Trivial Pursuit: A Memorable Session with Ex-boyfriend

This month marks the 9 month anniversary of my breakup with my Thai boyfriend.  We parted amicably and today we are still friends.  He still meets me whenever I visit Bangkok and we had sex couple of times after the break up and we still enjoy each other's company.  No photograph showing his face as he is a celebrity and people will recognise him.  Even his dick is recognisable as it is uniquely large for an Asian with a thick vein running right down the top.  He is a romeo and I am sure all those pretty Thai models and beauty queens who were laid by him will remember and recognise his dick too.  

Anyway, here is a story of one of our most memorable sexcapades while his wife was away on a business trip. This took place in one of Bangkok's top hotels several years back:

"Amateur," it was half-question and half-challenge.   Tosh glanced away from the Thai X-rated movie on the television and looked at me as he answered, "yes, I think you are an amateur."

"No way I am not an amateur bottom,” my expressed a combination of fake pout, fake insult, and genuine amusement.   "If you say so," Tosh replied, turning back towards the television.

"I've had my fair share of dick - you should know, mister friend with benefits," I lightly kicked Tosh, trying to get his attention again.

Tosh looked across to me, sprawled out on the opposite end of the couch.  'Looks like we'll be finishing the movie another time,' he thought. The Thai businessman had been friends with me for about a year now, when he ran into me, at a company function at that time.  It was at a New Year's eve gathering where we first met.  The "benefits" had started that same night, and he was definitely familiar with my appetite when it came to men. He smirked in response, "I didn't say you were a virgin. Just that you can't take it for the long haul."

I retorted, "okay, what would it take, in your opinion, to not be an amateur?"

'This should be fun,'  Tosh said aloud.  "Hmmm... two hours.  If you're not an amateur, you should be able to bottom for two hours without whining about it."

"Two hours," I glared at him, annoyed at having my abilities questioned and debating in my mind whether or not I should take up the challenge.  A Cheshire grin indicated that he was game for me to take up the challenge. "Okay," my entire demeanor indicated that I was aiming to win as I couldn't resist a bet.   "Two hours. Blow jobs included?"

Tosh shifted a little, his pants suddenly feeling a bit tighter. "Sure, but not too much. It's about bottoming, not a hot dog eating contest."

I laughed at his joke, before I turned my body so that I was sitting upright. Leaning forward, I crawled between his legs and began playing with his zipper. "Let me know when you've had enough of my mouth."

Tosh leaned back, arms crossed behind his head, looking forward to the easiest bet he'd ever made. Literally, heads he would win...and he'd be winning tail too. He watched as his pants were undone and pulled down, exposing his expensive Derek Rose boxer-briefs underneath.

I pressed my mouth to the blue fabric, nudging into the hardness it concealed. I looked up, smirking as I took the waistband in my teeth and slowly pulled them back, revealing my prize and a favorite toy - Tosh's cock. It popped up, smacking me in the jaw before landing on Tosh's stomach with a smacking sound.   It throbbed as it continued getting bigger and harder.  I reached out and ran my tongue along it, from base to tip along the thick veiny shaft. Taking it in my hand, I licked the tip like a lollipop for a couple of minutes before sucking it in, between my lips.

I looked up at Tosh as I licked the head with the tip of my tongue.  When Tosh opened his eyes, I maintained eye contact as I sucked hard and pressed down, very slowly making the thick dick disappear inch by inch into my mouth. Tosh watched, partially enjoying the show and somewhat suffering from its teasing.  But he resisted the urge to pump his hips up, forcing his cock in sooner. His patience paid off when my lips finally made contact with the base, having engulfed his meat entirely.  Tosh shut his eyes and sighed with contentment as he ran his fingers along the back of my head.  He always does that to show his appreciation for a job well done.  I heard him moaned lightly, the sound causing vibrations up and down his pole, especially the head which was firmly buried at the back of my throat.  I could feel it flex inside my mouth as Tosh began a light pumping motion, trying to cram more his cock even further into my oral cavity.

I placed my hand flat on Tosh's hip, preventing him from thrusting too deeply down my throat and gagging me - yes his organ is huge and thick.   Instead, I began sliding my mouth up and down his fully erect cock, building up speed until I worked my way up to "full blowjob mode",  as how Tosh would describe it.   He knew that I could lose track of time and the world when I am fully engaged in the act of giving head.  With a cock in my mouth, everything else around me becomes lost to me except the cock running in and out of my mouth.   And not that he minded one bit ... in fact, he rather enjoyed the fruits of my labour.

