Losing My Virginity

A Chubby Chaser's Autobiographical Tale

Episode 1: First Contact

Hi, my name's David. I've known that I was a Chubby Chaser my whole life. I'm apparently "hard wired" for it. But, knowing what you want doesn't necessarily help you get it. This is the tale of how I finally "got it".

Right after graduating High School, where I had been completely closeted, and just prior to this story, I had awkwardly tried to form relationships with a couple of chubby guys from my graduating class without any success while losing two good friends in the process. At least I didn't get beat up for trying.

I wondered if anything could ever work out. I had no experiences and no resources of information beyond anatomical diagrams and unhelpful definitions from the Dictionary and Encyclopedia.

At the beginning of this tale, I was an 18 ¾ -years-old, fairly tall but scrawny, naïve and immature kid with no muscular development, the proverbial "99 lb. weakling" with zero body hair and very little pit or groin hair. In my favor, I was decently hung (although only I knew it) and had a face that was considered "adorable" and had "nice hair" according to a few girls in school who I avoided as politely as I could, per the strict manners I'd been taught. I wore my dark brown hair long, past my shoulders. It was full and styled with natural barrel curls, reminiscent of Barry Gibb's hair in that era, but longer.

I was a soft-hearted, shy and introverted book worm type who was desperate for something to click with someone, somehow. Now on to the story.

In the late summer of 1981, I was yet again cruising the convention hotel near our house in Lubbock, TX. This time they were hosting a Precious Gems and Precious Metals conference. Following my regular circuit, I emerged around a corner to see a gorgeous, well-rounded, grandfatherly man. He wore a white suit shirt, tie, nice-looking navy-blue dress pants and matching shiny patent leather dress shoes as he backed out of one of the hotel rooms, still talking to an unseen person inside. I froze in place. This was the first sexual candidate I had ever found at the hotel.

He was around 6' and 320 lbs. compared to my 5'10" and 120 lbs. His hair was silver tinged white and full but business man short. His beard was snow white, a goatee with an inch-wide run along the jawline. Both his hair and beard were well groomed. His lips were full and inviting. His nose and cheeks reminded me of the classic Coca-Cola Santa Clause. His eyes were metallic blue and dreamy. His thighs were stoat and rounded. His hips were wide and his ass was rounded like he was hiding two basketballs. His belly looked like a small beach ball. "Absolutely perfect!" I thought to myself. His apparent age of perhaps 50 something was an unexpected but powerful turn-on. His confident, masculine bearing and powerful Bass voice had me weak in the knees moments after first seeing him.

He glanced my way, sizing me up as I had tentatively begun gently rubbing my crotch and licking my lips, visibly trembling, standing 10 feet away from him. He rubbed his thigh in response. My heart jumped and I stopped breathing. My head started to spin.

He finished talking to the person in the room and then headed my way. As he passed me, he whispered in his deep voice, "Lobby, 1 hour." Stunned, I wondered if I would have a seizure while I thought in disbelief, "This just happened, right?"

I waited for nearly 2 hours as the sun set and was beginning to worry he wouldn't show. I probably would have waited all night, but he finally breezed through the lobby looking extra dapper now in his full, well-fitting navy-blue suit and a grey fedora with a baby-blue band that suited him perfectly as he headed to the Men's Room nearby. I waited long enough that it would not appear that we were meeting there and entered the same Men's Room.

We were alone. I was trembling again in the presence of this "Man's Man." I was anxious about my lack of experience and hoped I could please him and satisfy his needs. He growled his order, "On your knees, Boy!" I immediately complied, relieved and thrilled that he would direct the action, leaving no doubt what he wanted.

He unzipped and produced his already erect, rather thick 6.5" circumcised member that tapered at the pink head. Just as I was ready to start, someone hit the outer door on their way in. I jumped up to the sink and he jumped in front of a urinal, putting himself away and then flushed, following me to the sink as I left. When he re-emerged, I nodded for him to follow me to a more secluded restroom near the unoccupied indoor pool. Once inside, we resumed our tryst as he unzipped and pulled out his stiff member, already glistening at the tip.

