I have a mental list in my mind of "men to do" and Tommy Sheldon heads that list. I knew Tom ever since high school.
Now, If you think this is going to be just another story of me getting to finally give that dream boat stud of a star football player some head. Well, not this time.
Because Tommy certainly was not a dream stud. The fact of the matter is he not only looked liked the school nerd, he was the school nerd.
First he struggled to make barely passing grades. But his physical appearance was what caused him his biggest problems.
There were three favorite names that described him, first was "Carrot Top" because of the flaming red hair that cropped his head, then what looked like over size ears that spread out, earned him the name of "Wing Span".
To top that off, he had freckles, his two front teeth were wide and had a space between them. Put a pair of wire rimmed glasses on that body, and you have the classic "school nerd".
The name the boys used mostly when the girls were not around was " Horse Dick". The reason for that endearing name is probably most obvious to any one reading this story.
Tommy's body was flat out skinny, he was skin and bones from the neck down, when he was naked taking a shower after gym class he was a sight to see. Attached to this red haired, big eared skinny body, was a cock that hung down two third's of the way to his knobby knees.
His body had very little hair, but his huge cock seemed to explode from a patch of flaming red pubic hair.
That big cock is what made Tommy number one on my "men to do list"
I was not in Tommy's gym class, but I made a special effort to find some reason to get in the locker room and into the shower area when Tommy was there. I was absolutely fascinated by that huge uncut cock.
By the time I was in High School I knew I was attracted to boys, I knew what that meant, I was gay. I didn't want it that way, and tried my hardest to be the macho type. But I just couldn't pull it off.
You see I had my own little problem. I was naturally effeminate, I have always looked much younger than what I actually am. That makes me a "Twink" The term "Twink" was tacked on to me a little later in life. In High School I was referred to at times as "that pretty boy"
I did manage to have a few friends, one reason for that I was a star athlete in my own right, I was hot miler on the track team. This natural ability did me good when a couple of times a few of the boys decided they wanted to take my pants off and have some fun with the pretty boy.
I managed to out run them then. But I have to admit I wonder know as I reflect on those two occasions, if maybe I would have enjoyed the fun, but at the time I was very much against the idea.
I decided to make friends with Tommy, not just because I felt sorry for him, I did have an ulterior motive, I wanted to have that cock.
We did become good friends, in fact the best of friends, we even got to the point where we had a couple of jack off sessions.
I love to reminisce of that first time.
Tom's dad was in the field cultivating the corn, I had helped Tom with his barn chores that day, and after we finished we crawled up to the hay loft to take a break and the conversation as it often did turned to girls. Of course that led to getting that feeling down in the crotch, one thing led another and the next thing we knew we both had our cock's out.
The feeling I had at that time even to this day just about overwhelms me. As we were laying back in the soft hay, and talking about girls both our cock's were getting hard, and the precum was starting to ooze from them. Tommy was the first to take his cock out of his pants. I think he almost had to because even in his bib overalls, his cock was making a big tent, and even with the lose fitting overalls his cock was beginning to stretch the material. I was spell bound as he unsnapped the snaps to his fly, I was surprised at my self as I caught my self licking my lips.
He was lying back half sitting up on the hay as he fished around inside his pants and I knew he was getting a good grip on the monster that was about to raise its beautiful head.
I was not disappointed as the head came into view, he had hold of it about midway down the shaft, and the head was partly folded underneath and it suddenly broke free as it popped into view. It wasn't all as hard as I hoped but it did have that swollen look, I was captivated by the view as he adjusted the now freed monster, and made himself comfortable with his cock now free from its prison.
My cock was still in its nest, and to be honest I wasn't thinking of my cock at that moment, I was mesmerized by the shear size, and the fact I was this close to the prize I had so long fantasied about.
It seemed like I was frozen in time as I watched him start to slowly pump up and down, it didn't seem like short strokes, there was to much cock for short strokes, he slowly pumped up and down. I knew instantly this was something he knew very well how to do.
I did find out later, this was his first time with some one else present. As for me I had a couple of Jack off experiences with my two cousins, so I wasn't a virgin in that area.
He was pumping regular strokes and I could tell he was going to climax soon, he was all consumed with him self and it felt like he wasn't even aware I was there, soon the strokes picked up speed, and he looked over at me, and said, "Am I flying solo today?"