At that moment, I was in fact becoming  lost to the world; the only thing that existed for me was the taste of Tosh's heavy meat on my tongue and the musky scent emanating from his pubes, infiltrating my nostrils.  I didn't stick with any technique for very long; for a few moments I would have the head between my lips while playing my tongue back and forth, then I would be deep-throating the entire piece of meat.  Occasionally I pull off and give the shaft a good tongue-bathing, along with his heavy nuts below.

A while passed with Tosh stretched out, head on a pillow, enjoying my oral ministrations between his legs. Opening his eyes, he noticed the clock and saw that a half of an hour had passed.  Reaching down, he ran his fingers through my hair...then gripped it and pushed my face down, burying his cock in my mouth and grinding his hips up for a moment before holding my face and pulling his cock out from my mouth.

"Time to switch, it's been a half hour already," Tosh said with a wink.  I nodded as I stood up. "Okay, let’s switch.  My jaw was getting a little sore anyway from sucking your big cock."

"Hate to break it to you. but something else is about to get a lot more sore," Tosh replied, untangling his feet from his jeans and underwear as he stood up.

"I can’t wait much longer," I responded and then bounced off, disappearing into the bedroom.  His shirt landed on top of his jeans and underwear, his raging hard cock bouncing in front of him as he made his way to the bedroom as well.

He came to a halt upon entering the room.   I had already removed my clothing and was lying down on the bed.  I had changed into a pair of jock strap.  I was propped up on the pillows with my hands crossed behind my head, legs spread out wide open, invitingly.   I lifted one leg into the air, exposing a bare butt cheek.  “Hope you like what you see, Mr Tiger.”

Tosh needn’t have to answer that question.  His already-hard manhood throbbed, becoming impossibly harder said it all. "I think I hate you," Tosh growled with a fake glare. I lowered my foot back down to the mattress and then brought it back towards my hip, my knee up in the air.  The movement exposed a hint of bare ass and crack, nestled between the mattress and the white pouch of the jock-strap which was straining from my own hard-on. "You know you love it."

Tosh ignored me and closed the distance from the door to the bed. Lifting my foot again, he gave a firm swat to the uncovered cheek. "Maybe," he grinned. I flinched a little from the swat before returning the

grin. Wresting my foot free, I placed it against his chest and gave a light push. Obligingly, Tosh fell onto his back, sprawled across the mattress. I pounced, landing on top and straddling him, began to rock my body from side to side on my knees.  Smiling broadly, I asked,  "how do you like it Tiger?"

Shifting my weight, my ass made its way back until it made contact with something hard; Tosh's cock was quickly nestled against my butt like a hot dog in a bun. Slowly, I began moving my hips, so that the tip of his dick slid up and down the crack of my ass, slowly at first but with a slightly increasing speed and firmness. Tosh gave out a slight moan when he felt his cock head nudge up against my hole, before sliding back up again. Once again, his cock brushed against the entrance into my ass, over and over, each time a little longer.  I moaned as well, causing him to open his eyes again. I was sitting atop Tosh, rocking my body, grinding my bums hard on his erect pole.  Eyes closed and head tilted back, I was biting my lower lip with pleasure ... a pleasure which was also evident by the stretched out material of my jock-strap pouch.   Tosh ran his hands up along my thighs and reached further back, grabbing an ass cheek in each hand.  I pushed back harder, enjoying the feeling of his hardness...and the tip of his cock, placed at the entrance to my boy-cunt.   I sighed and ground down and with a light push downwards, I could feel his  cock head entering inside me as he pushed his hips upwards.  Tosh squeezed my ass in his hands, preventing it from moving away from his body.  I lowered my body down against John's, nuzzling my face into his neck. "Oh god, how does your dick always feel so damn good?"  I groaned while tightening  my sphincter muscle, causing it to squeeze his still-embedded tip; it was so tempting for Tosh to grab my hips and impale my hungry anal orifice, giving me what I needed.   Tosh obliged me by sliding the head in and out a few times before withdrawing.   He tugged my face up and kissed me deeply. "Get the condoms and lube, I can’t wait to fuck your tight boy-cunt."

I rolled off and over to the edge of the bed and rummaged through the drawer.  Tosh sat up on his knees and moved behind me, waiting. When I found what I was looking for, he grabbed me by the hips and pulled me back, so that I was on my hands and knees. Leaning forward, he took the condoms and lube...all the while grinding his hips against my buttocks, eliciting a soft moan from me.   Settling back, Tosh opened the lube and drizzled some of it down onto his cock.  Then he let his lubricated erect pole slide back and forth between my thighs, spreading the liquid along my crack. He smacked his meat against my hole a few times before allowing it to rest there for a moment; there was a heat that came from my ass that Tosh loved to feel against his hand, and especially against his cock. Teasing, he nudged my anal entrance and watched as I gripped the sheets a bit and shifted his hips up, eagerly waiting to be mounted. 