As I took him in hand, I felt an initial wave of passion that wiped away all my trepidation. I guess instinct or maybe past life experience took over as I unconsciously guarded my teeth with my lips and twirled my tongue lovingly around the tapered head, tasting the salty sweetness of his natural lubricant. The taste of him had me swooning and my mouth watering as I took that head directly into my throat without gagging and gripped it tightly with my throat muscles. With my face planted firmly in his soft groin, I had managed to get him past my Adam's Apple. His, "That's it, Boy. Squeeze it tight!" had me grabbing at it with my throat until I finally had to back off slightly for air.

As I worked my way back up, I lavished my tongue around his shaft like it was a frozen popsicle treat, wagging my head. I flicked the front tip just below the slit 5 or 6 times in a quick, fluttering motion at the top of each stroke before diving back down to start the cycle again, all the while rapturously caressing his belly and thighs and firmly squeezing his ass automatically, totally lost in the moment.

Each deep-throat clench and tip flick blitz (try saying that 3 times fast) elicited a growling grunt or huff accompanying a quick, involuntary spasm from him that seemed to travel through my body in a wave, driving my passion higher and higher. I slowly increased my pace while maintaining my somehow innate oral acrobatics.

When I checked, the awed expression on his face and in his eyes confirmed that my efforts were being well received. I swooned again at the affirmation and returned to worshipping his whole being with my mouth and hands, whimpering my deeply emotional response. This was the most perfect moment of my life to this point. I felt that we were one, that he completed me.

After about 3 minutes of this treatment, his breath quickened as he grabbed handfuls of my long hair on either side of my head, growling, "Here we go!" I let him take over without hesitation. He pumped 3 quick thrusts before slamming home, emitting a series of hushed, guttural grunts and snorts as he shot repeatedly into my throat sending volumes of his hot load both down my throat and up into my sinuses in 6 sizeable bursts.

Thrilled to be fully under his command and riding the wave of his response, I had a full body orgasm matching his climax, moaning and quivering as I gulped and happily swallowed my creamy reward then ran my thumb up the front of his shaft to get every last drop. I kept him in my mouth even after he released my hair, suckling and savoring our connection, wanting this moment to never end. I felt him trembling as he gently stroked my hair.

When he caught his breath, he withdrew from my mouth and used a white monogrammed handkerchief that read ' B T ' to clean himself off before tucking his deflating member away and zipping up while my body continued to tingle all over. I noticed my precum wet spot had seeped through my briefs, pocket material and jeans and was the size of a silver dollar.

He looked astonished at this young man's enthusiastic, passion-filled debut performance when he helped me up from where I had slumped from my kneeling position and asked, "Where'd you learn to do that?" I replied with a thankful, intoxicated smile, "It was my first try. I guess it just came naturally."

I realized immediately that I had just admitted to being a virgin. He looked around, seeming conflicted about his next move. He finally pulled out one of his business cards and handed it to me as he slipped away without a further word.

From the card, I learned his name - Brian T, the name of his business, his title along with an office address and phone number. He was the owner and president of a Diamond and Gold exchange company. He was obviously in town from Dallas for this convention of buyers and sellers. The last 4 digits of his office number matched the last 4 digits of my home number. That's a 1 in 10,000 chance. I had hit the lottery in more ways than one, I thought with a grin.

I stashed the card in my wallet and went straight home to relive the experience alone in my room while I was still able to smell and taste his essence. After 3 heart-pounding releases, I hugged my oversized pillow, closed my eyes and drifted happily into the land of Nod where I had a wonderful dream about laying with him in his bed, safe and secure, wrapped in his arms.

Episode 2: Trip to Paradise

Six months later, after having been kicked out of my house by my asshole/homophobic father, I was feeling very lonely and horny in my tiny but affordable converted garage studio apartment with only a small AM/FM clock radio and my guitar for company.

Thinking back to when he had given it to me, I pulled Brian's card from the secret fold in my wallet and decided to write him a letter. I wrote that I had really enjoyed his company during our brief time together the previous summer and that I'd love to see him again if ever he returned. I dropped my missive in the outgoing mail and went back inside to pleasure myself to yet another mental recitation of our previous episode.

To my surprise, he wrote back with a date and time I should expect him to pick me up with instructions to dress my best. I showered, scrubbing myself thoroughly, brushed my teeth and shaved my peach fuzz, using deodorant and a touch of English Leather aftershave and cologne in preparation. I blew my hair dry and was pleased with how it looked, very bouncy and carefree. I was equally nervous and excited as I awaited the appointed time.

