A Night to Remember

This is based on a true story which happened to me in November of 2009...up until this point, I had been with several old men, but this particular one was special and I still remember every detail...

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My name is Jeet...back in 2009, I was 23 years old, out of college and starting nursing school. I enjoyed my time and was living in the moment. I had one serious girlfriend in college, but we broke up soon after. I was young and adventurous. Part of that adventure was sexual. I had been attracted to old men (especially the overweight, seemingly unattractive ones) for quite some time, but it was not until college and living away from home for the first time in my life, that I was able to act upon this desire. I signed up for the usual dating profiles and hooked up with a few old men. I had some great experiences, but now I was back home again living with my parents and that burning desire to find another old man hit me hard.

I found another website, and in May of 2009, I created a profile. At first, I got a few hits. There were no pictures of myself on the website, but my profile was alluring nonetheless. One day, I received an e-mail...it was from a 56 year old man named Roger (real name concealed). He described himself as large and hairy and he also noted that he was interested in meeting me. He requested some pictures of mine. Included in his e-mail were his pictures...my heart started racing as I gazed at what appeared to be a massive bear of a man...his back completely covered in thick silver hair, his head balding on top. His lips looked thick and kissable, and he had glasses. He seemed like a gentle giant. He stated that he was about 6'2" and over 350 lbs. I was very protective of my privacy, so I never shared my pictures, but with him, I could not hold back. Nervous yet excited, I sent him a couple of my pictures.

I'm pretty modest, but girls generally think I'm good looking, and every man I had ever slept with was quite pleased with my face and body. I'm East Indian in origin, but I am relatively light skinned with an olive complexion. I run 3 miles a day and at the time I was around 170 lbs on a 5'10" body. I also lifted weights regularly and was pretty well-toned. I didn't quite have a six-pack but I was flat and firm in the stomach region. I suppose Roger concurred with the others and remarked at how handsome and attractive I was in the pictures.

We e-mailed back and forth for a few months until I was finally able to move away for some rotations. Fast forward to November 2009...I had e-mailed Roger and let him know of my plans to meet him.

In preparation, I shaved my legs and everything in between. I am naturally not very hairy to begin with, but I wanted to truly create an experience of submission.

That night I reached my new living quarters and once I settled in, I called him and we decided that I would meet at his place. I threw on some shorts (no underwear), a tanktop, and a zip-up sweater.

The drive there felt like forever. Finally, I reached, but had some difficulty getting to his actual apartment, so he stepped out to assist. I pulled up next to him and we stared at each other.

Here he was, all 6'2" 350+ pounds of bear staring down at me, stripping me naked with his eyes, fucking me, making me cum...I lost focus and my heart was going 160 bpm...I was shivering. He had a baritone voice and he looked at me and pointed to an open parking spot and told me to park there. I licked my lips and softly said "Ok". He was not able to notice that my hand was in between my legs, and that I was groping myself in excitement and also in anticipation.

I parked and stepped out. He was wearing shorts, an extra large button down shirt and shoes. He did not approach me, but I checked him out as we walked in. Once we entered the apartment, he came up to me to hug, but I pushed back and motioned that I wanted to take off my sweater first. At this point, I was wearing my tank top and shorts. He put his hand on my ass and guided me to a large sofa.

We sat down, I sat with my legs curled up but open towards him. He leaned in and asked me "How was the drive?"

I was sooo nervous I could barely answer, but I was so attracted to him. Nervously and in a tiny meek voice I responded, "Took way too long to get here."

With that, he put his left arm around my shoulder and leaned in and kissed me. We made out forever. He pushed his massive tongue into my mouth and kissed my mouth whole, wildly. His thick, meaty lips engulfed my mouth. His tongue felt like it was in the back of my throat, forcing its way in my mouth. I had never really kissed another man before, perhaps it was my relative inexperience and shame, but all my inhibitions were subdued tonight. I was going to let Roger take me, I wanted Roger to take advantage of my tiny body and ravish it till his heart was content. I had never met a man like him and he pretty much hit every mark for the man in my fantasy.

My lust for him was insatiable, but I easily could sense that he wanted me quite badly as well. He seemed to hunger for me. He seemed very experienced, but I wondered how long it had been since he had gotten any.

