From cyber to losing my virginity

I had always been a straight guy and to this day i still more or less consider myself somewhat straight, i do not ever recall that i had ever harboured feelings for a man and i dont think i ever will. I had discovered porn at the rather young age of 12 , i had been with a friend that day waiting for my mum to come pick me up at high school some older boys at school had been teasing me about ever watching sex vids.

i remember i had played it cool and lied, telling them that it was common hobby of mine and they had laughed pretty hard asking all sorts of details to check if i really had grown the balls to do that yet, i had to try reall hard to recall every sex scene from late night movies to try and bluff them again. I dont really remember if i did ever convince them or not but i do remember that on the trip back home in the car , that conversation had sown the seed of interest in sex in my young innocent mind, previously home only to my cartoons , stories and games... a touch of taint in my mind.

Over the weeks i had managed to search the entire house till i discovered one of my dad’s porn VHS cassets, i still remember the rush of hope that i might have finally discovered what my young mind consiered the holy grail of debauchery! The fierce rush of adrenalin after i had placed in the video player and saw the woman that would be the sex goddess of my wetdreams for years to come, Tracey Adams in the movies “pussy Jobs”, come to think of it, the music is still in my head many years later !

That had been the start of my decent into porn, experimenting with masturbation trying to recreate the feelings the actors in the movies were experiencing by jerking off with various lotions and motions. Over the years i had gotten my own routine down and knew what i liked and guessed it was pretty close to the real deal, but one experience i had never managed to guess, anal sex.

It was always somthing that i found so curious, trying to imagine how the guy felt while pounding away at some young harlot’s ass and how it was different from her pussy. So one day i had lubed up a finger and gently slipped it into my very tight virginal anus, i remember the sheer feeling of kinkyness making me rock hard at the discovery of the warm, moist undulating surface of my ass, from that day on when ever i had been jerking off to an anal scene i had been imagining my dick surrouned by that heat and texture.

However one day when i was around 18 another thought struck me, this time far more alien to my mind at the time , i wondered what the girl was feeling on the other side since after all her clit was on the other side wasn’t it? What could be giving her so much pleasure and making her moan that much? So one day , in the privacy of the bathroom, i had tried to lube the thick smooth handle of my hair brush and push it in my ass while bending over, i remember the searing pain i felt as the smooth piece of wood tried to pry my tight virgin anus open and abandoned it right there , standing up and clenching my buttocks shut wincing. It took me a few days to manage the courage to try it again this time with a much smaller candle with a tapering end of about 1 cm to around 4cm at the most . i had found it a rather curious sensation, not of direct pleasure like masterbation (since the concept of prostate stimulation had never occured to me at that point) but the sheer kinkyness of the whole affair left me with massive erection and a budding interest of how much pain would be involved for a dick to fit in there and the feelings afterthat, but i dropped the idea since i would never let my ass be fucked by a guy ...... boy was i wrong!

That had led me to start reading about anal sex stories and i had stumbled across a gay story site one dark night , i was on the point of closing it when i decied to just read one of them, i had found them somewhat icky reading about sucking and tasting a guy’s penis but then my curioustity had been pricked when i read bout the pleasure the characters were recieving from getting fucked, an orgasm from getting sodomised ? wow that had never occured to me.... hmm maybe one day i might.. no no... am sure i will never get fucked down there, hell i wasnt likely to come back to the site again right ? , sure, totally sure..... well sort of sure.....

Cut to a few years later i was almost ready to enter college!

Reading gay sex stories had become by then an occasional thing to get off, maybe once in a while i’d try it to get a change of pace from guy-girl fantasies but i had started to wonder if i could get a gay guy’s take on the subject but i didnt know any of them so i buried the idea till someday i discovered adult friend finder!

I was quite suprised to discover how large the number of gay men there were in my rather backwards country, but alas since it was impossible to contact anyone without paying i was stuck with browsing the member thumbnails , consisting mostly of shots of their dicks, untill.....wait..... what ? can he do that ???? one guy with a rather huge chocolate brown penis had put his email address in the username... it wasnt an email as such but it was written in code to bypass the site’s security validation to prevent that sort of thing, i had decied to email the guy and ask if we could be friends.

A week later i had recied an email from “steph” saying sure and gave me his msn add so we could chat someday, and indeed i saw his name with a little green symbol next to it one late night and with an odd flutter in my chest i said hi...