The sound of tearing and some rustling filled the room, and then silence...followed by a yelp as Tosh popped the head and first inch of his dick into my tight hole. He knew that the yelp was more surprise than actual pain.  I loved being filled, and Tosh was willing to oblige. Back and forth, he ran the first inch or so in and out, pulling out until he could see the rim of his cock head before burying the shaft again. My toes curled up against his calves, signaling my enjoyment.   My fingers gripped into the sheets as Tosh thrust forward, slowly sinking inch after inch of his thick cock into my hungry boy-cunt.  The shaft was thick with a huge bulbous head that really can fill up the emptiness in me .... this is one of several reasons why I loved bottoming for Tosh.  "Oh my gosh, it feels amazing,"  I whimpered out loud more than once. "It keeps stretching me out while you're still filling me up...drives me crazy for your cock."

Tosh watched as I repeated those words over and over as my fingers entwined into the sheets and the muscles of my back and shoulders flexed with pleasure.  I curved my back down, towards the bed, causing my bums to point up as I pushed them back, trying to force myself onto Tosh's erect cock, half of which had already disappeared inside of me.  Tosh placed his hands on my cheeks, preventing any further movement backwards. Spreading my cheeks apart, he began moving back and forth again, loving the sight of his cock being swallowed by my hungry hole, feeling my bums pushed back tight against him, eager for more.  There were only a couple of inches left; so he moved his hands up to my hips and gripped them before giving a hard thrust forward, burying the last of his thick meat inside.  My shoulder dropped to the mattress, face pressed to the pillow, mouth open, as I yelled out, "Arghhhhhhhhhhhhhh, yes, fuck me, fuck me, please fuck me, harder, harder …”

"Okay, baby, here it comes," Tosh replied.   I turned my head back so that I could look at him.  His fringe was matted down on his forehead and his eyes had a half-lost glaze of lust in them.  I gave him a wicked smile as I began crooning about the thick cock inside of me, how much I was enjoying it, and asking to get fucked harder and faster.   Tosh responded with quiet agreement - he withdrew half of his dick and then slowly sank it back in again, grinding his hips into my ass.  I buried my face back into the sheets and moaned as I pushed my buttocks back to meet his body.

Tosh decided that prep time was over, and began enjoying the pleasures of my boy-cunt earnestly. He no longer sank his cock into my hole, but started ramming it in and out.  The sounds of skin smacking into skin and his balls smacking against  me filled the room, along with grunts, moans, and sighs.   I begged for more and Tosh ran his hands up and down my smooth back, telling me how good it felt to have his cock buried inside of me, as he pounded away at my ass.

The fucking went on for some time, the rhythm, speed, and intensity varying.  Both of us were covered in sweat in spite of the air-conditioning, and from our physical exertion.  Tosh's pace began slowing down as his thrusts became harder and longer.  These were signs that I could well recognized – he was nearing the edge.  Glancing at the clock, I saw that two hours hadn't yet passed and I wasn't going to lose the bet on a technicality. Taking control of the situation, I slowly moved my body away from him until his cock was entirely withdrawn.

Turning around, I pressed my chest up against Tosh's, grabbing the back of his head and pulling him in, and began nibbling along his neck.  My hands roamed around his back, squeezing his shoulders and his firm buttocks, as my mouth moved to his ear, caressing it with the tip of my tongue.  I was determined to keep his arousal up, while bringing his libido back down to earth.  When I was finally satisfied that Tosh's body had calmed down a bit, I began to French kiss him.  I gave out a soft moan when his fingers found my nipples.   We continued to kiss as Tosh played with my tits, tweaking them the way that he knew I liked. 

After I was satisfied that Tosh had calmed down enough, I moved back towards the middle of the mattress, guiding him along with me.  I lay on my back as he moved in to lie on top of me.  My legs wrapped around his waist, happily pinned beneath his weight.   Tosh easily understood what I wanted and readily guided his cock between my thighs and buried it into my hot and eager boy-cunt.  I moaned happily as he entered me.  I wrapped my legs more tightly around his waist, silently begging for more.

Tosh resumed fucking me but at a slower pace than before.   Now that his thrusts were calmer, John was

able to enjoy the way that my sphincter was gripping his cock as it pistoned in and out of my hole.  My hands dug into his shoulders as my lips and tongue played along the his neck, ear, and chin.  My toes curled each time I felt his hard shaft plunged inside of me.  The insertion usually elicits a soft groan from me.

