Old Jack

It was the summer of 1973 and I had just finished my first year in college. I was chasing every blonde girl I met and having relative success given that I was slight of build and very young looking. Being young looking had meant that I was often accosted by middle aged, mature men, who saw me as a pretty boy. While I was often attracted to some of those men I never gave in to their advances. The truth be told, I did fantasize about some of them quite often and masturbated frequently.

Looking back I often wish I had realized just how much I was turning them on and allowed myself the pleasure of teasing them and leading them on. Oh the innocence of youth and lack of self confidence, if only things had been otherwise. I was afraid of course and things were so different back then. I was in denial about my true feelings and still believed that real sexual pleasure lay between the legs of the blonde girls whose pussies I longed to see, finger, lick and fuck.

I was confused because many times while looking at naked pictures, which now seem so tame, of these gorgeous babes, I would imagine them spreading their legs wide and opening themselves up to be pleasured, not by me of course, but by some of the gay men who had tried to pick me up, or even other men to whom I found myself attracted. The thing is too, it was not one specific type of man, but it was always older guys.

Some were fat, some were thin, some were well built and muscular, some were tall, some were short, some were very handsome, and some were down right unattractive. Some were even really tough looking, while others were quite effeminate in their mannerisms. The one thing they all had in common was a great cock, bigger than mine, thicker than mine, hairy, manly and hard enough to satisfy the girls I longed to bed.

In my fantasies the woman I longed for would do anything with the men and the men had them yelping and whimpering. It was a short step from there to me wishing I was one of those pretty girls of my fantasies who allowed some dirty old fucker, gay or straight, to seduce me in the back of a car or in his bedroom. I was such a confused and sexually inexperienced young boy and I knew I had to get laid, to prove to myself that I was not one of those "queer" guys. In those days teenage boys were merciless about all aspects of male homosexuality.

So it was then, that I began a temporary job in the Civil Service. The pay was not great but the building, on the far side of town was full of people packed in to offices which I hoped, would present me with the opportunity to get down and dirty with some little trollop, who would show me what pussy was all about. I could not have been more wrong.

I met old Jack the morning I started. Jack was the number 2 boss in my office. He was a big portly man, with a barrel chest, tall, very strong, thick grey hair and glasses. Apart from his size, the first thing I noticed about him, when introduced to him, were his lips. He had big thick lips. His face had thick fleshy skin which was full of tiny holes. When we shook hands, Jack's hand dwarfed mine in size and thickness, and his grip was powerful.

Jack was very friendly and he instructed me personally on the details of the form filling tasks I had to perform. He seemed to be a really nice guy and he asked me lots of questions about myself and my studies, sporting interests and girlfriends. I lied and told him I had a girlfriend. The girls who worked in the office were genuinely surprised at the time Jack was giving to my training. He has never done that before they would say to me. He must like you. I laughed it off by saying every body likes me.

One afternoon, about two weeks after I had started, old Jack came up to me and asked me to help take some boxes out to his car. I was pleased to help him as he had been decent to me. His car was parked at the very end of the large car park at the top of a slight incline, affording any occupant a clear view over the rest of the car park. As we were placing the boxes in the front seat it began to rain heavily. As neither of us had coats or jackets on, Jack said jump in the back or we will be soaked. I was glad to get out of the shower.

So there I was in the back seat of this big Ford sitting next to old Jack. My shirt was pretty wet and the rain showed no sign of letting up. The windows quickly began to become covered in condensation. We talked away about this and that and then, Jack steered the conversation round to my "imaginary" girlfriend. I thought I could easily fool the old duffer, so I made up a story about how long we had been together, that her hair was blond; her name was Vicky, all the usual stuff when he asked me.

"Is her pussy blonde?"

I was surprised and because I did not answer immediately Jack laughed at me.

"You don't know do you? You haven't fucked her yet, have you?"

With that he took his glasses off and set them on the back sill and in the same movement, brought his arm around me, and pressed my left arm tight against my body. My right arm was trapped between our bodies and taking my face in his free, right hand he squeezed my cheeks as he brought his thick lips to mine and planted a sloppy wet kiss on them. I tried to break away from his lips but he was too strong and powerful for me. To my utter horror I felt his tongue probing for a weak spot to force an entry in to my mouth. Being caught unaware as I was, trapped by this much bigger and stronger man, I had to open my mouth to catch my breath and his warm wet tongue was in my mouth French kissing me.

