Straight to Bottom

This is a true account of how I lost my anal virginity.

I travel a fair amount for work and a few months back I was in another city for an industry conference simply to have a presence there for my company and network with potential clients.

The last night there is the fundraising gala, which is not my favourite thing, but great food and liquored up prospects can at least make the night entertaining.

At one point I find myself standing next to the bar watching the UFC fights on the TV screen and an older gentleman I don't know comes next to me asking for an update on the previous fight.

I come to learn his name is Steve, he is a 60 year old, fit silver fox with grey hair and a grey beard, dressed to kill in his tuxedo. Myself, I am a 35 year old straight man that is pretty well built at 6' tall and 180 lbs, shaved head, blue eyes and blonde beard with no intentions of anything but watching the fights and enjoying a good night sleep before flying home the next day.

Steve and I strike up a pretty good conversation around UFC, baseball, business and married life; both of us have been with our wives for a long time and both relay being happily married at that.

About 45-minutes into our conversation, I hear a loud cheer coming from directly behind us, which I naturally turned all the away around to my left to see what the commotion was.

There were a group of people cheering a big play from the Lakers, but I no longer cared, because inadvertently as I turned, my right hand landed right on Steve's dick, my hand wide-open. I had a full hand wrapped around it and I froze.

I don't know why I didn't immediately pull it back, but I know my mouth was agape as I was absolutely amazed at how large it felt - I was in awe.

Now, I have always been a very masculine guy - I shared in my previous story my first gay experience was only a few months prior to this and that wasn't anything I sought after, but something about the sheer girth of his manhood had my undivided attention.

We look each other right in the eyes, Steve hasn't flinched either and has a small smirk on his face when I finally yank my hand back and start trying to stammer my way through an apology, no words really making sense.

Steve calmly reaches into the breast pocket of his tuxedo jacket, pulls out some cash and throws it on the bar table to cover our tabs and simply says "Come with me."

I wasn't even trying to process anything, my body felt like it was on auto-pilot and we just walked right out of the room, through the convention area and down the hallway of the hotel.

We climbed one flight of stairs with me following him in tow, which is when I really took notice to the firmness of his body; his broad shoulders, strong back and tight butt. Why was I noticing this?

I follow him right to his hotel room and we walk into the hallway of his room where we are both standing, now facing each other.

"I think you liked grabbing my dick, didn't you?" he says looking right into my eyes.

I tried to answer, but couldn't find the words "No, no, no, it was just an accident, I swear."

He doesn't break eye contact when he says "You want to see it don't you? Tell me you want to see how big it is."

My mouth opened, but words didn't come out, I just slightly shook my head no.

"It's OK if you do. I have a really big dick and I wouldn't mind showing it to you. You want to see how big it is?" he asks.

Again, no words and less head shaking than before.

Steve grabs the bulge around his crotch and says "Tell me you want to see my cock."

I take a long pause and a deep breath to quietly say "Yes."

"Then tell me" he says.

My heart is racing, but I reply "I want to see you cock."

He smiled as he replied "Good, because I want to show you, but you need to follow my rules and listen to every command I say, do you understand?"

"Yes" is all I could say feeling my head spinning unable to process everything that is happening.

"That's yes sir to you."

"Yes sir" I quickly correct myself.

"Good boy. Now take off your clothes and get on your knees" he commands as he begins disrobing himself.

My hands are shaking as I pull off my jacket and start unbuttoning my shirt. We are watching each other undress and I can hardly breathe. As I pull off my pants and underwear, now completely naked; following his command I get down on my knees. I can feel my heart beating throughout my entire body. I can't even think.

He pulls off his underwear and I see the largest cock I have ever seen in my life dangling between his legs. It must have been 9" long and so incredibly thick and a large set of balls hanging behind them.

"Crawl" he orders.

I don't hesitate and begin to crawl naked on my hands and knees across the carpeted floor, stopping when I am face to face with the monster hanging between his legs.

I reach up and gently grab his shaft in my one hand and then two, just to feel it's impressive weight while moving it around before moving to his balls, softly touching the skin and gently rubbing each one in the palm of my hands.