The invitation to take out my cock brought me back to reality, and I pulled out my little five incher.
Jeez Danny I've seen some small ones but that one is a prize, he added I think that's about the littlest one in the whole dam high school. At least the ones I've seen in the showers anyway.
That remark didn't make me feel to manly, it only made me feel less of the macho man I wanted to be.
That remark at that time I do believe had its effect on me that has lasted this far in my life. I think I knew deep down in my heart I was gay and no matter what I would try I knew at that moment not only was I gay, but I would be a submissive! And that fact remains true today.
After that remark I lost the momentum and my cock started to go soft, I tried hard and pumped furiously and finally attained the desired results. Tommy was at the brink and ignoring me he squeezed hard at the base of his cock, pointed it at me, and unloaded. He hit me square in the chest, when I saw him aim at me I just froze knowing full well what he was going to do.
In the jack off sessions I had with my cousins, we had never cum on any of us, we just unloaded in any direction. As I watched fascinated at the cum splattering on my T shirt, Tommy leaning back his body stretched out taught moaning in ecstasy his cock pointing straight at me, and firing in rapid succession streams of hot cum hitting its target squarely.
It was a scene that was burned into mind that remains with me to this day. Soon after Tommy finished, I managed to get a load off, but it was pitifully small in volume and intensity compared to his, but to me and what I was used to it was a gusher.
Soon after we had unloaded we left the scene, it was several month's later that we managed to get back together for another jack off session. I think Tommy got a case of the guilty feelings and just tried to ignore me.
But the time finally did come when we were back in the hayloft and ready for another session.
This time I made up my mind I was going to at least get a taste of that cock, I wanted that cock deep down in my throat so bad I was willing to take some risks. The risk here was alienating Tommy from me for ever, but I was getting ready to go to Barber college and then start looking for career opportunities and I had no idea where that would take me.
Finally I found myself up in the familiar hay loft, we both had our cock's out and both were fondling our own, I guess I had that look in my eye, Tommy must have realized it, and he just pointed his cock at me and the motion and the look in his eyes told me to take hold of it.
I did just that, the look on Tommy's face was a picture I will never forget, he told me years later that was the first time some one else had ever touched his cock. I took full advantage of the opportunity to feel and fondle my long thought after trophy.
The feel of that monster in my hand made my cock dam near shoot its load right then and there. I started to pump his cock slowly with my right hand and my left hand was doing the same thing to my own rampant cock.
Tommy's cock was not rock hard, it couldn't get rock hard. The reason being if enough blood surged into that giant to make it that hard, there would not be enough blood left in his body to sustain life.
It felt so big in my hands I panicked because I suddenly realized I might never be able to get this thing in my mouth with out hurting him with my teeth. As I was conti plating this thought I was slowing pumping it, the shear size of it dam near scared me, and I wondered if I had gotten in over my head.
I couldn't resist the opportunity to try, I slowly bent down on my knees in front of him, he knew what was about to happen.
As I reflect back on this moment, I think he had a moment of guilt, because he started to pull back, I still had hold of his cock and pulled it toward me while my mouth was salivating, I first wanted to lick the slit and head, Tommy was resisting just a little, but I kept the pressure on pulling it forward.
My lips were about to touch my prize. When a chilling shout came from the barn door, Tommy's Dad was there yelling for Tommy. It was panic time as we both fumbled in terror, me to get my cock back in my pants, and Tommy had to pull on his Bid overalls up, in a hell of hurry.
His Dad got suspicious right a way, as we both with no doubt very guilty looks climbed down from the loft. I think his Dad figured we had been jacking off, and no doubt knew we were just being boys, and doing what boys do at times. I don't think his Dad ever knew just how close his son was to getting his first blow job.
His Dad promptly sent me scooting out of there, and I headed home, only to stop on the way and reflect on the recent experience. And of course had to jack off to settle my nerves down.
As I think back on it now, there is no doubt in my mind, If I would have tried to suck that monster at that time I would have botched the job badly.
I know that because when I finally did get to suck that cock I had a lot more experience at sucking cock, and especially big cock's, and it took every bit of my experience to get the job done.
In between time of that near miss and actually getting to do Tommy, I need to tell you a couple of major things in my life.
