The Challenge

But he moved then, down down even further, his tongue dipping into my navel, teasing me. He looked up at me and grinned a sadistic little grin showing me how much he enjoyed tormenting me.

My juices were overflowing, soaking the sheets beneath us. His lips continued downward, his hands spreading my legs. At the first unexpected touch of his mouth against my clit, sucking and nibbling, I exploded into bliss. Electricity flashed across every cell in my body. I tingled from head to foot as he continued to gently pull at my clit with his mouth, drenching his face with the force of my orgasm.

"Oh God, stop, Andrew." I begged for mercy after a moment, pulling on his hair. I was weak and trembling, my flesh too sensitive to endure much more.

That same devilish grin returned as he pushed my knees up toward my chest. I felt his tongue lapping at the juices still gushing from me . He traveled further down again, finally licking around my anus. This was the reason I was here I reminded myself through the fog in my head. His tongue moved lazily in slow circles around my puckered hole, stopping at times to push in gently. I moaned at the slightly kinky and unfamiliar pleasure of it. I needed more…more… I thrashed restlessly on the bed, trying to get more of him.

"Relax," he ordered. "Bear down and let me in."

After that orgasm, if I relaxed any more I might slip into a coma. But I did as he asked, trying to relax that ring of muscle that separated us. Trying to open for him. The last barrier between us dissolving.

His tongue became more demanding then, spearing me, driving in and out of me. I felt two of his fingers enter my sopping pussy, stroking deeply. I had never had multiple orgasms before but this dual stimulation was moving me toward something I had never experienced. But suddenly his fingers withdrew from me and before I could mourn the feeling of emptiness, a fingertip slipped inside my ass. He went slowly, working that first finger in gradually so that I felt no pain. Only a slight burning that excited me even more once I realized how good it felt. He went back to licking my clit at intervals while his finger moved in my ass. I was so distracted by the pleasure he was giving me that I barely felt the second finger join the first. He paused then, letting me get used to that feeling of fullness.

My juices were still flowing downward, coating the fingers that impaled me, allowing him to move easily within me. He drove deeper and faster, my anal passage burning and tingling from these new sensations. My hands fisted the bed linens beneath me as I gasped and moaned in delight. He smiled up at me, pleased with his efforts. When the third finger entered me, I knew I was on the edge of something incredible. There was no pain as I had feared, only an overwhelming sense of fullness and completeness. The burning was gone and I felt only a longing to be filled even more, as much as he could give me.

After a moment he got up and I felt suddenly empty and alone. He was back in an instant with a tube of Astroglide and a condom. I watched as he rolled the condom over his cock and began to stroke the lubricant over the head and up and down the shaft. Watching him touch himself was incredibly erotic. My mind was trying to comprehend that cock moving inside me when he said, "Turn over. It will make it easier for your first time."

I obeyed him, submitting to his every command. I'd imagined looking up into his blue eyes as he took me, but he was the expert after all. He positioned a pillow under my hips to better angle his penetration.

As he spread my asscheeks with his hands he spoke again. "Are you sure? Are you ready for me?" At all times, he was giving me the chance to back out. I loved him for that but I wasn't about to change my mind now.

I nodded and simply said, "Yes."

I closed my eyes as he placed his cock at my entrance. I relaxed as best I could and felt him slowly begin to push forward.Let go, trust him. A thousand thoughts entered my mind as I opened myself to him, exposing my greatest desire and fear. But he drove all thought from me as the thick head of his cock moved slowly into my tight entrance. There was pain, for just a moment, but it soon faded into a dull burn. I was stretched – so wide it was almost too intense and I gasped. He stopped, allowing my body to adjust to the feel of him.

"Stop me if it hurts, ok?" His arms came down on either side of me as he held himself above me. I could see the strength and power of his forearms, the muscles straining. "Remember how I told you to bear down on me and don't tense up…"

"I'm ok," I answered, pushing back against him slightly to show him I was ready to continue. The burning was still there, but I didn't want him to stop. It wasn't painful anymore – in fact, the tingling radiated deep through me, turning to a pleasure I'd never known before.

