My Journey: From Fingers to Coc

I suppose I should start by offering some background as to how I tumbled down the rabbit hole of my own sexuality and found myself in the situation described further on in this story.

I had always been straight. I knew it and everyone else knew it. With girls I would say I had average success due to my 6ft and reasonably athletic build. During college I would pick up girls on nights out or through dating apps but still only being 22 I never really felt like I wanted anything more than a single night of fun, and this habit continued until soon I felt like like plain vanilla sex just wasn't doing it for me. One night, after a sports team night out and a lot of alcohol had, this average looking girl approached me and before too long we were making out and jumping in a taxi back to her flat at the edge of town, (I preferred to go back to their place as it meant I could make a swift getaway before any awkward morning after chat).

So after 15 minutes of less than average performance from both of us I felt, she must have taken pity and offered to finish me off with her mouth which I was more than glad to allow, so she began what was, or at least started off as, a pretty underwhelming attempt to suck me off. Soon after she began though was when I felt it. That gentle finger circling and sliding south from my cock and balls at her chin. The sudden change in direction caught me off guard and my cock definitely jumped in her mouth, and she definitely became encouraged by my, all be it involuntary, reaction. Her finger was no longer just circling... it had zoned in and found its target, and I found myself unable to resist or pull away as she gently pressed her slender finger into my ass.

To be honest I was quite annoyed at how little resistance my puckered ass put up, and she was most likely surprised as well, but by that point she was curling her finger inside me and before I knew it a small audible moan escaped from my mouth. That was all the encouragement she needed and I could feel my climax growing as she licked at my cock and beckoned my insides with her finger, each time she thrust her finger back in my cock twitched. I couldn't even warn her before my orgasm started and I am sure it was longer and more powerful than any orgasm I had had before.

I gave that experience no further thought until a few days later when my housemates were out and thought I'd treat myself to some self pleasure. I opened my usual porn site and quickly returned to a favourite video of mine, 'Teacher takes schoolgirl in every hole'. I was so familiar with it I skipped to my favourite scene, where the girl is spreading her ass cheeks over the desk while her built hung teacher slips his cock from hole to hole. And then I found myself wondering while I jerked... could I? No, it was a one off. But maybe? I readjusted my position and reached behind me and slid my middle finger down my ass. I kept watching the video as I slowly applied more pressure and with a single motion my finger slid into my ass for the first time, the second time I had had a finger in my ass that week, and for the second time in my life also!

God it was good. With her it was dirty, a bit taboo. But with me I could find exactly what I was looking for and was able to experiment with different speeds, angles, and pressures, as a I probed my P-spot. The porn video had long stopped playing and I found myself with my eyes closed concentrating on rubbing my insides while I tugged on my 6.5" cock. I became so caught up in myself that I didn't even attempt to catch or direct the cum when it started spurting from my cock and continued to finger my ass as the cum landed on my chest and stomach and after the wave of euphoria faded I took stock of what had happened. My hand had been nowhere near my cock when I had cum, one hand was busy massaging my ass while the other was holding on to the bedside table for stability as I bucked against my finger, a true hands free orgasm I believed they were called.

I was hooked. This became my own dirty ritual I would carry out and routine wanking just no longer got me off. Over the next few weeks I continued to experiment with my ass and became very efficient at bringing myself to orgasm. One finger soon became two, and after two I decided to try the handle of a hairbrush. Bliss. The smooth plastic could reach greater depths than my fingers could, and I could really go to town on my hole by gripping the other end. Of course I had to buy lube for myself which felt a little embarrassing as the cashier scanned it and handed it back to me, but I can't imagine she once thought it was for my own hole.

My porn habits soon started to shift, I found myself drawn more to anal scenes either with toys or cocks, then girls using strap-ons on one another (big ones too), and eventually shemale scenes became a healthy staple of my dirty porn diet. Watching these beautiful shemales massage each others asses with their thick hard cocks made me realise I needed more... I needed a cock in my ass to replace my fingers and brush handle. Not a real cock obviously, I wasn't that way inclined after all and the notion didn't even enter my head at the time. Just a plastic one, a real dildo.