Over the course of the hour we had started to get to know eachother gradually nearing the topics of adultfriendfinder, if he had met people on the site, and of course my curiousity about gay sex, he had started to flirt around with me when i told him about my experientation with my fingers and told me that was just toys compared to what a real thick warm penis can do, he had been very eager to meet me , i played it coy saying i had really strict parents, i had still been living with them at the time, and i can’t go out much at night.

The rest of our irregular chats went like that for a few weeks or months with me warming up to steph untill he had asked to see my pics, i am a tall guy, 1m87, weighing around 85kg with a broad chest, i was perhaps a little overwieight especially in the thigh and ass area, i thought wat the hell, it might be interesting to see what a gay man thought of my body so i had taken a few shots with my webcam of me bending over and exposing my thick ass while kneeling one knee on the bed. He loved them, that gave me an odd little flutter in my chest that kinda made me blush, especially when he had told me graphically what he wanted to do with my poor innocent little butt and he sent me a few pics of his huge chocolate organ. Over time the idea of meeting him inperson didnt seem so fobidding.

So one day i had decided to accept his invitation to go for a ride with him in his car and perhaps some fun as he said it, i had figured he was joking though. i had been shy as the virgin i was when i waited for him to pick me up at the prearranged spot in town , he turned up in a white car pulling up to me and waving me in, i had hurried over to the passenger side my heart racing and my mind screaming “WHAT ARE YOU DOING ??! “

We drove around in thick traffic for a while looking for a quiet place to park and talk a bit, but it was almost impossible since all the schools had released their payloads of kids and teens so he said he was going to a bit out of town. We were driving through a rather quiet strech of road when he caressed my arm while driving, my heart skipped a beat, he wasnt joking about the “fun part”, since i didnt object he went further... his hand slipped under my butt , cupped a buttock and squeezed. That made me gasp and he chuckled asking “alor sava?”, so ur ok ? in french... i mumbled that i was ok and smiled blushing deeply, he kept on asking coy little questions , not directly referring to his squeezing hand till we left that quiet road and he drew his hand to shift gear.

The conversation had turned to sex and i had started to relax more in my seat , we had been driving along almost on the highway when he slid his hand into my lap and gently squeezed my groin, he told me to open my jeans a little and numbly my hands moved and i did it, steph purred thats it...“hmmm voila , c’est sa” as his hand slipped into my jeans and moved first over my underwear till he pried them aside and slipped his cool finger around my semi hard dick and lower to sqeeze my balls. He drew his hand back everytime a car or truck passed us by then did it again a few more times till found a nice shaded spot near the cemetary to park, aside from the occasional bus it was quiet and he kept fondling me , we talked a little too about my past experieces concerning sex till he got a phone call from one of his music students he had to tutor later on. Apparently the little bitch has asked him to come earlier that usual he told me and he was rather pissed since it had taken us awhile to find our little spot and longer still to get his hands on an innocent cherry guy.... he said he had to drop me off quick and rush but he didnt want to just let me go without doing anything to me, i was like “huh? What do...” he told me to take out my dick completly free of my jeans , i did so without thinking and i stared in suprise as he suddenly turned and bent over my lap and took my 6.5 inch dick in his mouth and started to blow me,

I drew in a breath in shock and i pressed my back into the seat! I wasnt expecting that, the feeling of warmth and his tongue running over my shaft stunned me till i gasped that a stream of traffic was coming our way from behind, he drew back, cursed and said that it would have to do, referring to giving me a little taste of gay sex, but had he been referring to the act as setting bait to get me into his bed, he coudn’t have been anymore spot on!

This little epizode had given me jerk off material for sometime while steph and i chatted, he asked how i liked that day and told me that if i wanted more, i knew where to go, his place. But that was something surely even i would not do... surely that was far too much.... wasnt it ?...
Well after a while of irregular chatting due to my studies at college he and i had been doing occasional cyber sex he started asking me again to come over at his place and let him have some fun with that ass of mine, the thought of another guy openly asking to fuck me seemed an odd one though in a pleasant one, he occasionally joked about how he was going to turn me from a pussy fan to a pussy boy after a long through fucking, i always had a sort of a conversion fetish and that comment kinda turned me on although i doubted anyone could do that.
Then night i gave in, steph and i made plans to meet at his place, he told me to take the bus halfway and he’s meet me and give me a ride to his place, that very night i had shaved my pubes and ass since he had previoulsy told me he really liked shaved smooth bodies. The very next day, i had througly prepared my ass to doubtlessly going to be its inauguration day to the world of gay sex, had a douche i got from the chemist early morning and a shower, grabbed a new change of clothe and left to meet steph.