He arrived as promised and took me to his nearby, high-end Hotel. His rental was a full-sized Lincoln Towncar. He wore an expensive looking and apparently tailored black pin-striped suit with a daisy in the lapel that popped with his white hair and beard and set off his blue eyes. Next to him on the seat was a white banded black fedora. On his right index finger, he sported a big, masculine, gold ring with a large embedded Yellow Topaz, a 1" by 1" square cut gem. Boy did he look good.

I told him I felt way under-dressed, but that these were the best clothes I owned, a tan dress shirt, brown bell-bottomed Corduroy pants and a well-worn pair of dress shoes. He said I looked fine and not to worry. I slid across the seat to reach and caress his thigh, grinning broadly, while he smiled and ran his fingers lightly through my hair during the short drive.

He draped his arm across my shoulder, presenting the jeweled ring for viewing as we approached the hotel bar. I was old enough to enter any bar in Texas at that time, but hadn't tried drinking yet. He proudly lied to our greeter that I was his Nephew and it was my Birthday, perhaps to justify our closeness. We had never discussed my age and I wondered if he thought he was sneaking me in. I did look younger than my actual age. He tussled my long hair over my eyes and grinned at me convincingly with pride as I grinned back, sheepishly blushing and rearranging my hair.

We were seated at a secluded, candlelit booth in the sparsely populated bar. An elevator version of Lionel Richie's 'Endless Love" murmured in the background. I giggled inside at the ironically appropriate timing. I smiled, sighed happily and looked deeply into his glorious eyes only breaking my gaze as our server arrived.

Brian ordered a double snifter of their longest aged Glenlivet Scotch, neat, and a frozen Strawberry Daiquiri for me made with a top shelf dark Jamaican Rum and fresh strawberries with rich cream. My drink arrived in a Hurricane glass complete with a tiny umbrella shading a fresh strawberry on top.

As I took my first tasty sip through the fat straw, I watched intently as he swirled the fine Scotch around the snifter a few times, palming the underside of the glass. He closed his eyes before taking a full breath slowly in through his nose over the lip of the glass with an unconscious smile emerging on his face. Holding that breath, he then took a small sip, lightly swishing it around his palette and swallowed before finally exhaling through his nose. He sighed in a sensual bearish growl as he exhaled and that smiled returned to his face.

When he finally opened his eyes, his smile quickly turned into a grin as he noticed my expression. I was enthralled. Never before had I seen anyone drink so passionately. He continued grinning and said mischievously, half under his breath, "It's never better than the first time." I blushed and he chuckled in a Baritone range. He had a precocious gleam in those dreamy blue eyes.

I had found my drink to be delicious and we both finished the first round about the same time as Brian signaled our server, wagging his ringed finger in a circle. After three rounds and lots of friendly, inconsequential banter and jokes, he signed the bill to charge it to his room and left a $20.00 tip on the table.

We then boarded the elevator to his Executive Suite on the top floor. As the elevator doors closed, he took my skinny hand in his plump paw, dwarfing it. I was happy as a clam and feeling no pain with a foolish grin on my face. As he led me to his room, I had to resist the urge to skip down the hallway.

Once inside the spacious Suite, he pulled me into an urgently deep kiss, my first, while enveloping me in his strong arms. I could taste the lingering, smoky Scotch as my eyes rolled back in my head and my eyelids fluttered in a passionate delirium, our tongues wrestling. After a minute or so, he stepped back and ordered me in an intense growl to, "Strip, Boy!" as he did the same. His dominating tone sent a semi-orgasmic shiver down my spine. I knew I would willingly submit to any command. He was in total control and it felt totally right and natural to me.

He carefully placed the elegant suit parts on a chromed suit stand by the wall as I folded my clothes and placed them on a wing-backed, ornately upholstered chair, noticing the excellent view of the downtown lights.

I marveled, wide eyed at his naked body as he finished undressing. For all of his weight, nothing sagged. His chest was covered in soft white fur. His breasts were full and firm. His skin was surprisingly pristine and unscarred. I went to my knees in front of him and reached for his egg sized testes beneath his erecting member that jutted out from a snow-white bush at 60 degrees and bouncing higher with each heartbeat. Brian had other ideas as he lifted me up silently and effortlessly to lay me tenderly on the bed.

