I Prostituted Myself to a Bear

My name is Ishan. I'm 20 now but during my freshman year in college, I had sex with an old man in exchange for money. This is the story of that night.

Growing up in a conservative and traditional family, I always struggled with the idea that I was attracted to men, particularly the old grandpa types. I hid it as a child and pretended to enjoy spending time with girls in our circle of family friends. When I got into college, that all changed. My university was 4 hours away from my parents' house and it afforded me an unexpected freedom.

Unfortunately, we didn't have much money and so while I watched as most of the other kids moving into the dorms for the start of fall semester were driving in with their lifted trucks and SUVs, my parents dropped me off in our 15 year old family minivan. I also didn't receive much of a sendoff from my parents either. They simply dropped me off and left me at the entrance to my housing campus. It was a state school and I was on scholarship for tuition plus a secondary scholarship that I was able to use for books and we were able to qualify for some financial aid, but money was tight otherwise.

I had a tough time my first month in school. Although I was considered pretty attractive and found myself getting quite a bit of attention from the ladies, my financial situation weighed on me and affected my self-esteem. I found a job on campus at the bookstore, but I could only put in so many hours while balancing a full course load.

One lonely Friday night I was browsing through listings on Craigslist and made my way over to the "Gigs" section. Under "Talent" I saw what appeared to be an ad for "Looking for Male Model". Out of curiosity, I clicked on the ad.

"Looking for a male model, prefer in town, prefer college age but no more than 24 years old, athletic build. Earn up to $3000 per modeling session. Send pics and some details (age, location). Can be an ongoing employment opportunity!"

$3000!! I was shocked. Interestingly, the ad was fairly light on details, but I did see "m4m" headlining the top and bottom of the ad.

I looked through my computer and found some pics from a trip we had taken to the beach over the summer. There were some decent single shots in there. I began shivering with nervousness and some trepidation as I clicked the link on the ad to send a response.

Within minutes, I received a reply. I was surprised and my heart began racing as I saw the subject line.

"Re: m4m Model"

Hello Ishan

Saw your e-mail and pics. You are very attractive and we would love to meet you to talk more. You have a car?

Frank"

A phone number was included next to his name. I took a deep breath and slowly dialed the number. A deep gruff voice answered. "Hello, this Frank speaking."

I let out a gasp of air and my voice cracked as I stammered, "H-hello?? I was calling about the e-mail?" I was so embarrassed.

"Uh-huh...yeah..you got a car or something?"

"N-no sir..I'm sorry.." I stammered as I continued to struggle to find my voice as my throat felt so dry.

"That's fine. You in school? What are you, a freshman or something?" Frank asked, his gruff tone making me even more anxious and nervous.

"Yes sir. I just turned 18 a month ago.."

"Mmm...yeah, I know, young but legal.." he snorted a laugh. "K. Yeah you are definitely not what I was expecting, you look like a model. Why don't I stop by and get you and we come back to my place and we can hammer out the details? I'll be there in an hour."

"Ok..ok yeah that's fine." I gave him my address and he hung up.

I didn't know what I had just done and the shock of this suddenly weighed on me but I also couldn't stop thinking about the money that was being offered. It was starting to get dark outside, but thankfully the weather was still in the 80s and I was able to slip on some 2" running shorts with high splits I used for cross country in high school. I also pulled on a low cut tank. It was awkward wearing these as they had my high school name emblazoned all over them. I slipped on my flip flops and went down to the main campus gate. By that time it was completely dark, and I was thankful for this since I didn't want to be overly conspicuous.

Now, a bit about myself. I was definitely a little guy. I ran cross country and was pretty athletic my whole life, but I also did martial arts, soccer, cultural Indian dancing, and swimming. On my best day, I was 5'4" and weighed 135 lbs soaking wet. Puberty seemed to have barely affected me, as I was naturally hairless and smooth all over and I had never required shaving anywhere. I suppose in this particular situation, this was ideal.

Not long after I made my way to the street corner, I saw a small older model pick-up truck pull up ever so slowly next to me. The windows were rolled down already.

"You who I'm lookin' for?" It was Frank.

"Mm-hmm." My heart must have been going 200 beats per minute. Frank was easily in his late 60s, had a trimmed gray-white beard. He looked to be overweight, but not obese or anything. I opened the door and hopped in. I saw Frank look me over and he grunted what I interpreted as a sign of approval. My shorts were riding high and with the splits, they were up to my hips. I had lathered myself with some body lotion so my legs were glistening with the lights.