I arrived at the meeting point and he turned up on time to give me that ride, he greeted me warmly while my heart raced like mad again, a stituation not aided by steph who had decided to put his hand under my butt as i was sitting down and kinda rubbed his middle finger around my anus and asked smiling if i was ready for what he was going to do to me there, we reached his place 15 mins later and as i looked at his garage door i though well thats it, no more backing out, am going to be sodomised in the next hour!

We got inside and i paused at the door inside to take of my trainers and i heard steph purrring appreciatively as he watch me bend over , that gave me another nervous giggle and flutter as i asked myself if girls felt like this too when a man paid them the same sort of attention. We went to his room and i sat on the bed while he turned on the fan and asked if i would like a drink, i acceped a glass of cold water and chatted while i drank my knees feeling weak under me. When i was done he took the glass from me with a smile and asked if i was nervous i replied i was, he smiled and stood before me, he told me to relax and genlty but firmly pushed me back on the bed.

I slowly closed my eyes thinking this is it, am going to get fucked...

He ran his hands over my chest till he got to the buttons of my shirt and undid them, opening it up to expose my chest and stomach, he caressed me and told me i had great skin while his hand undid my belt buckle. He took off my belt with a tug and stood up over me gazing appreciatively like a man at a goot cut of steak, he chuckled and took his phone, he told me he was going to have to take his time to enjoy this as he made a call to one of his students he had scheduled during the day for tuition, he told her that he wouldn’t be able to come to her today and he’d get to her tomorrow.

While he talked he motioned to me to undo the jeans my self slowly as he watched, i did as he bade me to do and stayed on the bed watching him , blushing slightly. He came back to me and over me, he licked and nibbled at one of my nipples making me squirm and gasp and kissed his way down to my navel as his hands tugged and removed my underwear exposing my semi hard penis. He kept on kissing his way down till he reached my dick and took it in his mouth, the feeling of heat and a swirling tongue returned like back in the car but he kept on doing it, exploring even deeper to my balls, he sucked one into his mouth hard and held them there for a moment before releasing it with a pop, he repeated that a few more time much to my pleasure then deep throated my now fully erect dick.

He got up and tugged of his tshirt and took off his jeans as i sat up realising i was about to see his fat chocolate snake, my first sigh ever of another cock than my own. He stood infront of me looking at me as he slowly peeled out of the thight bulging boxer shorts revealing a HUGE and i mean it, brown cock, it was at least 8 or 9 inches long and maybe twice as thick as my own. I just stared in amazement, i later realise i felt the same way i read in somany erotic stories of timid women and girls seeing a huge penis and involuntarily feeling the hunger of touching it. I took it in my hands and ran my hand down its solid think lenght....

Then without even thinking about it.... brought my mouth to it, it was a automatic reaction, i had no control over it at all ! i had to open very wide and i took his cock into my mouth, the texture suprised me, his cock head was so smooth , almost silky and i anticipated a taste to it but there was nothing, no smell or taste, i went lower down onto his shaft hearing him purr and caress the back of my neck. This was suprisingly pleasent, i go to it with more effort copying all the blowjobs i seen done by hundreds of porn starlets , swirling my tongue across his head hearing steph moan in response giving me a feeling of accomplishment at my efforts to please, i licked from the base of his dick to the tip, the wet lengt of it smearing my own sliva across my nose and cheek, he was far too long for me to take in totally but i tried till i coughed and chocked on it. He pushed me back down to the bed and i lay on my side as he kneeled over me and guided his dick back to my mouth, i opened wide and accepted it in, this time he gently fucked my mouth slipping in deeper and deeper till i chocked and coughed again, he told me to lie down stragght and he put his arms under my thighs and lifted them, he bent down to my ass and spread my buttocks after gently biting each of them. I felt an electric shock as he gave my little rosebud a big lick and started to eat me out. The feeling was incredible, never had i felt such stimulation down there and it caught me off guard causing my body to squirm and writh on his bed, he held firm and kept doing it while i gasped for air.