First of all I realized at the moment I knelt in front of that huge cock, I probably would not be able to get it in my mouth, certainly not all of, it was just to thick and to dam long, I would never be able to get it in with out scraping it with my teeth. And I had sucked one guy with a long dick before this and I knew I would gag. So at that point I knew I would have done a poor job.
I was not about to give up on it, it only made my resolve even stronger, and decided if and when I did get that chance, I would be able to handle it, and do it well.
I put my self in a training program. At first I got a eight inch dildo and worked on that till I could get it all the way down with out gagging. I got the thickest one I could find because I knew Tommy's was so dam thick I would be scraping it with my teeth.
As it turned out that would become no problem. But more on that later.
I worked my way up to a ten incher, even attaching it to a wall at kneeling height just so I would be in the right position when taking it all in.
That practice did me well, as I decided that although I would suck as many cock's as I could, I would try and specialize in big cock's.
I did stretching exercises with my mouth and worked hard to relax my throat to get rid of the gagging reflex.
This program worked out well, as I had a couple of opportunities in Barber college to put it into practice.
During my time at Barber College one night three other guys and myself were cruising around town we had a few beers and decided to go to a remote area where I was going to give each of them a blow job, it wouldn't be the first time. These guys did not consider themselves gay.
But this particular class did not have any women in it, and guys being guys they all had active cock's. I was always around and available, so I took good care of my buddies.
It turned out to be a few beers to many and a terrible crash ensued, One death, Billy, Tim and me were badly injured. I got it in the face, and had a broken jaw in two places, to make a long story short I ended up with all of my teeth being extracted and I got dentures.
It's a good and bad thing having dentures. I won't go into the problems with dentures here.
Now I have to tell you if you like to suck cock, the ability to remove your teeth is a God send. If you are on the receiving end of that blow job, I am told it is an experience beyond words.
After the healing process I returned to finish out my classes and had a few chances to take care of another couple of buddies.
It was during my internship that I got a chance to do a really big cock that would put my training program to the test.
He was a Latino guy, and not to bad looking. I won't go into how we got together.
But I ended up kneeling in front of this guy, his pants down and standing in front of me, and I found my self staring at this beautiful long cut cock pointed right at me.
I knew instantly here was what I had been looking for, for the past three years.
It wasn't very thick, not exactly a pencil dick, but it was long, thin, and hard with a very slight downward curve even when hard.
I remember the look of surprise on his face, when I took out my teeth, and placed them in a plastic bag I always carried for just that purpose.
Remembering to breath through my nose I started to take his cock slowly, very slowly, forcing my throat muscles to relax against the invader, controlling my breathing, forcing my throat to relax, and enjoying the taste his cock. I had been in such a hurry to get his cock in my mouth, I hadn't even done any licking of the cock head or balls. I just grabbed a mouth full and started absorbing him in side my mouth.
I tightened my toothless gums around his cock, and slowly at first started the pumping motion, he instantly went into ecstasy. I hardly had a chance to get down to the enjoyment of the moment and he stiffened, the slight downward curve was working to my advantage and I had his long cock all the way in, I felt the tickle of his pubic hairs on my lips, I was actually deep throating a real cock, I was ecstatic at this revelation.
But it was short lived, as he exploded, my first deep throat experience, the first time a guy had cum so deep inside me. I to unloaded at that point.
We got together a couple of times after that, before my internship ended.
I will skip over about four years here, and just say I ended up on the west coast, and just inherited a upscale shop from the man that owned it. He died suddenly from a heart attack, and left the shop to me.
Just to keep the record straight, he was happily married for twenty three years, but I was a good diversion for him, as his wife refused oral sex. My extra talent gave him much pleasure, and I did him a couple of times a week.
I did have several experiences on the west coast, one affair that lasted about nine months, several one night stands. And many glory hole experiences, those experiences gave me a couple of big cock experiences too.
By the time I was ready to take over the shop, and while the legal process was in the mill, I decided to make a trip back home.
Needless to say, "doing Tommy Sheldon" was at the top of my list of priority's.
To keep this as short as possible I won't go into detail as how we got together, but a few things do need to be mentioned here.
The first time I saw Tommy walking down the street I didn't even recognize him, I passed him right on by, it was him that recognized me. The cowboy hat, the wrangler jeans, and cowboy boots through me for a loop. When I finally did recognize him I was stunned. But all I had to do was look down those tight wranglers, and the bulge looked like a grapefruit in his crotch.