How did I feel? I wish I could say that I just pushed him off, got out of the car and ran back to the safety of the office. Alas no. While I was repulsed, at first, his long, thick, experienced tongue was expertly exploring every corner of my mouth, tongue, teeth and gums and while instinct told me this is wrong, my own cock rose up and said allo, allo. The longer the kiss went on, the more I found myself surrendering to my own pleasure and it was pleasurable. The old duffer, moved his hand from my face and travelled gently up and down the side of my chest and then on to my hips and back up across my tummy.

I wanted him to touch me. My cock was screaming at the top of its voice begging to be touched. When his hand caressed my cock through my trousers I though my cock would explode. This is wrong my brain yelled. Fuck off yelled my cock. This is wonderful. It was wonderful. When Jack unzipped my pants, undid the button and unbuckled my belt I offered no resistance. Still he held his mouth to mine. Still his tongue danced in my mouth and seemed to be tickling my tonsils.

I allowed him to slip my trousers and underpants down by lifting myself up off the seat and wriggling a little. His big hand touched my balls and I yelped into his mouth. I could only breathe through my nose. Still he leaned against me with more force as his magic fingers, tapped the shaft, of my near exploding cock, like a flutist playing a merry tune. I felt his hand encompass my shaft and using his thumb on the sensitive underside and his forefinger on the back, he pulled my foreskin all the way down, in one quick movement, revealing my knob to the world, for the first time ever, and I exploded immediately. He must have sensed my upward thrust, for in that instant he broke off his kiss and before my howls of orgasmic delight passed over my lips, the first jet of my cum, hit my face.

I yelped with each spasm until I had shot everything I had and all the while his thumb traced insistent circles, round and round the underside of my crown, helping intensify the heavenly experience of my pulsating cock. I didn't know what to think. This was not the moment for reflection. This was the best orgasm I had ever had. His hand, his big, thick, fingers, oh my God his thumb. What they had made me feel. I was exhausted, exhilarated, bewildered, ecstatic, confused, disgusted at myself, delighted with my cock. Fuck! I wanted more.

Without saying a word, Jack brought his hand to my face and wiped my cum off with his fingers. He brought his fingers to my mouth and God forgive me, I opened up and sucked my cum off of his fingers. My cock was getting hard again. I wanted him to touch me there again but did not want to ask him, did not want to admit this weakness. Jack was reading my mind and pressed his lips to mine again and his tongue probed me. I let it in. I knew he wanted to taste my cum. I wanted him to taste it. I wanted him to share it with me. How did I know this? I don't know. It was wrong but it was so right.

He touched my cock again. I yelped. His fingers first caressed, and then rolled my balls. His thumb slid up my wet shaft and pushed my foreskin back up over my cock head. It felt even better. He squeezed my cock with his hand, two or three times, quickly, in succession. I wanted to release a moan, that started in the pit of my tummy but his mouth and tongue would not allow it. It started again. I could feel it in my balls as he tickled them. I pushed against his hand as it embraced my cock. His thumb slid up and down against my cock head. My foreskin slipped down on the command of his thumb. I thrust upwards again.

The kissing stopped. I gasped for breath. My orgasm erupted. This time I yelled and moaned freely. This time he squeezed the life out of my cock. This time I threw my head back and gave his hand my cock to hold, to tease, to squeeze, to pleasure. He milked the last drop out of me. This was the best orgasm ever too. I was lost to his touch. I was lost to my rampant desire, to the feel of this man's tender caress. He pulled me to him. I yielded myself to him. I looked in to his eyes. His eyes were sparkling. He knew I wanted his kiss. He leaned towards me and licked my lips with his sticky, thick, long tongue. He licked my lips again.

Who was this dirty fucker? What was he doing to me? Why did I love this? Why was his tongue making me hard again? What was happening?

He took my left hand and placed it below his belt. He dragged my hand up and down over his cock.

"Touch me sweetie", he said. "Touch daddy's big cock".