With his right hand, he pulled up my tank top, revealing my breasts. He looked at my nipples, dark and erect. My breasts are somewhat larger, and while they are no where near female proportions, they definitely showed. He seemed to enjoy this and without further adieu he leaned in and started sucking on the right breast. I tilted my head back and began moaning softly and without control, "Oh my, oooh, Ohh, ohh..." I could not stop myself from moaning. I looked down and saw his massive bald head bobbing up and down. He still had some hair on the sides of his head, his ears were large and there was silver/gray hair coming out from seeming every corner but the top of his big head. I kissed his head. With a flick of his left arm he pulled my entire body over to move my left side closer to his waiting mouth. He took my left breast in his mouth. Meanwhile, his right hand started moving up my exposed right thigh. He began to move his hand slowly up my shorts and he stopped just short of my mound. By this time, I was rock hard and my shorts were loose and so I was completely exposed exposed. By instinct I had opened my legs for him, waiting for his big, thick hands to explore all that I had to offer him.

He looked down and saw my 7" erection. He stopped sucking on my breasts and stood up and grabbed me by my hand and led me to his bed. He threw me down like a rag doll and opened my legs. He groped me wildly with his hand up my shorts. He had large beefy fingers which completely engulfed my cock. I looked so small under him. Effortlessly, he pulled off my shorts, exposing me completely. He also yanked off my tank top, making me completely naked. My nipples were erect and I was begging myself not to cum. I had never felt this way before and I stopped just short of begging him to fuck me.

I realized that Roger was not much of a talker. He was friendly enough, but he pretty much stuck to minding my body. He seemed genuinely attracted to me and was having difficulty controlling himself in spite of his experience.

He hastily pulled off his shirt, revealing his massive upper body. It was covered in a thick mound of silver/gray hair. His belly was hanging over his shorts. It was massive. He pulled off his shorts, and much to my shock and horror, he had a short but extremely thick cock. It must have been around 5" in length but it was definitely thicker than mine. His belly seemed to belie the full length of his cock and this also scared me but I was still determined to please him in every way I could.

I lay there naked in this strange man's bed, wondering in amazement at how, within minutes of meeting this man, I was naked and completely open to him for the taking. He climbed into bed. His imposing figure towered over my much smaller body. My legs were slightly open in anticipation but he pushed them apart fully and got on top of me. I felt crushed under his weight. He first came up close to my face and kissed me and licked my ears and nibbled on my ear lobes. I could feel his hot breath in my ears as he whispered "You're very sexy, I'm going to have fun with you tonight," to which I mustered a response, "I'm yours, baby." He couldn't hear me. He pinned my hands down by my head and he kissed me. His large tongue was deep in my mouth again. I kept biting his lower lip. He was a really good kisser...

"You must have done this a lot huh?" I teased him. He ignored me, and grunted. He then placed his attention on my breasts and started sucking on them again. I am extremely sensitive in that area and this was bringing me to an orgasm.

I was squirming under his body and I was struggling to wrap my legs around his much larger body. He had so much power over me. I finally started grabbing the sheets as he nibbled and licked my nipples and I was moaning uncontrollably. I didn't want him to stop, but at last he did...moseying his way down between my sternum and then to my flat stomach. He kissed me all the way down. I didn't realize it at first, but I started saying his name, "Oh Roger, oh baby..."

He grabbed my thighs and spread my legs wide and buried his face between my thighs, taking me all in one gulp. I gasped and couldn't stop saying "Oh fuck, Oh yes!" repeatedly as he sucked me.

He remarked, "Oh, you shaved?!"I did leave a thin "landing strip" for him, but he clearly liked it as he moaned and groaned with my cock in his mouth. His thick fingers made their way up to my breasts and he started pinching and touching my nipples ever so lightly. This drove me crazy. I kept squirming and looking down at him, my eyes pleading with him, part of me begging him to stop but the rest of me begging him to continue forever. No man had ever made me feel this way...I wanted to cum so badly but I kept grabbing the sheets with my hands and opening my legs wider and wider to accommodate his large head which looked humongous between my thighs. Every so often, he would pause and moan with his deep voice while my cock was still in his mouth. His voice reverberated throughout my much smaller body. He grabbed me by the ass and lifted me straight up and started eating my asshole.