We had a couple of beers together, and I found they had a barn fire and it burned to the ground. That was shock to Tommy's father and a three months later he had a fatal heart attack.
The insurance money went to his mother, and the two of them turned the old run down farm into a land mark. They built a beautiful new barn, took to boarding horses for the folks that could afford it, and a riding stable. The business flourished, and Tommy was at last riding high.
When he asked me if I would like to see the old place and what he and his Mom had done to it. I didn't need that grapefruit bulge in his wranglers to remind me where my priorities were, the mental image of that big cock at eye level was still as fresh in my mind as if it had been yesterday.
As we started the drive to the farm the conversation turned to small talk, and he told me he has a regular girl in town who often times needs a little extra spending money, and she takes Tommy on. He laughed because she says she has to be sure she has the next day off from her regular job because she tends to walk funny the next day.
I found out the girl was my sisters best friend.
He showed me around, and I was impressed as to the building, the cleanliness and the workmanship of the building.
When we got to the tack room, the smell of leather was overpowering, and I think I swooned. It didn't take long for me to catch on this was Tommy's favorite room too.
The tack rom was impressive, bridles, riding crops, harnesses of varying designs. Several saddles were lined up against the wall, sitting on saw horses.
His mood changed too, and he became little bolder, and mentioned about the times we had in the old hay loft. Well one thing led to another. He said right out the last time we were in the loft he knew I wanted to suck his cock. He also said he never had good blow job, in fact he actually never had a blow job.
Every time Cindy ( the girl in town ) tried she just couldn't get her mouth around his cock, and when she tried, her teeth hurt like hell. He never did get a real blow job.
I decided to tell him I was gay, and when I did he started laughing hard and loud. Finally he said "Shit Almighty Danny" you think I didn't know that!
When he stopped laughing, I told him if he really wanted a good honest to goodness hot blow job, now was his chance.
He laughed again and said "shit Danny", I thought you would never ask.
About that point, I was surprised to fined Tommy getting a little assertive, he leaned against a saddle hanging on one the saw horses, and motioned for me get into position. I was instantly on my knees, he told me to take his pants down. First unhooking the big western style belt buckle, unsnapping the top button, and unsnapping the buttons on the way down, and after each button pulling the flap to one side.
Finally all buttons undone, I started pulling the wranglers down, that wasn't easy as they fit a little tight, his boxers were coming down too, his cock already beginning to swell didn't make the job any easier. When I finally got the pants down to his ankles, the boxers were part way down too. The swelling cock pushing what material remained outward.
As I reached for the waist band of the boxers, the monsters head popped out of the fly. I had to unbutton the boxers to get them down.
He asked then, Well Danny boy, you think you can handle that thing? No problem I managed to squeak out, my mouth watering to the point where it was dripping down my chin.
He started to explain he didn't think my mouth was big enough to get it in, with out scraping the living shit out it with my teeth.
Well now Tommy "old buddy" I said, I just happen to have a secret weapon that will make that a "no problem".
I reached in my back pocket and pulled out zip lock bag and showed it to him. He got a puzzled look on his face, and said, now what the fuck is that supposed to mean, a plastic bag? Yeppers I said.
I then I removed my dentures, and Tommy said, holy shit buddy! That just might work at that.
About that time I stood up and said Buddy, I got to get my dick out too, he said ok, but I have to tell you right here and now, I ain't queer and I don't play with other guy's dicks. Not a problem I said.
Being at this point, and seeking this trophy for so long, I could hardly believe I was on my knees, ready, willing, and able to take my prize.
I thought I knew what a hunter felt as the cross hairs of his scope centered on the trophy he had been looking for all his life.
My right hand had the cock at its base, I was sensitive of every little detail, I even felt the pubic hairs on my hand. I aimed the cock head straight at my mouth, I saw up front, up close, the enormity of the red blood swollen cock head, the skin stretched back over the enormous head.
I have to admit at that moment I had reservations as wether or not I could do the job. That cock was so dam big, I knew I had worked hard for this very moment, and every cock I sucked up to this time was a training exercise for this very moment. Still I was flooded with doubt.
I'm a little near sighted and as I brought the head in line for me to put it in my mouth, I could see the swollen veins running back to the pubic area and crisscrossing over the expanse of the cock.
