5 comments/ 66652 views/ 6 favorites A Late Starter By: Curious67 I guess it wasn't a year after I got married I started figuring out I was looking for something more. Nothing emotional- my wife's great company- but sexually. I created a screenname she didn't know about and started surfing the Porn Sites-tame at first but I found myself exclusively bookmarking the Transexual and gay sites. After a night of drinking and the wife asleep, I put together a profile stating I was looking for an experienced guy (Preferably modestly hung;I was still a bit nervous!)and entered a local m4m chatroom. At first I was surprised, as the room was full but noone talked-then I found out why! It seems everyone did their talking in IM's,looking to hookup, and seconds after I got in room I started getting my share. Some were easy to ignore... guys looking for a dick to suck, and that being what I wanted to do, they did me no good; guys claiming to have 8 or 9 inch super thick cocks-I winced just thinking about it! However, one guy, Aron, stood out - a few years younger than me, a relatively modest 6.5 inch cock, and needing to blow a load! I couldn't get free that night, and over the next few weeks, I kept trying the m4m room, and never found anyone interesting...except Aron, and we never seemed to be online together when I could get away-Frustration! Finally, one Tuesday, my wife was going to a Buffet concert, I had the day off, and I found him. It had almost gotten to be a running joke that his first IM would be about hooking up, I'd say I couldn't get free, we'd talk about what we'd do if we could get together, then both move on. He shot me an IM that night to the effect that he REALLY needed to bust one off, and when did I think we could get together. I knew he lived close, so my reply was "You live 9 minutes away, I figure it'll take 20 seconds to open your fly, so about 9 minutes and 20 seconds after I get your address, you can be stuffing my mouth with it's first dick." His address popped up about 5 seconds after that, and I was in my car, and sure enough in 9 minutes I was knocking on his door. My stomach was flipping-I was scared of this but wanting it at the same time-and he opened the door. I stand 6'2, 220 and can take care of myself, so when I saw him, I was a bit relieved, as I had 6 inches and 60 lbs. on him and if I started hating this I figured there outta be no problem getting away. I didn't want to give myself a chance to back outta this, so I just said "Aron?". He smiled and said "Hey Joe." as I walked in. I went straight to his couch, sat down and crooked my finger at him in the classic 'C'Mere' gesture. He walked over and stood in front of me, the lines of his cock evident through his jeans. I didn't even stop to think, I just reached up and started undoing his belt with hands that trembled visibly. He didn't push or say a word, just looked down with a smile at this big guy shaking like a teenager on her first car date. I finally fumbled his pants down, and saw a tiny wet spot in his underwear at the end of a tool straining against fabric. A deep breath, I hooked the elastic down under his balls, and stared. I was face to face with the first erect cock I'd ever seen, and was in awe. The head was sort of heart shaped and purpleish, the shaft more red tinged with veins standing out on it like Mr. America's arms. My deep intake of breath rewarded me with a scent of his manhood-so different than a woman's crotch and SO mysterious and exciting. My misgivings disappeared in that scent, and I gently pushed his dick up flat against him and ran my tongue from his balls to the base of the head and back down. I may not have done this before but I've gotten alot of good head and drew on that experience to work on Aron's shaft. I worked my tongue around the head, starting at the bottom and circling up to the tip, where I got my first taste of cum; I was getting to him and the eye of his prick was weeping openly. Salty, a smell vaguely like bleach, it wasn't bad at all and I found myself looking forward to him shooting in my mouth...I was eager for it in fact. I opened my mouth wide, and covering my top teeth with my lips, my bottom teeth with my tongue, I took the entire plum into my mouth, earning me a sigh from Aron. Marveling at the softness of something that was still so hard, I popped the head in and out of my mouth, amused by the sound it made each time. Aron obviously enjoyed this as I felt his cock swell fractionally larger, and he moved for the first time since standing in front of me. His hands slid behind my head and gently but firmly began pulling me into his groin, more and more cock sliding into my mouth each time. I hit a point where I felt my gag reflex kicking in, and I hastily wrapped my hand around his shaft, so only as much cock as I could take without throwing up would go down my throat till my hand hit my lips and stopped the thrust. We stayed like this for a while, Aron gently fucking my mouth, holding my head, me loving the feeling of being used. Aron stopped, suggested we move to the couch so I could 'get a better angle', and I told him sure. I hadn’t expected him to strip before lying down, but figured I should too and took my clothes off as well. Aron murmured "Nice cock" and motioned for me to get above him in the '69' position and I did, going down on him again, admitting to myself that this angle made sucking him easier, and the blowjob he started giving made me decide this was a VERY good idea! I was straddling his head, and this spread my asscheeks somewhat, and I felt a fingertip beginning to rub in circles on my slightly opened hole. Aron had gotten some lube on his finger, and was spreading it generously on my hole, increasing the pressure until the tip pushed in, then waiting for my reaction. WOW, it felt good, and I reflexively gulped a huge gasp of air, forgetting the cock in my mouth, so I took him much deeper and with much more force than I'd been able to manage earlier. I guess I was so focused on that finger that I forgot to gag, and Aron was obviously reassured by this response, as soon the finger was fully inside me, stretching and exploring, then withdrawn, more lube and a second finger joined it. I was alternating between focusing on the feelings my ass was experiencing and returning my attention to that beautiful cock. I gave him ferocious head as a way to thank him for being considerate enough to use ample lube and take almost all the pain out of my first anal intrusion. I had convinced myself that I was ready to give myself to this