"Nice to meet you. You look even better in person," he chuckled. "So the plan is to go back to my place. The money will be paid out with some up front and the rest after. You look like you are ready to get some pecker inside of you. You like gettin' fucked my old men?!"

I was taken aback by his bold questioning as it did also bring to light why I was subconsciously dressing how I was tonight. I was an inexperienced virgin, yes, but I also wasn't so naive as to think $3000 was being given just to "model". I was startled regardless and I looked down before responding softly with a nervous laugh, "Yes...I've never been though...is that ok?" I looked up at him, searching his face for an answer as his eyes were fixed on the road ahead.

"Yeah, should be fine, first time is always the roughest, but gets easier! At least that's what I think, I never had a pecker up my ass though! HAHA!"

I clasped my hands together as we drove in silence. He was clearly a big man, sitting in the seat next to him in this single cab pickup truck, the top of my head barely reached his shoulder. His thick hands were hairy, his belly bulging, the buttons on his shirt were fighting to keep from popping. He was wearing jeans and boots. I was wondering how long it would be before he was inside of me.

We finally pulled up to a trailer park just outside of town. The park had only one other trailer and looked as if it had largely been abandoned. Signs of decay had set in on the lot as there was overgrowth of weeds and bald spots in areas previously occupied by trailers. I did at this time fear for my life, albeit this was just for a moment. I hadn't realized it during the ride, but my brief liner was wet from precum. I hopped out of his truck on to the sandy dirt driveway and watched as the small pickup shook violently as Frank exited. I gazed at him lustfully at his 6'1 stocky frame. He lumbered up the few short steps and opened up his door and stood aside as he waited for me enter first. The lights were on and I was greeted by the stench of cigarettes and urine and dirty laundry. There was a kitchen off to the right of the door and to the left was an L-shaped sofa up against a wall. A small TV was against the opposite wall and a twin bed and small bathroom next to that. Cigarette butts, open beer bottles, old magazines littered the trailer. The sofa was red at one point, it looked old and had one section with a chaise attached. The vinyl walls looked like they were imported directly from the '70s with their light brown faux wood appearance. The fear for my life returned briefly, but then - "Make yourself at home! How do you pronounce your name? I-Ishan? Where is that from? Sounds like a girl's name, heh!" Frank said as he closed the door.

"You said it right, it's Indian, that's where my parents are from," I responded back.

He cracked open a beer, "You want one?"

"No thanks," I declined politely.

"You ever been with an Indian man before?" Frank asked.

"Mm-mm, nope," I let out a soft laugh.

"Ahh...you like interracial crap...you been with black or Mexican or Asian? Oh, that's right, you told me you're a virgin. But you never sucked dick or fool around?"

"Mmmm...no, I mean I guess if I had to pick, I wouldn't say no to a Black guy..." I said softly. I brushed off some cigarette ash from a place on the red sofa and sat down and crossed my legs.

"I bet you would, sweetheart, but I'm glad you didn't say no to White tonight. FYI, my cock don't work too good, you can stroke it and suck on it a little if you'd like, but it's my buddy Gary you're going to be with tonight...sorry, I meant to tell you that before."

My heart sank, but I barely had time to process when I heard some footsteps coming up the wooden steps outside and loud knock on the door.

"It's open!" Frank said. The door swung open and in barged in another large old man. This was probably Gary, I surmised. He looked a few inches taller than Frank and had a gut. He was wearing worn khaki shorts and a T-shirt over some construction boots.

"Gary, meet...uh, Ishan, Ishan, Gary.." Frank said. Gary looked like he was huffing and puffing a bit as he strode over to wear I was sitting and I raised my hand to shake his and he took it gingerly and kissed the back of it, much to my surprise. He let out a deep groan of approval as he licked his lips and then plodded down right next to me on the sofa.

I was super nervous as he put his left arm behind me on the sofa back against the wall. "Nice to meet you, is it...how do you say your name, doll?"

I was again struck by his demeanor. "It's Ishan, like eye-shaan," I replied, my voice shaking in fear.

The top of his head was bald, he had some wisps of white hair off to the sides and back, he had a trim goatee and mustache outlining thick full lips. He wore thick rimmed bifocals that gave him a bug-eyed look. Thick mounds of white hair were popping through the collar of his T-shirt and his arms and legs were similarly covered in hair. He had tattoos on his right arm, each of his fingers looked thicker than 2 of mine. All in all, he was a very large man, but also very creepy looking.