Oh fuck, yes, I touched it through his trousers as he held my balls in his huge hand. His hand guided me up and down his cock at the pace he wanted. The more my hand slid up and down his shaft the harder my own cock became. He felt so hard, so long, so thick compared to mine.

"Unzip me sweetie, you know you want to".

Fuck, I unzipped him. I put my soft hand inside his trousers and the heat from his big dick struck me like a bolt of lightening. I had never even thought that a man's cock would be hot. I traced the length of him as he had done to me and I loved it. I mean I fucking loved it. We were kissing and touching and it felt wonderful and dirty and I didn't want it to stop.

The wily old fucker, took his right hand from me and quickly undid his belt, undid the clasp, took my hand in his and forced it down inside his underpants. Holding my hand in his he brought it down, down, down, until we found his big balls. My fingers knew to tickle there as he had tickled me. His lips pulled off mine and his tongue licked my lips again. He brought my hand, my soft hand, to his shaft and I gripped it as he had done to me. I moaned as I felt it throb in my hand. God, it was so thick and warm.

"Use your thumb, sweetie", he breathed on me.

As my thumb ventured up his long shaft my own longing increased. My thumb reached the ridge of his giant purple knob. Sticky precum slid down to meet it. The slit made the downward slide easy. My thumb rode up the slit. The journey was deliberately slow. I did not want it to end. Finally my thumb mounted the crest of his big fat crown. He did the same thing to me again. I yelled the bastard's name. I came again on his thumb as I held his impressive, sticky, fat, man-sized, dick in my hand and as I spurted what little was left in my aching balls, Jack licked my lips again and again, and I wanted his sticky wet tongue all over my body.

Only five minutes had passed but in real sex time it was an eternity of first time pleasure for me. I had enjoyed, wanted, then longed for this disgusting, dirty, old fucker, to touch my cock and now I held his throbbing manhood in my little left hand. My God, I thought, feeling this old fucker's cock had made me come.

Jack put his left hand on the back of my head and pulled me downwards, towards his middle. With his right hand he dragged his trousers and undies towards his knees. I watched in disbelief as his cock was totally released from the restrictions imposed by his clothes. God he was big; bigger than the length of my hand. Sticky, wet precum flowed freely from the pee hole. I couldn't help myself. I stuck my little pinkie finger in to that wet hole. Old Jack sighed. He had a surprised look in his eyes.

Now I am nobody's fool. His hand was pushing gently on the back of my head, but there was no way I was doing that. I wanted to. I'd be a liar to say I didn't want to know what it would feel like, what it would taste like, but not today. I wasn't ready. In stead I reached upwards and I kissed his disgusting, beautiful, fat lips. I sucked his lower lip in to my mouth and as I did so I made a circle with my thumb and forefinger and slowly, almost imperceptibly, slid it up and down the cock head that sat proudly on Jack's shaft. I slurped his lower lip in to my mouth and squeezed his big, purple, bell end as gently as I could.

He moaned audibly and his breath went up my nostrils. It was warm and dry and eager and filled with desire. His hand left my head and went to my slim waist. I squeezed his shaft and slid my thumb back and forth across his knob. He moaned deeply again and my nostrils filled up with his exhaled desire. I drew my tongue across his lips as he had done to me and he sighed deeply.

His hand left my waist and sought my hip. In a moment of understanding, I leaned towards him allowing his hand to cup my buttock. I sat on his hand and we both sighed simultaneously as he squeezed my bum. I tightened my grip on his cock and pulled down hard several times.

"Again, again", he gasped, holding my bum tightly and then releasing it.

I couldn't believe it. My cock was rising. I wanted to touch myself because he was feeling my bum. I reached for and traced my fingers through the thick forest of his dark brown pubic hair. I moaned. His pubic hair was just the best. Soft, thick, the way I wanted mine to be. His hot cock was the one I should have. I let my hand love it like it was my own. I am the best at this I thought. This is my cock, I thought. I know how to do this, I thought.

Then it happened. I wanked Jack's big, thick, fat, cock, like it was my very own. I pulled my lips from his and dropped downwards. I voluntarily brought my young boy's face to his pulsating, leaking, purple, cockhead. I gripped his shaft tightly. I brought my lips level with his knob. I did it. Like a fucking dick lover, I did it. I stuck out my tongue and flicked it across the underside of his bell end.