Little by little he eased himself deeper into me, sinking into my depths, taking a path no one had ever traveled before. I'd never felt so completely possessed. I loved the feeling of him owning me. I gave myself to him totally, even if just for this moment.

He would not have agreed with me, but I felt I owed him this. Everything he had done for me in the past two years; he alone was the one who deserved to take this virginity from me. The fact that my own husband had refused had made it that much easier for me to save it for him. For him alone. I would never have dreamed of doing this with anyone else.

The slow, agonizingly sensual journey finally ended as I felt his pubic hair brushing the crack of my ass. He just froze there, not moving a muscle, still balanced above me. I reached back for him, trying to draw him down on top of me but he hesitated.

"Lie down on me," I begged him. "I want to feel all of you."

Still hesitating, he lowered himself until his chest was covering my back and his cheek was resting against mine over my shoulder.

I knew he couldn't stand the feeling of being weighed down, and I knew what it must cost him to feel like he was forcing it upon me in spite of me asking for it. But I reveled in the feel of him. His weight was heavy upon me, pressing me, covering me. It made me feel safe, protected, sheltered. Owned. I was the one who brought security and stability to my relationships and I gloried in being able to let go completely, allowing him to take that burden from me. If only for one night.

The long length of him buried inside my ass, where no one had ever been before, only added to that feeling of complete surrender. Slowly he moved his hips in a tight motion, grinding his pelvis into me. He took longer, deeper strokes as my breathing quickened and I began moaning into the pillow. I turned my face toward him and we shared a short awkward kiss over my shoulder. The sensations that bubbled inside me were so overwhelming I almost felt hysterical – why had I never done this before? Yes, yes, so good…

My body took over and began pounding back into him, matching his strokes and demanding more, wanting it harder, faster. His hands moved under me and he began rolling my nipples between his fingers, pulling at them and squeezing them roughly.

"Oh God," I moaned, as his tongue teased my ear, trembling as his breath caressed that sensitive skin. He could feel me tensing beneath him, nearing orgasm. I tried to hold back, to delay it. I desperately held on to the pleasure building inside me, wanting it to last just a little longer. Agonizing seconds passed as my body and mind waged war, struggling between control and release.

At that moment one of his hands slid down my front and burrowed between my pelvis and the pillow searching for my clit. When he found it, he pinched it once between his index finger and thumb and I lost it. My entire body exploded in one huge firework. Every nerve-ending electrified, every square millimeter of my flesh stimulated beyond even my wildest fantasies. I felt his cock growing inside me, pulsating then jerking as he orgasmed with me.

I don't know if I screamed. I may have blacked out for second. I don't remember anything but the feeling of the most intense orgasm I have ever experienced in my life. Overpowering, almost unbearable sensations crashed through me.

When I regained my senses, he had rolled off me, pulled off the used condom, and pitched it toward the trash can. I was shaking uncontrollably as he rolled back beside me and gathered me in his arms. I clung to him as our breathing returned to normal and the sweat on our bodies dissipated.

He cupped my face in one big hand and tilted my chin up so I would look at him.

"You ok?" he asked, his brow furrowed with concern but half-grinning as he said it.

"That was…" I was the kind of person who was never at a loss for words, but for once in my life I couldn't finish a sentence. All I could do was grin this big dopey, contented grin.

"I know. It's intense the first time, isn't it?" He kissed me gently on the forehead and said, "You had me worried there for a second."

"I think I may have passed out there for a minute," I giggled. The hysteria was catching up to me. "Wow. Let's do that again."

He just shook his head with a big smile on his face and said, "You're so funny. I don't think you can take it again right now, and I know I can't." He laughed, "Besides, I'm starving. Feed me."

We decided not to go out again and ordered a deep-dish pizza from Giordano's. We had a disagreement over the toppings but finally decided on sausage, pepperoni, and fresh tomatoes. And not that I needed a treat after what we'd just done, but I couldn't resist an order of tiramisu. It would take a little over an hour to be delivered so while he went out to find us some more beer and get some ice, I jumped in the shower.