I felt pangs of pleasure deep in my stomach...I kept grabbing his head and massaging it. He would drop me down and my erection would be right there near his mouth and so naturally he would swallow it again. Several times I found myself on the verge of a huge orgasm so I would push back lightly on his head and plead with him "Please no, please baby not yet you're gonna make me cum..."

He smiled and put his finger up my asshole in response. He swallowed my balls whole. Every part of my body seemed relatively tiny compared to him. I realized many times during the night that he completely dominated me and made me feel so small and slight. I submitted to him completely.

He flipped me over unto all fours and dragged me to the edge of the bed. He slid off the bed and went down on his knees. My ass was in the air, my knees were spread apart, he began eating me voraciously. I buried my head in the pillow to drown out my moans and screams. He would reach up and grab my cock and alternate between eating my ass and sucking my cock. He rubbed his hand against my belly and caught my breasts a few times. I turned back and could only see his bald head buried in my ass. My legs were spread open as far as I could spread them for him.

Suddenly, he stood up and grabbed me my hand and told me to get on my knees.

I knew what was coming. His thick cock was wet with precum...dripping on the floor. Gray hair surrounded it, making it a sizable mound. His balls were remarkably huge as well. I noted the strong odor of sex down there...I looked at it for a second, studied it, then started licking the tip of his cock...

He began groaning and moaning, grabbing my head with both hands. He put one leg up on the bed and then he used more force to push his cock all the way into my mouth. I almost gagged...I wasn't accustomed to this sort of aggressiveness and I certainly had not expected it from him but I found it strangely arousing. His cock was certainly longer than it first appeared and my mouth was completely full. I looked up at him but could barely see his face as his massive belly was in my view. I kept hitting his belly with every suck and a mixture of my saliva mixed with his pre-cum began dripping down my chin and unto my breasts and my thighs as I was kneeling before him. I tightened my suction and he groaned more and I thought I heard him say, "That's it, beautiful," or so I imagined. He reached down and played with my nipples.

I took a second to stop sucking his cock and then I went under and started licking his balls while masturbating his cock with my left hand. His moans grew louder...he obviously approved and then he pulled me up. We kissed again and he reached down and grabbed my cock while we kissed, taking my breath away...then he lay down on the bed and he pulled me next to him. I lay there in his arms for a while, staring up at the ceiling. It was dark in the apartment, aside from some dim lamps. I took in the night and while I still had some inhibitions in me, I forced them out, choosing to live in the moment. I turned to him and kissed him. My legs were spread open and he groped me while we kissed. I enjoyed watching him grope me. His hands were massive, just as the rest of him and my cock looked tiny in his hands. My legs were smooth and long, in stark contrast to his thick and hairy thighs. He put his leg over mine to keep them open. He reached over and started sucking on my right breast again. I moaned and closed my eyes and turned away and I could sense him looking at me, watching me as I reacted to his moves.

I sat up and kneeled next to him and began stroking his cock. He had become flaccid during our small break so I took his cock in my mouth. My ass was in the air again and I was leaning over him as he lay on his back. He reached over with his left hand between my legs as I was bent over on all fours and he started playing with me, jerking me, then reaching up and fingering me.

I moaned with my mouth full of his cock. He then grabbed me by my waist and hoisted me over his face. He sucked and ate me out while I was straddling him. My ass was in his face. He reached up with his hands and started touching my breasts. I looked up at the ceiling and moaned. He then pushed my head down to his cock. We were in a 69 position and I loved it...I lost track of what he was doing down there as I was so fixated on his thick dick which had no shortage of pre-cum. His cock had long since regained its full girth and size. I kept pulling out and spitting on its head then licking the tip of his cock. I sucked harder on the tip and I felt his approval as he sucked on me.

Finally, he pulled me back to lay down next to him in his arms and he smiled. I had made up my mind even before we met tonight that I wanted him inside of me. So I asked..."Do you want to fuck me?"

I never thought I would ask...it was kind of amazing that I had been with several men during my college years, some of whom I was quite attracted to, but I never gave up my virginity.

At least not until tonight.

To be continued...