Within 30 minutes of research online I found one: '7 inch realistic dildo with suction cup mount'. Suction cup could be handy I thought, and while 7 inches sounded a lot to me looking at my own 6.5" dick, it was still small in comparison to some of the scenes I had been witnessing in recent porn viewings. 4-5 day delivery for my new toy... great.

Those days felt like an eternity and when finally there was a knock on the door I instantly jumped to attention, (pulling a finger out of my ass), before my housemates could answer it. If only the delivery driver knew that he was hand carrying a 7" plastic phallus that in 10 minutes was going to be fully filling my ass. So I dived back into the privacy of my bedroom and ripped open the box... god it suddenly looked even bigger than I imagined, and instantly my own cock began to grow almost as if it was jealous of being outsized and wanted to do its best to impress me.

I held the purple cock in my hands, rubbing my fingers down its thick veins, and was impressed at the likeness of it to the glistening cocks those shemales would suck and fuck. Suck... hmm... without even thinking I brought the cock to my lips and outstretched my tongue and flicked it across its head. Soon I had popped the whole head inside my mouth where I did my best to imitate those I had seen in porn, puckering my lips and letting my tongue roll around the underside of the dildo as I casually slid it in and out of my mouth. I tried to push it in further but I'd be lying if I could have swallowed more than half its length before I gagged a little and pulled it back out, but seeing the top half sparkling with my spit was an instant turn on.

I grabbed my lube and rubbed some over my new friend from top to bottom and with the excess left on my fingers I rubbed it around my twitching hole. I pressed the suction cup onto my small table and angled the natural bend in the cock towards me, and turning round to pull my cheeks wide I lowered myself down onto the slick hard cock in a smooth motion with minimal resistance as my ass swallowed its prize... fuuuckk. Seconds later my cheeks touched the table surface and for the first time ever my ass felt full. I didn't even move for a couple of minutes, I just sat and enjoyed the fullness in my hole, feeling the cock press into new areas my fingers had been unable to access. I shifted my weight and picked myself up a couple of inches and dropped myself onto it again... oh my god. Soon I was picking the pace up, raising and lowering myself onto the cock trying different speeds and angles of attack, but the best one was always pulling off until just the head was gripped tightly by my well lubed ass and slamming my ass back down to take the full length while my own cock strained and bounced in front of me.

I must have enjoyed this for 30 minutes before the pressure in my balls became too much and I squirted all over the floor in front of me. I sat back down on the dildo one last time and looked down at my own cock as it slowly went limp again, cum still dripping down its length. I hadn't planned this part at all but in a quick motion I scooped up the cum from the end of my cock with my finger and brought to my mouth. The taste while not delicious, was not disgusting either, certainly not as bad as girls seemed to make out so I licked my finger clean and savoured the warm saltiness of my man juices for the first time.

I let myself catch my breath and when I finally went to move I almost forgot I still had the 7" of purple pleasure inside me as it slid out with a satisfying pop. I was familiar with my own ass juices having had my fingers coated in them many times now, but seeing them coating that cock was so satisfying. Composing myself I cleaned up and hid the dildo away at the back of a drawer, knowing full well that it wouldn't stay there for long before being required again.

My horizons widened over the next few weeks, and another turning turning point came when I realised that when I was watching porn I was becoming more fixated on the dicks than the girls. If a girl was on her knees worshipping a cock, then I imagined myself in that situation instead of her and would mimic her movements with my dildo. If the girl was on her knees with her ass arched in the air with a cock pumping in and out of her ass, then I imagined myself as her and would assume the doggy position and slide the dildo in and out of my ass trying to match the pace and rhythm of the scene in front of me. This new conclusion of mine led me to the categories of Crossdressers and eventually... Gay: Guys dressed as girls that could have fooled anyone after a few drinks; some less convincing attempts but nonetheless appealing as they simply dressed in slutty outfits while they performed some lewd acts; or the guy on guy scenes where there was usually a more dominant top and his younger sub bottom in jock straps or leather harnesses.