I am sitting on the back of my legs, one hand playing with his balls, the other now softly stroking his hardening dick and I look up at him as he still has that confident smirk on his face.

I don't break eye contact and I sit up a bit more, stick out my tongue and begin doing circles around the head when he groans in approval. I keep licking, going up one side, down the other, all the way from the tip, down the bottom of his shaft and then to his balls, making him draw in a hard breath as his dick is now hard and sticking straight out in all it's vein-filled beauty.

I give him a couple more jerks and then open my mouth and take in the head of his cock, which nearly fills my mouth on it's own, I work my way down the shaft as well, but don't make a ton of progress.

Holding it in my mouth, I do swirls with my tongue, but every time I try to get deep, I gag.

After a few minutes of this, my jaw is hurting, but I am really enjoying myself.

Steve grabs me by each of my arms and lifts me up, steps behind me and easily throws me on the bed face down.

He walks over to his suitcase and reaches in for a bottle of lube; thank goodness.

I watch him as he pours a bunch over his throbbing cock, which looks even more incredible now that it is all shiny. As he comes back to me, he drips more liquid onto his fingers and begins to gently rub up and down the crack of my ass sending chills through my body.

He plays with my balls a little bit, giving them a gentle tug, works his way back up my crack, to the top and back down, stopping on my hole, where he begins to apply some more pressure and rub in small circles.

Slipping one finger in easily, he proceeds to probe me a few times before adding a second finger, making me moan.

He is going slow, curling his fingers inside me which makes my toes curl.

Steve pulls his fingers out of me and climbs on to the bed grabbing me by my waist on both sides and I soon feel the unmistakable warmth of the giant head of his cock pressing against my asshole.

I take a deep breath in and he pushes forward softly. Oh my God it felt so good! I was so scared it was going to be excruciatingly painful, but it wasn't. He stayed still for over a minute, letting my body adjust and as he felt me begin to slightly wiggle my butt, he began to push in a little further.

He was slow, caring and patient. Worked his way a little deeper and then slowly went back to the tip and then inching deeper again until eventually he was all the way inside me, completely filling me up and again he just held it there.

He slowly pulled back and all the way out, almost making a popping sound as it came out and then put it right back in. The feeling of his cock head coming in and out of me was almost more than I could bear, I thought I was going to pass out.

Steve began to thrust the entire length of his cock inside me, picking up the pace from before, wrapping one of his muscular arms all the way around my stomach as he did.

He then leaned back and slapped my ass cheek, another new sensation for me, but I liked it. He began grabbing both cheeks and in a circular motion spread them.

Then he reached forward grabbing one of my wrists and then the other, pulling both arms behind me and pulling me more upright towards him. Holding me in this position changed the angle of his cock and he began thrusting longer strokes until he was almost out of me and then all the way back in.

As he continued thrusting his giant cock against my prostate, he hooks both of my elbows with one of his arms and puts his free hand around my neck. At this point I felt a tingling sensation and an incredible amount of cum started spilling out of me that I let out with a groan.

He pushes my head back into the mattress, grabs me again by the hips and picks up his pace.

After a few more thrusts he suddenly pulls out and I now feel empty. He flips me over and straddles my stomach holding his dick and then with only a few strokes he erupts; covering me in his warm cum on my chest, neck and face.

No words are spoken as he walks into the bathroom and hops into the shower.

I just laid there, feeling the warmth of his cum all over me, licking some off my lips and feeling some start to drip off. He gets out of the shower pretty quickly and comes walking back into the room as he dries off and telling me I can go shower now.

As I stand up it feels like an ocean of cum is dripping off me, so I hurry into the shower and clean off.

After I get out he told me I was spending the night in his room. This time I knew the appropriate answer was "Yes sir" and we slept naked in his bed with my head on his chest and eventually me as little spoon.

When the alarm went off in the morning he simply said "Come with me" and I followed him into the shower; this time together.

He had me lather up and wash his entire body and when I was finished I was rewarded for doing a great job by being able to suck his dick and then fucking me again in the shower.

I had to leave to get my stuff out of my room before my flight. We never exchanged numbers or knew each other's last names. That was the last time I saw Steve, but I will definitely never forget him.