Then he lied down right next to me and told me to get on him facing the opposite direction placing my ass over his face, he pulled me down placing us in the 69 position, i saw that enough to know what to do although i never thought i would be in the girl’s position though, i gave him the best blow job i could while enjoying what he was doing to my ass and cock with his tongue and finger.

I dont know how long that went on, things were a bit of a blur at that point, he told me to get on all fours doggy style, i was lose enough to be taken by that thick monster cock...

I did as i was told, getting on all fours like a little bitch in heat waiting for him anxiously as he got his lube out of this cubboard and a condom, i had made him promis that i wanted safe sex before coming though at this point i wouldn’t have care to remember to check. He put on the rubber and lubed his cock, i waited my heart pounding as he placed the thick flared cock head near my anus and started to push...

It simply hurt as my skin was being pulled taught across the surface of the rubber and he drew back, he tried several times but the pain of my skin being pulled across the gripping rubber was too painfull and the fact that his hands kept having trouble on guiding his pre cum covered dick in the lubed condom wasnt helping either, he told me that he was having trouble because of the damn condom and asked if he could get rid of it, in after thought.... perhaps that was a deception on his part to fuck me bare back but i my lust to be taken overtook my desire for caution... he smiled and streched the rubber over his dick , pulling it towards the base of his penis till the condom broke accorss the head with an audible pop! He ripped the rest of the condom off the base of his organ and tossed it aside, the lubed himself again and inserted a well lubed finger into me twisting around to spread a layer of lube in my hot little hole.

He placed the thick head again agaisnt my virgin little sphicter... some say the human body is designed perfectly, every feature to be for some purpose..... i guess steph’s cockhead was too, the thick wide flared head was silky perfectly suited for a task aswell.... that of spreading a little virgin anus wide and open...

He deflowered me, took my virginity, my innocence... call it what you like, it felt good despite the searing pain as his huge head speared through with little resistance my soon to be X virgin ring, there was no stopping it , no clenching would stop that unstoppable force... it slipped in, spreading and widening my opening causing the muscle and skin at the opening to streck and tear.

I gasped and moaned while biting into his bed covers as he invaded my most private spot as the burning pain and sudden fullness took my focus. He reassured me the worst was over , he gently allowed the weight of his body to lean into me as the rest of his shaft sunk into the ruins of my virgin cannal untill i felt his pubic bone resting agaist me , it was done, he had taken my virginity...

He gave me a moment for my ass to adjust to the invasion then he drew back a little and sunk in it again casusing my to moan in pain... slowly over the course of a few minutes he drew back further and further swinging into me with greater force driving his penis through my now ruined anus and loosened passage slowly rearraging my bowels to suit his fucking, he was turning my ass into his personal pussy. Sure enough the pain was going and each stroke was getting easier and more natural...my voice muffled by the bed covers

“ah..ah..ah...ah...ah...ah...ah..AHH...AHHH UUUGGGHHHH...” cried out louder as he struck my prostate and gave it a massage with his cockhead, the wave of pleasure that came with it blew away what ever inhibitions i had left and i started to meet his strokes back. We were in full fuck now, him humping at me like any man fucking a girl and me meeting him like a little harlot in heat, the room was filled with the sound of our fucking and moans. It went on for a while like that i looked under me and saw 2 drops of blood on the bed sheets trailling down my thigh, i didnt care anymore, my dick was fully erect and i reached down to jerk off.

I came within seconds, the solid sodomizing i was recieving, the massage of my prostate, the realisation that i was beign this man’s bitch and loving it was too much, as i came my anus clenched with spasms around him and that caused him to go into an overdrive slamming into me with reckless abandon about a dozen times as he filled my abused and ruin ass, i felt a sudden soothing heat spread deep inside as his semen washed away what little left of my innocense remained he left his penis in me as it softened, he rested his chest on my back kissing me gently on the back of the neck. He laughed and told me that now my ass was properly fucked as he drew out his cum soaked cock unplugging my ass causing a little rivulet of pinkinsh semen to come down my thigh right on the blood trails from minutes before from my now gaping anus...

I just stayed there stunned as i felt the semen dripping down my inner thigh and smiled before falling flat into his bed.....