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MyJockStrap

A Late Starter


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...

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