Lady Fortune's Smile

"I'm sorry I was such an ass." I sigh. I hear him sigh as well as I walk with him to his bedroom. Along the way, I shed my soaking wet work shirt, leaving it on the floor somewhere carelessly.

"It's okay, you were trying to protect me." He sits down on his bed after kicking off his underwear. I try my best not to look down. He pulls me down onto the bed beside him and wraps his arms around me, tucking his head into the crook of my neck.

"Hmm. That's right, but from the looks of things, you can take care of yourself." I chuckle, trying to lighten the mood. "Remind me never to piss you off." He giggles and moans a bit as I soothingly rub his back.

"Tell me honestly, Theo…do I really come off as such a cheap slut? Is that why I keep attracting the sleaziest guys?" He stares off into space, nuzzling closer into me. I force myself to concentrate on next week's ballgame to keep my erection from growing too noticeable.

"No way, I think you're extremely classy. Fuck that jerk if all he can see is a cute ass in vinyl." I regret the words the moment they leave my lips. He smiles at me as I blatantly cringe at my own candid statement.

"You think I have a cute ass?" His grin widens and he pulls himself apart from me a bit to glance me up and down dramatically. "What else haven't you told me, I wonder?"

//The jig is up. He already knows now, you might as well tell him how you feel. It will boost his ego, even if he does flat out reject you.\\ I open my mouth to speak and my jaw merely hangs there limply. Those big blue eyes of his stare wide into mine, waiting for me to try and put into words what's been making my heart and balls ache for the entirety of our friendship.

Without even thinking about it, I lean over and kiss him. Inside, I'm berating and screaming at myself for this stupid mistake, convinced I was about to be smacked again. To my utter shock and delight, however, Travis moans against my lips and reciprocates. One of his slender hands rakes through my disheveled hair, and the other slides over my shoulder and onto my back. I inhale audibly and pull him as close as possible to me by his waist. Within moments, the kiss gets more heated, our tongues lash about and duel passionately, unable to get enough of each other. His long, thick nails scrape up my bare back and I break the kiss for a moment to let out a deep grunt.

"Ughhgod, I love you!" I blurt out gutturally just before he pulls me back into the kiss. My hands roam freely over his thin, athletic frame until both of my hands are rested under each of his plush ass cheeks. Without parting lips, he straddles my lap and wraps his arms around my neck, pushing that satiny tongue deeper into my mouth. My palms massage and knead those soft, full ass cheeks. In this position, his bare, rigid cock rubs up roughly against the equally as rigid package in my pants. I use his ass to push his hips down harder onto my crotch. He moans and pulls away, shoving my back down flat onto the bed, and then lying down on top of me to kiss me again.

I wind my arms around him and flip him over onto his back, adjusting ourselves so we're further in on the mattress. "Ooh! Be gentle with me." He grins up at me seductively, wrapping his gorgeous legs around my torso.

"It's okay, I'm really new at this guy/guy stuff." I lean down and kiss him again. "The kissing and petting I'm good at…but…" I pant breathlessly in between kisses and nips at his neck. "I don't know what to do with a guy…I mean, I've never…"

"Mm…don't worry, darling, it's so deliciously easy…" He licks and chews on my ear and I let out a soft moan. "When we're through, you'll wonder how a woman was ever able to please you before." His hands roam all over my sides and back, sliding into the waistband of my damp trousers to cup my ass, pulling me harder onto him.

"Mmm…I don't doubt it." I barely gasp out as his tongue plunges deep into my mouth again. My hands trace over his lean, hairless form, a wonderful haze of passion and desire overwhelming me. This is like a dream come true. Everywhere his skin touched mine felt almost unbearably hot. My cock throbs and pumps out precum into my underwear and I squirm around on top of him, trying to lower my pants, not willing to break our kiss long enough to do so. He eventually helps me and before long, we're both utterly bare, writhing against each other, groping, grasping and clawing desperately at one another like sex-starved incubi.

"Tell me you love me again, Theo!" He cries out as I take one of his nipples in between my teeth. He grabs two fistfuls of my hair and holds my head down, urging me to keep going. His pulsing dick spews a few drops of pre onto my stomach. I reach down and take a firm hold of it. He lets out a breathless, broken moan, his grip on my hair tightening.