He placed me on my back on a bath towel that had already been laid out for me with one pillow placed perfectly for my head and another to the side of the towel, down at my hips. He placed my heels just below his shoulders with my knees bent to accommodate his ample belly as he stood at the foot of the King-sized bed. I totally knew what his intentions were and I was more than ready for the experience. I shuddered inside with anticipation knowing this was a moment I had been waiting for since puberty.

He raised me gently and slid the 2nd pillow under my lower back, effecting a more comfortable angle of attack. He grabbed the small bottle of lube that had been strategically placed under the 2nd pillow and hurriedly smeared my ass crack and slicked his now very stiff missile. He quickly lined things up then penetrated me and sank balls deep into my virginal depths in one swift move, holding there. My system spasmed and clenched wildly at the sudden invasion. I felt a shiver from his loins and I heard him exclaim in his gravelly Dallas drawl, "Damn, Boy! That's Better 'n Biscuits!"

Meanwhile, my eyes couldn't have opened any wider as I stifled my scream, biting my wrist so hard I broke the skin. He paused for a few more seconds, still hilted, while I started to adjust. My scream quickly reduced to a whimper. He then applied 5 or 6 deep, sensual warm-up thrusts as any remaining pain subsided, replaced by a euphoria as I felt him steadily tagging what I later learned was my prostate with each pass. As he watched my face to see when I was ready for more, I plummeted into those blue eyes.

When he started up a slightly quicker pace, my body began to tingle from head to toe and my rock-solid 7", standard width, cut manhood began to ooze copiously from the repeating stimulation of my prostate. Precum pooled in my navel and painted my lower stomach as each stroke seemed to push more of it out.

He noticed the sheen on my abdomen and got a gleam in his eye as he gathered my feet together so he could suck on my toes while starring at my reaction, still pumping me steadily. I thought I'd loss it right there, but he'd pause before edging me again. I felt my brain crackling from the massive, overpowering input.

As I neared sensory overload, I felt reality shift. We were connected at a cellular level. Time dilated and we were on a planet of our own. Nothing outside that bed mattered or even existed.

He apparently stopped the foot service when he noted my glazed, altered state. As I descended back to earth, I noticed his eyes were a little glassy and puffy as he grasped my forearms and I started moving into his quickening thrusts while I consciously synced my breathing with his. I continued to watch his facial expressions and tapped in to his experience, feeling his lust and pleasure as my own. He seemed to be feeding off my passion as well in a self-perpetuating cycle.

He was breathing heavily when he eventually slowed to his initial warm-up pace, dropping my arms and grabbing my thighs while grinding his strokes and rotating his hips, giving us both a new sensation. After catching his breath, he suddenly paused to glide his hands over my concave stomach and barely perceptible pecs. He had a soft expression on his face when he said tenderly, "So soft...So smooth."

He had dropped a barrier but threw it right back up. He looked me in the eye with a crazed expression and asked rhetorically in his commanding growl, "Are you ready, Boy?!?" I whimpered a pleading, "Yes, Sir." with tears of joy and desire welling in my eyes.

Closing his eyes tightly causing his nostrils to flare, he hugged my ankles tightly against his soft, furry chest and began pounding me with quick, full-length, punching strokes. I fisted the bedspread on either side of the towel, arching my back and kept my raptured gaze on his face. His animal passion was mine. As his body tensed and his breath caught, so did mine. Once he slammed into me one last time and gasped his ultimate breath, we exploded simultaneously in mutual ecstasy. I plastered my left cheek with my first volley and I could feel him pulsing deep inside me as I clenched the base of his shaft tightly with each of my successive bolts.

He collapsed forward over me, still hugging my ankles, folding me in half and placing his forehead on mine as we muffled our grunts and curses. We panted hard for a minute before catching our breaths and separating. "Wow!" I thought. I just experienced my first hands-free climax and the best sex I could have ever dreamt possible. In the afterglow, my body continued to tingle and I felt like I was floating.

Conclusion: The Reckoning

After quick, separate showers, we dressed to leave. He hadn't said a word or looked me in the eye since our climax and I was too apprehensive to break the silence. I was filled with worry as he dropped me off back at my place, finally speaking to tell me goodbye and to thank me for a great evening with a quiver in his voice and a pained grin, his eyes slightly moist. It was far from the happy grin that I hoped it might be. That look really pulled on my heart strings.