Jack thrust forward and his cock struck itself against my lips. I could smell it. I could taste it. A thread of precum joined my lips to his slit. I licked the underside again with a long slow sideways movement of my tongue. It was in slow motion. Using just my finger and thumb like a spanner I slid them up down his shaft with a feather light touch but ever so rapidly. He thrust out and upwards.

I licked right the whole way up the slit of his cock, glided the underside of my tongue over the crown several times, increased the pressure of my finger and thumb up and down his thickening shaft and as I did so he groaned, then moaned, then whimpered, then roared and before I could get out of the way, the thickest, creamiest, longest rope of cum, shot upwards hitting my tongue, my nose, my eye, my forehead. This was followed by several more, in quick succession, as Jack roared and squirted and spasm-ed and thrust and squirted and thrust and leaked and cried out and then went quiet.

For a few seconds the silence in the car was broken only by the pitter-patter of the falling rain. I looked down at Jack's softening cock and it seemed to me to be a beautiful thing. My hand was covered in his creamy white cum and yet more was dribbling out his pee hole. This was the first time I had ever held another man's cock in my hand and in spite of my reservations and up bringing, I loved it. How could something that feels this good be considered so wrong by so many people? I just didn't understand.

Looking at Jack's purple knob, I felt an aching in my own cock that just would not go away. Jack was recovering from his noisy, sticky, orgasm and he took my hand to his mouth. He licked the cum off of the back of my hand and then began to take my fingers in to his mouth. My God his tongue really was thick and sticky wet and I thoroughly enjoyed having him suck my fingers.

Taking both my hands in his he moved us round in the seat until we were facing each other. He placed my left hand on his now soft cock and some how I knew he wanted me to squeeze the last drops of cum from him. I did so with relish and brought my hand up to his mouth again.

"No", he whispered. "Your mouth".

I made a point of letting him see me savour his cum and he took my hand in his again and twisted both my arms behind my back. Once again, I was helpless, but my cock had no such fears, standing erect, begging for attention, although it felt just a little sore also. Taking both my arms in his left hand, Jack leaned forward to kiss me again. Like a slutty woman, I surrendered my mouth eagerly to his, with wanton abandon. His tongue conveyed lots of his salty cum straight in to my mouth and as we kissed again, he caressed my aching little knob.

He knew from my upward thrusting that I was loving this attention. Using his tongue with experienced ease, he moved his cum from my mouth to his and back again. I was in cum heaven. I was loving every second of this exchange, the taste and texture of his man seed. I pictured what we were doing in my mind and it was just like one of my perverted little fantasies, only I was really doing it. I was so turned on and I felt so sexy.

Jack deposited his cum in my mouth and broke off the kiss. He took his hand from my dick and started to run his fingers and thumb up and down my throat.

"Swallow it, sweetie," he said to me. "Swallow all Jack's cum. You know you want to, don't you. Let me hear you gargle my cream and swallow".

I did it. I fucking did it. I leaned my head backward for him and letting his cream run to the back of my throat, I gargled loudly for this dirty old fucker. Not for a second or two. Oh no. Not this cock lover. No, I gargled and gargled. Twice I almost choked and little bubbles of sticky cum appeared on my lips. All the while Jack's big, thick, hand caressed my throat lovingly. Then, as he licked my lips again, with his delicious, fat, sticky tongue, I swallowed this big man's cum.

Jack still held my arms behind my back. He was looking at me now smiling. He touched my hard cock again.

"My, oh my," he said. "You really love this don't you? Do you want to come again sweetie. Does this little boy dick want Jack to put his big hand on him."

"Oh please Jack," I begged him. "Please".

"Please what?" said Jack, feigning innocence and ignorance at the same time. "What do you want sweetie? This?"

He ran his forefinger up and down my shaft, lightly. This brought a moan from me.

"Don't tease me Jack, please." I begged again, with desperation in my voice.

"Well, I will consider it, on one condition, and one condition only", came his reply.

I did not think before I answered, such was my need in that moment.

"Anything", I said in desperation. In my mind I could hear my cock saying the same thing, yes, anything.