man, let him bury himself fully inside my ass and use me for his pleasure. I had come here with the idea of simply blowing him, and he'd deftly convinced me I had to give him my ass cherry or regret it forever. This conclusion came just in time, as Aron told me in husky voice to get up. He pulled the couch out, told me to fold myself over the back of it- my face down where you'd normally sit, my ass poked out over the back of the couch, my legs angled back, tip toes barely touching the floor. He explained this was the best angle for me to take my first cock, and would cause me the least pain, and since he was right the last time about angles I believed him. He was behind me and between my legs, alternately slathering his cock with lube and slicking my ass, as I realized there was almost no easy way to get up out of this position. With minimal pressure on my back, Aron could easily keep me in this position as long as he wanted. I realized my size meant nothing, and I was completely at his mercy. I surppressed a shudder-he'd been so understanding earlier, I was sure my powerlessness was just a by product of getting the perfect angle- certainly he didn't have any other reason for this position. All this raced through my mind as I felt my rectum kissing the very tip of his throbbing prick, and the hand not guiding his cock to my asshole came down to rest gently but firmly on the small of my back... (To be Cont.) A Late Starter Ch. 02 Misgivings shot through me as I folded helplessly over the couch, Aron's hand effortlessly holding me in place. My own body weight worked against me in this position- basically he could keep me from shifting as was necessary to get up off the couch with his one hand. His other hand was on his well lubed cock, spiraling it against my slick, virgin ass. He wasn't shoving, but each rotation it went a little deeper, wallowing the outside of my asshole but not straining the tight ring of muscle that would be the cause of any pain I'd feel. I started believing in his gentleness again, that flash of surrender I'd felt when I'd wanted to accept him wholly; allow him to take me for his own pleasure while easing me into this new experience in easy stages I could handle. His words were an echo to my thoughts. Never ceasing his massage of my tight hole, he leaned forward a bit (Not removing that controlling hand on my back, the still terrified part of my mind reported), and asked if I was still sure that I wanted to do this. Against the couch's back my cock was harder than I could ever remember- the skin stretched so tight it hurt- and I was feeling things from my asshole I never had before. I heard my voice, shaky and a little scared, saying, "Yeah... just...take it easy at first, OK?". The pressure from his prick on my ass ring increased a bit- not enough to force itself in but enough so that my muscles were forced to tighten to keep the invader out. "Alright, I need you to try to relax for me then. This is going to hurt at first, and you might want me to stop. Will you give me 10 minutes, and if you want me to stop then, I will...?". I now know what he was saying, but at that moment I was just overcome with gratitude over his understanding. "Sure". The tip of Aron's cock started pushing hard against my rear hole. One hand, no longer needed to guide his tool, came down to grip my hipbone while that unnerving other hand on my back kept me from standing up. With all the lubricant and my current position, I was no match for THIS assault, and that purple strawberry I'd so lovingly sucked started to stretch me open. I'm pretty sure the pain started when I was stretched just past 2 fingers worth- a hard and bright circle of agony that burned white hot. I couldn't take this- I was convinced no one could. I made some kind of noise and tried to get away... and of course I couldn't. Agonizingly I was stretched wider, and I finally remembered how to make words. "STOP! YOU'RE KILLING ME!". Even as more and more of that damned ever widening head split me open, I heard Aron say "uh...You promised me 10 minutes...uh... are you welching?" I tried to catch my breath, to say fuck yes, You win, I can't take anymore, and the pain hit a new level as my screaming rectal ring snapped over the head of his cock. It wasn't much release, but the pain dropped a bit, allowing some part of my mind to remember my promise. Aron stopped pushing once the head was lodged in, to give me adjustment time, and probably time for him to enjoy my twitching anus, milking him. Had my calves, holding me on tiptoe, not decided to give out right then, I don't know what would of happened. Give out they did, however, and I sank back a full 2 inches, which meant I took 2 inches of his manhood beyond the head right up my ass. I was shocked to discover it didn't increase the pain too much, beyond a slight burning at my asshole from the friction. I started to feel a wonderful feeling of fullness, or completion, or something, just above the pain. I desperately tried to get more, but the damned position I was in- or blessed position as it forced me to get to this point- wouldn't let me. Aron, as usual, was ahead of me and started a slow yet unstoppable push that ceased only when his balls made him stop. The pain was still there, but now I was willing to take it for the fullness I felt, and I groaned something like "God yessss ". He had me and he knew it, and started pulling that incredible cock out of me like a King pulling a sword from a stone, leaving me incomplete and empty. He stopped mercifully at the crown of the head, and sawed that slickened saber back in with an easy strong stroke that snapped my head back. It's a blur after that- the quickening pace, the mix of pain and pleasure. I'm sure it was Aron that changed the tableau, as I found myself on my back on the couch with my legs wrapped around his waist as he pounded out the end of our night. The pain never really stopped, but drifted into the background as he tattooed something in my ass, making my cock throb in time to his thrusts. I finally couldn't take it and reached down for my cock, and after two quick strokes exploded all over my stomach. My asshole cinched tight as I came, and it was too much for Aron. He went up on his arms and went stiff, and though I didn't think it possible, that miracle cock swelled larger inside me as he shot the load my mouth had looked forward to earlier up my aching but eager ass.... I didn't mind a bit. I have this fantasy frequently, and will soon make it come true. Your comments and suggestions are certainly welcome.