Finally sticking out my tongue I realized I was licking the slit of my dream cock, with out thinking before each move, I was licking the slit, the head, and licking all round the head and soon my tongue was sliding down the entire length of the shaft, my right hand felt like it had hold of a giant cucumber. I moved my hand so I could lick all the way down the shaft, I wanted to taste the pubic hairs, I wanted them to tickle my lips.
After several minutes of this, I could feel Tommy was getting impatient, and the time was at hand, now or never, I had to put this monster in, the test was here. I stretched my mouth as far as I could, pushed my head forward, at the same time pulling Tommy towards me, to my astonishment, I suddenly realized it was in, I actually had the head in my mouth.
I don't think I even thought about it, but when I finally became aware of what I was doing, the cock was past my lips, and was beginning its entry into my mouth.
Breathing right is important when you have a mouth full of any thing, and a big cock is no different. As my mouth was filled to the point of being air tight, through my experience I learned to breath through my nose, I was breathing so loud I could hear my self, it seemed like the whole barn and its surroundings were perfectly still, all of nature was listening to my breathing, it seemed that loud to me.
Its also necessary to take the cock slow and allow your throat muscles to get use to the intrusion, and when they are well trained they will relax and let the intruder continue, but it has to be slow.
It also necessary for me to control the cock so its owner don't get over anxious and start pushing his cock in to fast.
It seemed like I had control, Tommy wasn't fighting me, and the cock was slowly going in.
I stopped the forward motion from time to time and drew back and forth often so as to relax the muscles and give the cock the sensation of being worked on. After all it's the cock and its feeling that's important here, I'm just the tool. This action continued for several minutes, slowly taking more and more cock. The sensitivity of my lips, the gums, and my taste buds seemed to be working on overdrive, I tasted his unique taste, and felt the unique feel of his cock on my gums.
Tommy was leaning back against a saddle and groaning, finally I had to pull out if only for a moment, so as to get my breathing back, but it was only for a brief moment, and I had it back in faster than I thought possible, soon I was nearing the base, but found I had a ways to go, finally I felt the tickle of a pubic hair on my lips.
I knew I was ever so close to a life long dream, that of Tommy Sheldon's cock all way down my throat. Continuing the back and forth motion, with this huge cock down deep inside, I had to stop once again, and pull out, when I did I continued to lick the shaft giving my throat a rest at the same time.
Quickly back in and back where I left off, there was more hair and I knew I was close. The sensation of that monster down so deep inside me, I just don't have the words to explain. Unless you are able to deep throat you will never know the feeling.
Finally I hit the mark, he was all the way down, I had a mouth full of hair, and I was against the pubic area. My dreams were reaching reality. Now all I had to do was get him to cum. Unfortunately that came all to soon, the gums had done their magic, the soft lips, the motion, his first blow job, and he exploded with such force and volume I gagged, and almost pulled off, but I caught my self, and with shear will power and experience I stayed on, and took the full load.
I lingered on the cock as long as I could, and wondered what Tommy was feeling. Later he told me it was the greatest sensation he ever had. He said when he looked down at me, I looked liked I had been impaled on his cock, he said he half expected to see his cock come out the back of my neck.
After the initial orgasm subsided, I clamped down on his cock with my gums. Here is where the bare gums does a fantastic job. The hard soft gums giving a sensation to the cock that can never be attained any other way. I slowly drew back toward the head, squeezing the remaining cum to the head, then I would put my lips on the head and take as big a suction as I could so as to get every last drop of the precious cum.
I just kept sucking the head, sliding the cock in and out of my mouth, licking the entire shaft, even sucking on the pubic hairs, I just couldn't get enough of that cock. I kept it up till Tommy said, we got to let it go for now, and he pulled away.
All good things have to come to an end, and so was the end of me doing Tommy Sheldon for the first time.
I did him three more times before I headed back to the coast. But being the owner of my shop I managed to get away a couple of times a year to come back home to visit my mother. And to do Tommy Sheldon again and again.
The last time he said he wanted to screw that pretty boy ass of mine. Well I'm thinking about that. I'm sure as hell no virgin back there, but taking that monster up my ass is something that I will have to think about.
This time its him that wants some of me. And I'm going to have to find a whole new training program to handle that end.
If you care to you can E mail at dprdon1532@yahoo.com