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The Challenge

Category: Anal Sex
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Chicago. The Windy City. I tried to look out the windows of my hotel room to calm my nerves but I was unfocused and flighty. The scenic lake in the distance couldn’t hold my attention for more than a few seconds at a time.

Panic seized me. Again.

During the past hour my nervousness had escalated from apprehension to something bordering on terror.

I took deep breaths to calm myself but my pounding heartbeat seemed to double its rate in my chest. Pacing, I tried to work off some of my anxiety but the only thing that could soothe me now was the knock on the door that would either be my salvation or my downfall.

* * *

An offhand comment two years ago had led to this moment.

I have struggled with my weight my entire life. When my size crept toward morbid obesity, I realized that getting a grip on my food addiction was the only way to avoid an early death. But I felt powerless to do anything about it. I’d never had the resolve or will-power to diet for more than a month at a time. You would think that something as simple as putting food in your mouth would not be so difficult to control. But I couldn’t fight it, and I knew if I didn’t somehow overcome it, I would die by my own hand.

What I needed was an incentive. A goal to work toward. The idea of losing weight is not a very big motivator; you can’t just picture yourself as thin and confident and suddenly be in that place, ready and willing to change your entire lifestyle for a fleeting prize. If it were that easy, we’d all be thin. Skinny as supermodels. No, I needed something bigger than that to inspire me.

Sex as a motivator? Well, why not? It feels good and can give pleasure even more satisfying than food. I have two sexual fixations. Gay men and anal sex. I’m not sure why I’m so fascinated by gay men. Maybe human nature simply wants what it cannot have. They are unattainable to me. As a woman, I could never be a part of what two men can share with each other. Maybe my anal fixation stems from that absorption. Or maybe from the fact that it looked like I would never experience it.

My husband flat-out refuses to have anything to do with anal sex. He is a scientist and is really weird about germs and bacteria. He won’t go there even with a condom. He won’t talk about it much but he’s said enough that I know it will never happen. And no amount of begging will ever change his mind.

* * *

When my health concerns arose, I had just made the acquaintance of a sweet young gay man over the internet. Andrew. He had answered all my questions about anal sex frankly and honestly, and probably laughing to himself behind his computer screen at my ignorance and obsession. At least he never laughed at me openly. He even directed me to some written literature on the subject that he thought might inspire my husband. Not that it helped, but I found it interesting so at least his efforts weren’t for nothing.

One evening I found myself chatting with him about my deepest darkest secret. My weight. I think it was easier for me to talk to him about it because he couldn’t see me. I didn’t have to look in his eyes to see if he was judging me because of my size. I was griping and complaining to him, explaining that losing weight was something I had to do or I was going to die. I honestly felt that way at the time. Every bite of food I put in my mouth was like a death sentence.

“I feel helpless,” I moaned. Well, he couldn’t hear the moan but it was there. “I’m fat. I’m ugly. I can’t do this. I can’t control myself.”

“Good Lord, girl, calm down,” he wrote. “If this is something you really want, then you can do it. You will do it. You just need something to motivate you.”

Nothing came to mind. What could possibly motivate me to lose nearly half my body weight? But he knew me so well already. Even after only a month of corresponding via e-mail and chat, he had quickly formed an idea.

“In two years, if you lose the weight, I’ll fuck you in the ass,” he wrote.

Holy shit, that was not what I expected. “Uh, what was that?” I asked, although it was clear for me to read in the messenger box.

“You heard me, I’ll give you what your husband won’t.”

It took about ten seconds for every possible consequence to run through my mind. My husband. I’m not a cheater; I’m not looking for an affair or a way out of my marriage. And he’s gay, I reminded myself, and he has a partner. This wouldn’t be an affair though. Just something to satisfy my curiosity. But he’s gay, I reminded myself again, shaking my head. Why on earth would he offer to do that?

“Are you drunk?” I wrote.

“No more than usual,” he replied. I could almost see his grin.

“But you’re gay,” I wrote, not knowing what else to say, not sure where this was headed, not sure I wanted to know.

I could almost here him laugh as he wrote back, “So? What’s that got to do with anything?”

“What about Jeff?” I asked, referring to his partner.

“He won’t mind. He’ll think it’s funny, actually.”

Could I have sex with a stranger? I mean, I really didn’t know him that well. You will in two years though, someone said in the back of my head.

