddenly, cold liquid hit my skin and I jumped and fell forward onto the ground taking him with me. Laughing, I looked back at him with surprise and was met with a mischievous grin. "Hey!" I exclaimed. "That wasn't very nice." I pouted, feeling better now that the tension was somewhat broken.

"Just wanted to make sure you were still awake over there." He quipped. "Actually, I didn't realize it would be that cold." Moving off of me, he reached out to help me into a sitting position, and then put his hands on my shoulders. I felt his fingers gently travel down my arms, and his hazel eyes looked into mine, concern written on his features. "You really seemed to have drifted away for a minute there. Is everything okay?"

"Just... nervous, I think." I responded quietly.

"Changing your mind? That'd be okay, you know."

I self-consciously chuckled. "No, I'm not. I'm just... nervous." I let another giggle escape and confessed. "The wait is killing me!"

Sean laughed in response and as his lips lowered towards mine he whispered "Good, because I would hate to think my research on this ass fucking business had been wasted. That was a lot of damn book reading there!"

Choking on surprised, nervous laughter, I whispered in return, my lips resting on his, "Well, then, let's get this show on the road!"

He chuckled and after a very brief kiss, moved back into position behind me. I felt his hands once again massage the taunt skin of my ass cheeks. This time though, there seemed to be an added desperation to his movements, as though knowing that I was unable to wait had keyed his desire. As he moved closer to me, I could feel his hard cock brush between my legs occasionally hitting my pussy, teasing me.

I heard him pick up the bottle of lubricant and braced myself for more cold liquid, but was instead met with warmth and realized that he had somehow managed to warm the bottle. The liquid trickled down my ass crack tickling me, but his hands started their motion once again, this time moving closer and closer to the small opening before pulling away.

At the loss of his hands, I felt cold, but a jolt of excitement shot through my nerves as a soft buzzing sounded in the background. Sean turned the vibrator on lightly trailing it over the inside of my thighs and over my pussy lips.

I could feel my body come alive and ready itself for him once more. My arms trembled as they held my weight. Sean knew how to tease me and he was doing a good job. Touching everything but the area that he knew would send me soaring. I felt the plastic device brush over my cunt and moved myself closer to it hoping he would take the hint and slide it inside to play around. He did not disappoint. Smooth plastic stretched the walls of my cunt apart, and it slid in and out with ease. Every so often it brushed the top wall of my hole, nicking my G-spot. Before long, I was moaning and ready to cum.

I felt his fingers on my ass and his fingertips creep toward my asshole, but in the position I was in and as turned on as I now was, I felt no trepidation. I only felt a desire to be filled once again so that I could cum and spasm around him.

The vibrator left my cunt and trailed upward toward my raised ass and buzzed around the opening. I tightened in reflex, but soon relaxed as it eased slowly inside of me. Sean moved closer to my pussy and I felt his cock brush against the soft skin there and I moaned as the tip of him brushed close to my engorged clit.

He eased the vibrator back a tiny bit until only the tip was inside of my ass, and I felt the tip of his cock position itself outside of my cunt, brushing over the wetness before finally easing inside.

"God, I never get tired of how that feels. You are so tight and wet... and hot." He let out a pent up breath of air and moved back and forth for only the briefest of times before pulling out. The vibrator being pulled back and away from my body as well, I was suddenly alone.

Whimpering, I tried to seek him out with my pussy, but I couldn't find him. Turning my head to look behind me, I watched as he poured lube onto his hands and massaged it over his cock over and over as if masturbating. I looked at his face, taught with restraint and felt a thrill of power at the knowledge that I could make him feel this good, want me this much.

I decided to join him for a moment and moved my right hand down to toy with my pussy and massage my clit, wanting so much to ease away the tension and orgasm, but instead I waited, and soon he was behind me. Once again, he brought the vibrator up between my thighs and rubbed it over the outer lips of my pussy, just missing my clit. I wiggled my hips trying to bring that magic wand to the place I needed it to be, but he was one step ahead of me. Moving it before I could make contact.

I felt the tip of his cock at my asshole and knew that it was time to lose my last virginity. Once again, I braced for pain and felt it only slightly as he eased himself inside of my well-lubricated asshole. I gasped at the unexpected pleasure of being so filled. Complete.

He moved slowly back and forth, his breathing ragged, and I felt the tension in his body as he held himself just out of reach of full release. He moved the vibrator over my pussy, pushing me toward orgasm, but always missing the crucial spot.

I heard him growl and knew he was losing his control, ready to cum. "Damn it! I can't...wait" He gasped for breath. "Cum... Oh God, please...Cum with me. Now."

I felt him start to shake behind me and groaned in frustration at the wandering, misplaced vibrator. Holding myself up with one hand, I reached down and found his hand, slamming the vibrator against my clit and holding it there.

It only took seconds for my body to respond to the sensations and drive full force toward release. I trembled and moaned as every nerve ending and thought focused on my ass and pussy. Like a force that sucks energy from everything around it I could feel all the tension in my body gather and gain strength deep inside of me. Red-hot fire shot its way down my arms and legs and coursed through my body and then suddenly I was there. Electricity shot through my veins. Shaking, I felt the muscles in my pussy and ass tighten around him and then start quaking as the orgasm that kept eluding me finally shook through my body. Wave after wave of pleasure consumed me and I bucked against him. Squealing, I tightened once last time and felt Sean pull out of my body. Warm liquid followed as he came in spurts down my ass and all over my back. He collapsed against me sending us both crashing to the floor.

We lay like that, him on top of me, for a few minutes each trying to catch our breath. Slowly awareness of our surroundings hit us at about the same time. Cheers sounded through the walls of the booth, and we turned to grin at each other as he eased himself off of me.

"Do you think they're cheering for us?" I asked with a giggle.

"Probably. You were moaning and groaning pretty loudly."

I laughed softly and blushed, at a loss for words. "Well..." I felt, more than saw, him smile as he lay on the blanket beside me.

"I liked my surprise."

"I'm glad. I enjoyed it too."

I laughed at that. "Even though it apparently took a lot of 'damn book reading'?" I paused, looking for a way to ask the next question. "I am wondering, however. Now that you've tried IT and enjoyed IT," unable to bring myself to actually say the words ass-fucking out loud "do you plan to do it again?... With me, I mean?" " I looked up, caught him blush, and smiled to myself, amazed that after all we'd shared he could still feel embarrassed.

That last thought stuck in my brain, "all we'd shared". Not waiting for an answer to my previous question I rolled onto my side and looked at him. "I've had fun. Not just now, but... this whole thing. The betting. You." I looked at him searchingly trying to keep the hope out of my voice that this could turn into a long-term relationship. "Anyway, I was just wondering... what now? What does tomorrow bring?"

"Well, I don't quite know. I think that really depends upon you."

He rolled away from me and reached for his jeans. Feeling a fleeting disappointment that he hadn't really answered the question, I looked away, but turned back toward him as he rolled back toward me and laid down next to me holding out a piece of paper.

"What's this?"

"Open it."

I did as requested and unfolded the paper. Typed out were sixteen names I'd never seen before, and I looked at him. "I don't understand."

"Well, now that football's over, I had to find something else for us. Those are the names of sixteen college basketball teams. After that, I figure there's baseball, soccer, and if we get desperate, lacrosse." He smiled, his eyes lighting up. "Would you care to make a wager?"

I smiled, remembering our first discussion. "Well... it'd have to be something sexual."

Sean reached forward and put it arms around me, pulling me toward him for a kiss. "Absolutely."