My jaws release the sensitive pink peak of his nipple and I gasp out through gritted teeth, "I love you, Trav...man or not. I've been craving this body of yours since I met you." My fingers size up the rigid length of his cock, he tosses his head back and whimpers.

"Oohhhmygod.....you ...seemed so straight, I was afraid to get near you..." He reaches down to tease my bloated cockhead with his fingertips. I hiss in through my teeth. It goes from teasing touches to outright stroking each other. We just lie there and jerk each other off and kiss madly and it felt like pure heaven, like it couldn't get any better than this. He suddenly pushes me down flat on the bed again. At first, I give him a questioning glare but then I see him lick those fat, plump lips and slide down towards my aching groin. Part of me wants to tell him he doesn't have to. The other 99% of me wanted it more than anything.

He glares up at me with a look that makes me want to melt in my skin from lust. I bite my lip and glare back at him, watching him wrap those lucious blow-job lips around my rock hard member. My eyes glaze over but I force myself to continue watching him, both of my hands entwined with his long, damp raven locks. His warm, velvetty mouth is a hundred times better than his hand, especially when his fingers tighten around the base and slide up the shaft upon every upstroke of his tongue. It feels like he's sucking the air out of my lungs, but it's because I'm gasping and panting like a dog, sweat pouring off my temples because of how torturously sensitive he's getting me; but I love it. He makes my whole body tense and thrash around him. With his free hand, he presses and kneads my balls, and I just know he's keeping me sensitive because he doesn't want me to cum. He's drawing this out as long as possible, not that I mind.

The hand he's been pressing against my nuts slides down so that the pad of his thumb is wet and pressing up against the opening of my ass. I groan and flinch in protest but he just keeps lapping over my oversensitive prick, making me gasp and shake all over from the intense arousal. I can't manage the word "no"...it's like the word simply vanished from my vocabulary. All I can muster is a breathless mantra of "Oh fuck, oh fuck, oh fuck..." as his thumb peirces my relaxed sphincter and dives deeper, inch by inch into my hot, virgin ass. My body responds by arching a bit off the bed to push that intrepid digit further, deeper inside me. It becomes wetter as he drools on it every so often on his way down my tensed shaft, now harder than it's ever been. I grind the back of my head into the mattress and let my body, my raw need take over.

He groans against my cock and pushes himself all the way inside me to the knuckle. His finger burns inside me and my ass clenches a bit around it. I always imagined something in there to be unbearable painful, and it was painful, but all I wanted was...

"More!" I gasp out in blind passion, suddenly so close to cumming and more crazy with arousal than I'd ever been. "Ohgoddammit, Travis, I need it!!" He eases up on my cock and just concentrates on licking the head, all the way up and down my veined shaft and over the piss slit. His sopping wet finger slides out of me halfway, then thrusting it back in with a single stroke and I cry out in a mixture of searing pain and blissful ecstacy. It goes deeper now, my ass is offering little to no resistance. He lets me get used to the meager girth of his finger, working my cock, getting it all sensitive to distract me, knowing it wont make me cum but it feels too good for me to make him stop. He begins to fingerfuck my ass, working me up to the second finger that he soon pushes inside me. I'm utterly insane by now, grasping desperately at him, begging him to just fuck me already because the need to cum is eating me alive. He saws his two fingers into me mercilessly and for a few moments, I feel a build-up but he denies me yet again. I curse loud and angry at him and he just chuckles. That's about when he ignores my cock completely and just works my loosened ass. And I lie there and take it like a gasping, squealing whore.

He grins like a Cheshire Cat when he sees me actually pushing back against his invasion. "Mmm...you love that, don't you? Just wait until you're riding the real thing, baby."

"Give it to me, Trav, PLEASE!!" I sob into my forearm, pushing my ass back into him. I've gotten so used to it, I can barely feel it anymore. And just like that, he decides I've been humiliated enough and slides his fingers out of me. That's when I feel more drool splash over the gaping opening that is now my ass. The thick head of his dick presses up against me and I groan, arching my hips up in offering to him. Somewhere in my head I want to panic. //This is the official step,\\ I think to myself. //After this, there's no going back.\\ He thrusts his dick into me slowly and it's sooo much bigger than his fingers, I let out a hoarse cry, my whole body tensing and shaking. He reaches down to stroke my cock, still amazingly hard from all this stimulation. //This is what I need...\\ is the answer resounding in my head as he enters me to the hilt. My scream comes from my balls and I swear I've never felt this good in my life. I spread my legs for him. I even reach back and pull my ass cheeks apart so he could get it in deeper. He begins pumping me and he hunches over, grunting, sweating and using my shoulders to push himself into me deeper. He looks more like a man now than I've ever seen him and he's still so beautiful and I'm still so madly in love.