I decided I needed to order a few more things to continue to spice up my solo sex life: two jock straps, (one red satin material, and one black with a mesh pouch); a wet look harness; a butt plug; some suspenders and short a short schoolgirl skirt; and a new dildo. While my 7" friend was good, I needed something more now. I figured while 10" was probably too much for my ass to take anyway, it would at least give me plenty to grip onto as I fucked myself harder and harder, plus a little extra girth couldn't hurt. Of course I also did some trimming downstairs and used hair removal cream on my ass and balls, and trimmed my pubes back to nothing more than short stubble.

Over the next 3 or 4 months I started to build quite a respectable collection of sexy clothes and toys. I loved the jock straps and the comfort they offered while I rode my dildos while containing my own cock at the front, and I could see why all those young slutty bottoms wore them for their lucky, hot daddy types in the videos I was watching all too often. And if I felt extra naughty, I would pull on my white suspenders and panties and play with my cock and ass beneath the tiny tartan schoolgirl skirt.

Sometimes to give myself that extra tease, I would insert the butt plug and venture out into public, occasionally with my slutty outfit on beneath my everyday clothes. Wondering around with my ass stretched and stuffed and my jock strap poking out above the waist of my jeans would work me into a frenzy. I wondered if anyone noticed? Maybe I wanted someone to notice how much of a horny young boy I was? Sometimes a well built older guy would catch my attention and my eyes would instinctively drift to his crotch imaging what type of cock he was hiding. But I would never last long outside before I had to rush back and bring myself off again.

The next thing that happened was I found myself signing up to a Guys and CD meeting/chat site. In about 20 minutes I'd made a quick profile and included a short description of myself: 'Young horny bottom boy who likes ass play'. I added a few other preferences and dislikes and had to select who I would be interested in meeting (guys, couples, CDs) even though the idea of actually meeting someone seemed like a far out fantasy. I uploaded a quick photo of myself, bent over on my bed in my black mesh jock strap with both dildos just in view, (thought I would be a bit naughty!), and looking at some of the other photos people shared on their profile for the world to see, I felt like mine was definitely more conservative than most.

To begin with the thrill was just having a profile on a site like this, a site where it was clearly very straightforward to arrange hook-ups or chat to like-minded people. I enjoyed browsing the talent as if browsing for clothes online, scrolling through their pictures and reading stories of their previous hook-ups, often using them as fuel for my toy sessions. I certainly wasn't an active member on the site by any means but would be logged on a couple times a day at least to see if there was any new meat. Occasionally guys would send me private messages: "Hi" or "How are you?", or "nice pic", or simply "meet?" These were probably the most common and gained no attention from myself in return other than replying with a simple "Thanks x" if they complimented my profile or pictures.

Things changed very quickly however when I logged on one Friday afternoon and seen I had a new message from DadTop72:

"Good morning, how are you? Have you got any weekend plans? The photo of you with your ass spread showing off your anal plug caught my eye and reading your profile it seems like you are just my type. I am into younger more submissive guys with smooth slim bodies like yourself. It also looks like you are into older gentlemen? I have lots of experience and have helped young boys live out many a fantasy. Let me know if you want to chat."

"Well at leat he has put some effort into his message," I thought while wasting no time in checking out his profile to see if he had photos... "jackpot, he does...! And lots of them too!" After reading his profile which described himself as a 47 year old top into various kinks and fetishes, (role-play, dress-up, dom/sub, bondage, group fun, oral, anal, toys to name the highlights), I came across his photos (not literally at this time). His profile boasted he had a 8" uncut thick cock, and while his profile was modest, his cock was magnificent.

His cock was certainly 8" at least and could quite easily have been thicker than my 10" dildo. The head was a true mushroom head protruding from his stretched back foreskin, and was certainly the most impressive part of his cock. It looked made to be stuffed inside somewhere and not come out, the tapered tip designed to penetrate any hole and the wide base to lock itself in so it would not slide back out easily during even the roughest of pounding. His photos showed his tool from a variety of angles in different settings: shower; bed; car; bulging through jeans; sticking out of boxer shorts; dripping in cum; and also wedged delightfully between the smooth, tight cheeks of someone who I assumed to be a previous hook-up of his. I replied:

"Hello, I am good thank you, how are you? No plans for the weekend, probably just stay in myself. You? I am loving your pictures by the way. Your profile does tick a lot of my boxes." Not wanting to give away just how excited his photos and interest made me, I left it at that. A couple of minutes later his reply flashed into the corner of my screen.