I never said yes and I never said no, but from that day forward things changed between us. He became the unofficial coach of my diet. I guess he needed a project. As if he weren’t busy enough already. He constantly both pestered and encouraged me, and believe me, he was a real asshole at times. But it worked for me. I started seeing some results. My energy came back with every pound that I lost. I found myself exercising and being able to tolerate the exertion. I was finally able to control those cravings that I had been a slave to for all those years.

I realized it wasn’t so much an incentive that I needed as just someone to be supportive and share in my day-to-day struggle. Someone who would push me but who would also understand when I lost a battle with my willpower and who wouldn’t judge me too harshly for it.

My husband certainly wasn’t around enough to help me. His research demanded such strange hours that I was lucky he was home long enough to notice me. But I reminded myself that’s what I’d found so attractive about him in the first place. The work he did held such potential; his lab had already made several breakthroughs that would benefit many people. I’d always known in the back of my mind that I would never be higher than second place with him. I loved him and could live with that. But I couldn’t help being restless at times.

* * *

During those two years I kept Andrew’s promise in the back of my mind, not really thinking it would ever happen. Not that I didn’t have some wild fantasies about it. I really wanted to experience anal and who better to do it with than a gay guy. If they can’t get it right then there is no hope for the rest of us.

I was resolved not to bring it up again. But as the last few pounds melted away and I reached my ideal body weight of 110 pounds on my five-foot frame, he typed one evening, “Well, it’s just about time, isn’t it?”

“Time for what?” I asked as my palms turned sweaty and my heart rate quickened.

“You know,” he wrote. “Do I have to spell it out for you?”

“Maybe…” I couldn’t take the first step. He would have to do that.

“You kept your end of the bargain and now it’s time for me to keep mine. Whether we go through with this or not is up to you. Just name the time and the place and I’ll be there. Or we can never mention it again.”

* * *

Which brings me back to Chicago. The Raphael Hotel. Fifteenth floor, corner suite, gorgeous view of Lake Michigan right out the window. I paced, ignoring the view, thinking over and over that he’d be here any minute.

Nervously I checked the mirror for the fifteenth time. I never looked at myself anymore. I couldn’t get over the difference. Who was that looking back at me? I’d been so fat for so long that I barely recognized her. She smiled at me. I couldn’t wait for Andrew to see me. He’d seen the before pictures. Now he could see the after. He could see what he’d done for me, how he’d changed my life.

I finally heard a knock on the door. No turning back now. I took one last deep breath and somehow managed to walk to the door.

The man who greeted me in the doorway was not what I expected. Actually, I’m not sure what I was expecting. I had only seen one grainy black-and-white photo of him taken several years before. It looked nothing like him. His ash blond hair was cut short and spiky and his beard was gone showing off a straight jaw and high cheekbones. His nose was a little crooked but I didn’t think it was too big like he always complained.

He stood slouched against the doorframe, grinning a crooked grin, hands in his pockets.

“Hi, Andrew,” I said shyly, looking up at him.

“Hello, Jessica,” he said, his voice rich and smooth like fine whisky. It was the first time I had ever heard it. In those first few seconds I saw in his eyes everything I needed to know about him. They were brilliant clear blue and in them I could see gentleness and kindness. I could trust this man, he wouldn’t hurt me.

I stepped backward, silently inviting him in.

“I wasn’t sure you’d come,” I blurted after a moment. “I was scared that you wouldn’t and scared that you would.” I don’t know what made me say that.

He laughed then, helping ease some of the tension that I felt. “What do you think now that I’m really here?”

“I’m not sure. I’m still scared.”

His blue eyes held me as he quietly said, “You have nothing to fear from me, Jessica. You know that, don’t you?”

I nodded. I could hear the sincerity in his voice, see it in those incredible eyes.

After a moment he moved to circle me, looking me up and down, appraising me. “Darling, you look fantastic. How much weight did you lose?”

“Eighty-five pounds. Can you believe the difference?”

Shaking his head, he said, “Wow. I can’t get over it. You really do look wonderful, babe.”

I smiled then, happy to meet with his approval. After all, I had done this almost as much for him as for myself. His friendship meant a lot to me. I wanted him to be as proud of my new body as I was since he’d played such a large role in reshaping me.

“You were a good coach, I couldn’t have done this without you.”