"Tell me how good this feels....how much you love it!" He lowers himself down on me, now holding my legs back, pumping me hard and fast, like he means it. My cock is rubbing up in between our stomachs and it's driving me nuts.

"Oh god, fuck me, baby, I would do anything for it!"

He gives me a triumphant growl, lifting his head to force his tongue violently down my throat. I reciprocate wildly, arching my whole back off the bed at this point to meet his thrusts just to feel how deep his member piledrives into me. He tears away from my mouth and licks the side of my face, grunting lowly into my ear. "Congradulations, you're officially an ass whore. *MY* ass whore." I shudder as he says this, even though it's just getting me more turned on.

"Oh god, yes, I am!" I choke out, feeling my climax build as my cock rubs just right against his stomach amisdt a pool of our mixed precum.

"Seeing as how you need my cock so much, we're going to be a lot more than roomates now, aren't we?" He nips at my neck again, slamming himself in and out of my abused canal with the growing vigor that could only come from impending orgasm. "In fact, I don't even think we need seperate bedrooms anymore..except for show. We'll act plautonic to all your little friends, but when they leave, you know you'll be bending over, begging me to fill you up again, won't you?"

I'm right at the edge and I can barely speak. I'm gripping onto his body so tight, my eyes shut, my mouth hanging open. "Fffucckk yeah.....I'll spread my...ass for you anytime you....oh god...."

"You thought that because I dress like a woman I'll be all submissive...how does it feel to be my depraved little faggot, Theo?" He grunts, leans down and sinks his jaws into my neck. I shriek in pleasure as the orgasm hits me unlike anything I've ever had before. He rocks against me as my cock explodes, splattering my cum in between us. I scream his name as I pulse and clench around his swollen dick, feeling exactly like the depraved little ass whore he's made me into. He moans and continues to force his way into me, past my now tensing pucker as the blinding orgasm subsides. He bites into me again, his whole body tensing, spearing into me and my ass is so raw and loosened that all I can do is lie there as he uses me as a hole to get off in. He pushes it into me as deep as it would go and groans loud against the reddened flesh in between his teeth as he unloads his thick cream deep into my bowels.

When he pulls out, we both collapse, and I'm left feeling empty. I cuddle as close as I can to him and try to catch my breath. He wraps his arms around me and we plant soft, weak, yet loving kisses on each other, in the shower, and when we curl up in my bed together. He's wearing that hot little nighty and despite that phenominal orgasm I had earlier, I'm rock hard the entire night.

That morning, we discuss what kind of changes are going to be made around here, since we're going to be lovers from now on. We would sleep in my room but he'd keep his stuff in the other room so no one would suspect anything. He'd be dressed as a woman when he met my parents, and we'd tell my folks we were indeed serious so they'd get off my ass about marraige. That night, I finally went to his stupid show. Mainly to look for Robert, but he wasn't there. He'd called and quit, probably after sobering up and realizing he might be arrested for what he and his asshole friends pulled on my poor baby. That won't stop me for trying to find the guy. Honestly, Trav's show wasn't all that sexual in nature, and I thoroughly enjoyed it. Ironically enough, his parents were there and they were really cool people. I had to mentally smack myself later for being so worried about everything. His parents were so glad he'd found such a nice, caring, clean-cut guy with a decent job and a nice apartment that they took us out to dinner to celebrate. After they went home and we went back to our place, Travis kept his promise to me, especially since he was so pleased I'd finally went to see him perform. He forced me over the arm of the couch, lubed up my ass and took me all over again. I gotta admit, I'm loving this living arrangement, and I'm having more fun being an ass slave than I could have ever imagined. That was some smile Lady Fortune had for me up that sleeve of hers. She answered the prayers I didn't even know I'd asked for. Just goes to show you....some things really aren't too good to be true. Sometimes they're just good enough.