"I am doing well thank you, although I have had a long week and could definitely do with some relief in the next couple of days. Would you be interested in meeting with me for some 1-on-1 fun?" Straight to the point,and he did not mess about. I was slightly taken aback by his forwardness but also turned on by his confidence. Although I had slightly hoped we would maybe just flirt and chat about what we would like to do to each other but not physically meet and execute the lewd fantasies filling my head. Before replying I looked back through his photos and lingered all to long on a photo of his cock at full length and hardness with a pearl of pre-cum shining on the tip. My mouth was literally watering as I imagined swallowing his big mushroom tip and sliding my tongue back and forth across his slit to get the taste of his pre sex juices. I replied...

"Maybe I could help with your relief? Did you have anything in mind?" I tried to be suggestive but yet leave the ball in his side of the court. I guess this was me naturally fulfilling my submissive role to an older man, just like in the fantasies I had imagined or lived out through porn.

It would only have been 30 seconds before he replied this time: "I'd love for you to come over to mine and spread your ass cheeks and replace that plug with my cock before feeding you my week-long-load. Have you ever met someone before?" Damn. I didn't want him to know I was still a true gay virgin and would have rather pretended I had experience and kept the messages going back and forth a bit longer. This was usually the time I would chicken out... but something was different and before I knew it I was typing:

"Mmm that does sound good, I was actually just imagining suckling that hard cock and tasting you, and I could do with a change from my dildo. But I've never tasted a real cock before, have you got much experience?" I knew he had experience, the comments left by other members on the site attached to his profile confirmed this:

younglad19: "What a cock! Made me cum twice, definitely meet again."

sexybttmplayer: "i have just met DadTop72. Very sexy guy, knows what he wants and is not afraid to take it! My ass is still sore. What a fuck!"

coupleofguys: "both us went round to his again for round 3 and Daddy treated us like the sluts we are. He came in both our asses and left us begging for more again. Thank you xxx!"

Those 3 comments were all left in the last month so he obviously had a pedigree, and one I was increasingly liking the sound of. There were 20+ comments from longer ago but I didn't get to them.

The next series of messages back and forth was more like a question and answer session where he would quiz me on what I would and wouldn't do and as part of my replies I would try and engage him to divulge details in how he would do the things I said yes to. When he asked if I would deep-throat him I said I would try, and he explicitly told me how he would push me to my knees and grab the back of my head and skull-fuck me. When he asked if I would like to be restrained and I said I probably didn't need to be but would give it a go, he told me in great detail about how he would spread my ankles on the bed and tie my hands behind my back leaving my ass fully exposed for him to fuck anyway he likes. When he asked if I would spit or swallow I simply said, 'swallow' and his only response was 'good boy', which sent a shiver down my back to the tip of my cock.

I knew my mind was made up when I had stared longingly at the tip of his cock and imagined how good it would taste, but eventually he asked if we were done talking and if I was ready to submit? I was nervous, but I was ready. A couple messages later and we had agreed I would go to his apartment at 8pm, and was to wear my jock strap and wet-look harness. It turns out he only stayed 10 minutes drive from me and then I suddenly realised that I had maybe passed him in the street, or stood in front of him in the queue at the shop, (and if I had stood in front of him the idea that he had been silently admiring my ass gave me a small thrill). I realised I had no idea what he actually looked like above the neck, and he had no idea about me either. But from the his photos I could tell he was in reasonable shape, quite well built and probably quite strong as well. He had light hair on his chest, and his pubes were neatly trimmed to just longer than stubble. Ultimately I didn't really care what he looked like by now, I needed to feel that cock and he needed to feel my ass and that's all that mattered.