He brushed that aside. “You always had it in you, you just needed a push. Several of them. But I’m a master at that,” he winked.

He moved toward one of the armchairs. “Do you want to just sit and talk for awhile? We’ve never done that. Well, not in person anyway.”

Relieved, I sank onto the chair opposite him. I was finally relaxing. He put me at ease right from the beginning.

We could have talked for hours. About our families, our friends, our pasts. But I could tell he didn’t like being cooped up in this room. It wasn’t long before he was walking around looking out the windows. The lake was a beautiful blue backdrop for the sailboats that skimmed its surface. I admired the way he moved, his body slim and graceful.

“Do you want to go out?” he asked suddenly. “We could get something to eat.”

“I don’t think I could eat a thing, if you can believe that!” I laughed. “But we could go to Blue Chicago and get a beer and listen to some jazz. It’s less than a mile from here.”

“Why not? But you know me and beer. Cut me off after two.”

I looked at him doubtfully, “Well, I can try, but I’m not sure you’ll listen.”

* * *

We stepped out into a muggy Chicago evening and called our greetings to Vince the valet. The walk wasn’t that far but we were sweating after just a couple of blocks.

The bar, when we found it, wasn’t that crowded yet. Too early for all the regulars. We mellowed over a couple of beers and the blues and before I knew it I was leaning into him in a familiar way I hadn’t done with anyone in years except my husband. He was just so comfortable to be with. We were old friends after all, even though we’d just met in person hours before.

He smelled delicious. I wasn’t sure what he was wearing, but I couldn’t get enough of it. Maybe it was just him, his natural scent. I know I shouldn’t have but I found myself envying Jeff, his lover of six years. Maybe there was more emotion in this for me than I’d thought. I looked up into his eyes and smiled. He leaned toward me and breathed in my ear, “You wanna get out of here? All this smoke is making my head hurt.” That caress of his breath sent shivers all through me even though what he’d said wasn’t the least bit seductive.

I nodded, not trusting myself to speak. Just his nearness was causing me to get damp. We opted to take a taxi back to the hotel. Our fingers interlaced in the backseat of our cab as if it were the most natural thing in the world. He had beautiful hands. Strong with long tapered fingers. They looked capable of either chopping firewood or sketching a landscape. In no time we were back at our hotel, Vince opening the door for us. As we boarded the elevator, I began to tense up again. I could actually feel my muscles tightening. Andrew sensed it and put his arm around my shoulders.

“Hey, girlie, calm down. You look like you’re going to have a stroke,” he said squeezing my arm. “We still don’t have to do anything, you know. You’re in charge of this. Whatever you want to do is cool.”

I tried to smile back at him. What was he really thinking? I know he didn’t come all this way just to get laid, but I wondered if he would be disappointed if he didn’t. No, he wasn’t like that I told myself. He would be happy with whatever I was willing to give and not think twice about it. Funny, this was supposed to be the culmination of all my fantasies and the prize for which I had worked so hard. I figured it would be me having to talk him into going through with it.

When we got back to our suite, we stood at the window in the darkness looking at the lights. There were still a few boats left on the lake, their multi-colored running lights twinkling in the distance. The lights of the city spread out to our left, the bustle of the Chicago nightlife swirled below us.

“Bubble bath,” he suddenly spoke.

“What?” I said, jumping a bit at the sound of his voice.

“Bubble bath,” he repeated. “Let’s get in the tub and relax.”

I could barely see him in the darkness, but I knew suddenly that I wanted this. Every feeling he could give me. I wanted to experience it all.

“Ok,” I nodded. I reached out tentatively and stroked the clean line of his jaw. His lips came down and brushed mine briefly, fleetingly before he headed into the bathroom.

I heard the water running after a minute. I kicked off my shoes and followed him.

“There isn’t any bubble bath,” he said, “we’ll have to make do with this.” He held up the orange-scented shower gel the hotel provided.

“Smells good,” I said. Now I was feeling a little shy, thinking about undressing in front of him. He tugged his shirt out of his jeans and pulled it off over his head. My fingers reached out unconsciously to stroke the tattoo on his right arm. Sea turtles and a jellyfish.

“Nice,” I said, meaning more than the tattoo. His skin was tan and smooth, his body lean but not too muscular. A light sprinkling of blond hair covered his chest and trailed down his smooth stomach before disappearing into the waist of his jeans.