As I washed the sweaty film from my body, I couldn't help exploring. My ass was pretty sore. There was no way I could do that again anytime soon. But that soreness felt so good. I smiled, thinking how glad I was I had done this.

I was a little disappointed that he didn't join me in the shower but I realized this was just a one-night thing for him and not some budding romance. All I had to do now was feed him, put him on a plane in the morning and his obligation would be over. I just hoped I could put this night in my memories as easily as he could.

He already knew I was halfway in love with him. I had told him as much not long after we met. But he's gay, I always reminded myself, safe because even if I wanted him it could never happen. Now that I knew him intimately, I hoped I could return to my husband and put this obsession behind me. Or at least be content with what I had waiting at home. I wasn't so sure that would be possible.

We spent the rest of the evening eating and talking and listening to music. The pizza was fantastic, deep-dish Chicago pizza, two inches thick, with the cheese just dripping off it.

"I can't eat another bite," I said, after about a slice and a half. "Can you believe it?"

"I'm proud of you, Jessica. You've really changed things around, haven't you?" He grinned.

"Yeah, and I feel so much better now. I like myself a lot better, too. I don't feel like I have to hide anymore. I don't worry what people are thinking or saying about me behind my back."

"You shouldn't worry about other people anyway," he said. "You were always the same person inside and if people couldn't see that, then it's their loss they never got to know you. Fuck ‘em, that's my motto," he said with a smile.

"You're a sweetie," I said. "Do you want some of this tiramisu? I can only eat a couple of bites, but it's really good. I'd hate to waste it."

He shook his head, making a face. "Don't think it would go with the beer," he said, raising his bottle.

We didn't talk about what we had shared until we were so tired we knew it was time to go to bed. As we lay side by side under the covers, I summoned my courage and asked him if it had been good for him, too.

"Of course, silly goose," he answered, turning toward me and laughing. "I don't dislike sex with women, you know, I just prefer men. It's been a long time since I was with a woman," he mused, "Over ten years ago."

"Well I'm glad I wasn't a complete turn-off for you," I countered, giggling with him.

"No, dear, you were anything but that. As a matter of fact…" He took my hand and placed it on his cock, which was about half-hard. It twitched at my touch.

I laughed out loud at him then but began lightly stroking him through his boxers with my fingertips. His cock responded and got fully hard, thick and ready. He shuddered as my hand encircled him.

"I may be getting old but I'm not dead yet," he said.

"Oh, yeah, you're so old at thirty-two, Methuselah," I couldn't resist teasing him. He often made silly little comments about his advancing age.

My hand reached into the waistband of his boxers to feel the silky skin of his erection. This time he didn't stop me as my lips lowered to taste of him.

The next hour we spent leisurely making love. We both knew this might be the first and last time we ever met in person. Without any hesitation he spread himself to me and let me explore him the way my husband never would. Twining my first two fingers together, I dabbed on some lube and slid them up his tight ass. Curiously I wiggled them and watched his eyes roll back in pleasure. It was so smooth… slick but not wet. When his muscles rippled around my fingers, accepting me, I understood the fascination with this forbidden passage. Gently he showed me where to find his prostate… watching his eyes as I stroked it was thrilling, knowing I could be inside him and bring him such pleasure. It saddened me that my husband would never know it, but I wasn't thinking of him now. When Andrew and I finally did sleep, we snuggled together, satisfied and content.

* * *

The next morning I put him in a cab headed toward O'Hare. I was going to stay on a few more days to meet my sister for a long weekend of shopping. A celebration of my new body. I had planned it this way so I wouldn't have to rush right home. I needed time to digest what I had done.

I don't know what last night had meant to him, if anything, but for me it was more the solidification of our friendship than the promised payoff of a challenge. That he had been willing to give of himself like he did made him even more special to me, if that were possible.

What we shared would always hold a special place in my heart. I just hoped the memories would be enough to sustain me when I went back to my boring, unimaginative life.

As I greeted Ann later in the day, my mind was already racing ahead to the day I returned home, wondering what I would find in my inbox.

THE END