After some time, I begged for more and Tosh gave it to me, maintaining a slow and steady pace but

pounding harder and harder.  He lifted himself up on his arms, getting a better angle to begin plowing me again.  Both my ankles were now resting on his shoulders, granting him easier access to slam his hard erect cock into my hungry boy-cunt. At that angle it is also easier for him to slowly draw his cock out...only to slam it in again.  After some minutes of getting fucked in this fashion, I had devolved into speaking gibberish, my own erect cock bouncing around in time to his thrusting. This time it was my own orgasm that threatened to cut our time short. Reluctantly, I slid my palm down Tosh's chest to gently push him away.  Then immediately, I pushed him onto his back and straddled him.  This was his favourite position, to let me bounce up and down on him like a cowgirl.   I bent down and kissed him deeply as I teased the head of his cock again, popping the tip in and out of my hole. Tosh grabbed my hips in his hands and pulled them down while thrusting his own hips up, slamming his rock hard cock into my gaping hole.  I gave out a yelp.  I placed a hand on each of his pecs, enjoying the feel of flesh and muscle. Gripping him tighter, I began riding up and down, meeting his upward thrusts.   Tosh grabbed my cock and began stroking it as he continued fucking me.  I was leaning back, my hands holding on to his thighs for support as I rode his dick below me as I thrust my own dick into the hand that was grasping it tighter and tighter as I rode his cock.

My boy-cunt began clamping harder around Tosh's pole as I rode him.  I could also feel my own erection throbbing harder as it moved  in and out of his hand which was holding on to my cock.  I didn't care a fuck about the clock - my ass was getting sore, in a way that felt good, and my own nuts were screaming for release. 

I rode on Tosh's cock fast and furious.  I could hear his breathing getting heavier and heavier.  He began to groan very loudly as he shouted out to me, “ cummminnnnnnggggggg…. I am cummmmminngggggg.”  As he neared the point of no return, he somehow remembered what I liked most.  Pushing me away, he moved himself upright and leaned over me.  He removed the condom and aiming his throbbing cock at my face, he continued to stroke his cock furiously.  I moved my face nearer to his cock as my hand took over from him.   I continued to fist him violently until he at last, screamed out loud, “here it comes, honey, here it comes,” as his cock twitched and started spouting out thick globs of spunk.  They landed all over my face.  I counted at least nine shots before he moved back and falling over me, hugged me and began to kiss me hard and deep on my mouth. 

After Tosh had recovered from his orgasm, I sat back and asked, "how was that?" He ran a hand up and down my thigh, giving it a squeeze. "You're not done just yet, but that was damn good, and..." He glanced at the clock, "two hours and twenty minutes.  You are certainly no amateur."

I was going to get off the bed when he said, "I said you weren't done yet."   Tosh was amused by the confused expression on my face as he flipped me onto my back.  He straddled me and inched forward, until his crotch was right in my face. As he began stroking his cock, a look of cheekiness crept back to my face as I comprehended his words and actions.  Licking my lips, I pulled myself up slightly, leaning against the pillows, running my hands up and down his thighs.  Tosh reached down with his free hand and grabbed the top of my head as he leaned closer, his hand furiously stroking his cock.  He yelled out as he began cumming again, shots firing through the air and slamming against my face, chin, and neck. The last of it dribbled out of his pee-hole, landing on my chest.

"Wow..." I hadn't seen Tosh cum like that before, twice in a row. "Impressed?" he asked with a smirk on his face.  I looked up at him and replied, "Am always impressed with you and your dick."

Tosh decided to give me what he knew I liked most.   Leaning forward, he brought the head of his dick, still wet with cum, up against my chin, smearing it into the cum that had streaked across it.   He quickly moved his cock up, bumping it against my mouth.  He nudged my lips teasingly, before pushing more firmly, parting them.  I latched my mouth onto the still-throbbing meat as it drove further in toward the back of my throat.  My hands squeezed the cheeks of his bums as my mouth worked, swallowing as best I could with my lips wrapped around his erect pole. Tosh ran his fingers through my hair, enjoying the sensations before his penis became too sensitive. Slowly, he pulled out, watching as I maintained a tight deal with my lips until the head reappeared with an audible popping noise.  I gave a slow lick along the softening shaft, from head to base, before falling back onto the pillows, a satisfied smile on my face.

Tosh lay down next to me on the bed, our feet tangled up, enjoying the feeling of being near one another, and the post-orgasmic bliss, before nudging me off of the bed.  We definitely needed a  shower to get rid of the scent of sex from our bodies.