“Thanks,” he smiled. “Your turn.”

I hesitated but then started unbuttoning my shirt. He was already pushing down his jeans. He reached behind me and turned off the light. “Maybe that will help, if you’re gonna be shy about it.” The lamp from the bedroom filtered in slightly, providing a soft warm glow in the darkness. I could still see him grinning at me.

He quickly slid out of his boxers and lowered himself into the tub. He offered me his hand as I finished undressing and I slid in across from him.

Ok, that wasn’t so bad, I thought to myself. After all I had worked awfully hard to get my body looking this good. I just figured it would be wasted on him. Eyes closed, I let the warm soapy water wash over me and ease my tension. I sighed out loud as he took one of my feet in his hands and began massaging it.

“What size are your feet?” he laughed. “They’re smaller than my hands.”

Not exactly terms of endearment, but I couldn’t help laughing along with him. He always knew what to say to make me laugh and put me at ease. “Size five,” I answered.

“Good Lord, how do they hold you up?” he joked. He smiled at me and then held out his arm, inviting me closer. “Come over here.”

I scooted around so I was lying against his chest, the bubbles reaching almost to my shoulders. I think I sighed again as his arms encircled me, holding me tightly. He didn’t speak but the rhythmical rising and falling of his chest was hypnotic. I felt the tension drain away as that simple regular motion soothed my nerves.

I don’t know how long we sat like that, but after awhile he began lightly nibbling on my neck and ears. I melted completely, putty in his hands. Every cliché I had ever heard about this moment rushed through me. I never let anyone near my ears, not even my husband. But I let go and surrendered to him. Total trust. Absolute faith.

His fingers began kneading my neck and shoulders, although I don’t think I could have relaxed much more. “Wanna go to bed?” he asked. Just like in the bar, his breath on my skin sent shivers down my spine. I didn’t hesitate. The time for hesitation had passed. We stood in unison and quickly rinsed off the bubbles, reaching for towels as the bath water drained beneath us. In the muted light, we drank in the sight of each other, naked and no longer shy. I dried him and wondered over each scar I found as well as the second tattoo on his left shoulder blade.

I shamelessly tasted them all, relishing the flavor of his skin, enjoying how he felt under my tongue. My fingers traced the muscles of his back, exploring him hesitantly at first, but then more boldly as he held me, letting me explore every part of him. When I looked up at him he smiled his approval.

I felt a growing heat within me that spread downward. I wanted him to touch me, I wanted him to fill me. He was aroused, his cock hard and pulsing against his stomach, and I felt a sense of pride that I had made him that way. I reached down to stroke him, his skin velvety soft yet hard at the same time. As I lowered my head to taste him there, he stopped me. I looked up questioningly into his eyes. Had I done something wrong?

His shook his head slightly and said, “This isn’t about me.”

Oh, but I wanted it to be about him. To make him feel what I was feeling. Somehow, for whatever reason, the purpose for this rendezvous was becoming distorted in my mind. He drew me up against him and kissed me. Deeply, passionately. Unexpectedly.

I don’t remember walking to the bedroom, but suddenly we fell onto the bed, my mouth searching his like someone possessed. I knew I would want him, but I didn’t expect his passion to meet mine. I still thought that, for him, this would be just a duty. Something he did because he promised. He was gay…he couldn’t really want me could he? But he surprised me. His tongue sparred with mine in those initial frantic kisses, stirring something in me that was almost frightening in its intensity.

So many nights over the past two years I had sat at my computer and been touched by his words. But it paled in comparison to the touch of his skin against mine, his hands on me, claiming me.

My hands tangled in his hair drawing him even closer. He responded by moving away from my mouth and down my neck where he stopped to lick and bite the sensitive skin. Not hard enough to leave a mark, but hard enough to make the hair stand up on the back of my neck. Slowly he kissed a trail down to my breasts. His lips caught one of my nipples, encircling it, his tongue lashing at it. I moaned, my body arching up into him, lightning racing through me. He knew I liked it rough, that much I had shared with him in the past two years. His fingers found my other nipple, pinching it tightly and twisting it, my body writhing beneath him. The pleasure he gave me, between his insistent fingers and the rasping of his teeth, brought me quickly to the edge. I was in heaven. Beyond heaven. I would have orgasmed if he’d kept it up much longer.

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.


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