And yet I found myself quite attracted to him as I tried hard not to stare at him, my hands were clasped and my legs crossed. He never once took his eyes off me. Frank came and sat down on the twin bed and propped up his leg and leaned back against the wall.

"$3000 if you have sex with Gary," Frank started. "Here, I'll give you $300 up front. First, let's see that ID of yours, make sure you're not lying to us."

The shock of being propositioned for sex was still something I was reeling from, but I took out my ID from the secure pocket and Gary took it out of my hand.

"Under 18 it says here...oh wait, there's the birthday. HAHA, you just turned 18 like a month or 2 ago. You must be desperate for money or cock or both to be willing to fuck a 70 year old gramps!" Gary said as they both laughed out loud, much to my embarrassment.

He tossed my ID to the side and began to lean in closer to me. "Where you from? You have that exotic look about you?"

"My parents are from India."

"Ahhh...land of Kama Sutra...exotic indeed. You look even younger than 18, but the ID says what it says, and you look stunning. Look at those strong muscular legs!" His hand grazed my thigh.

"You agree with the plan?" Frank asked, as he sat back with his knees open, beer in his hand dangling between them.

"Mm-hmmm..." I said softly, and looked down.

"Oh, there's no need to be shy, sweetheart, I'm going to be deep inside of your sweet boy pussy in no time!" Gary whispered into my right ear, his voice deep and breathy. I bit my lower lip as I looked up at him and he leaned in and cupped my jaw with his big right hand and put his mouth on mine, shoving his tongue deep into my mouth.

I gasped and gripped the sofa cushion with my hands as he pinned my head against the sofa back, his tongue was so thick and rough and felt so long inside my mouth. My eyes were closed as I began reciprocating him, my body slowly relaxing. He seemed as desperate to take me as I was to give myself to him. His breathing became more intense as he let out intermittent grunts almost complementary to my soft moans and gasps for air. His saliva trickled down from the sides of my mouth and not before long, I felt his hand ease off of my jaw and slowly slide down towards my chest. It lingered for a brief moment, then started lightly grazing my left nipple through my tank top.

I moaned again and clenched my eyes shut as his grazing motion intensified, making circular motions with his finger pad over my left nipple.

"Oh Gary, I think he likes that!" Frank said. I had reflexively uncrossed my legs and started to spread them a bit, the more Gary played with my breasts.

"Oh yeah, you do like that!" Gary took a break from making out with me, as I was breathless and his saliva was all over my lower face. I nodded quickly as he pulled up my shirt, then must have gotten frustrated and just ripped it open from the center. My dark nipples were erect, my olive brown smooth skin was still glistening from the lotion. I looked up at him, silently begging him to put his mouth on them. He leaned over and began flicking his tongue lightly over my right breast, cupping it with his massive hand.

"Oh, God, oh God, oh God...." I clenched my eyes shut and thrust my head back towards the popcorn ceiling and my hands gripped the sofa cushion.

"There ain't no God here, baby doll," Frank teased. "Just your tiny virgin ass in this dank old ass trailer getting fucked by gramps!"

I kept breathing heavily and moaning and biting my lower lip. I touched his face with my left hand my body squirming and shaking as he would flick his tongue followed by full on sucking on each breast, all while grazing and pinching my other breast.

"Oh...Mister Gary....ohhhhh...never felt this before...ssssss!!" I squealed. He put my right leg over his left knee and began running his hand up my thigh and into my shorts but was met with the brief liner. He pulled it to the side and began groping me and stroking me with the palm of his rough hands. I almost came then but had to distract myself.

"Let's go ahead and get these little shorts off and that shirt, you won't be needing them tonight!" Gary laughed.

My tank was ripped so I just pulled it off, then leaned back and folded my knees up and peeled off my shorts. "Prop your feet up and spread your legs open for this old man!" Gary requested. I did as I was told. Gary took my shorts and sniffed the brief liner and then licked the inside.

"Mmmmm...sweet tasting, just like 18 yo pussy!" Both he and Frank laughed out loud at that. "Amazing body you have there, look at that little brown cock and balls."

I didn't consider myself that little, did hurt my feelings a bit. I was 7.5" and had decent sized balls, or so I thought.

"My turn!" Gary yelled out. He pulled off his tee, revealing his massive and hairy body. He had on a gold chain and big gut. He leaned in close to me and we began making out again. He stopped before shoving his finger into my mouth and I instinctively began sucking it while looking up at his face, my cheeks sucked in. He pulled out and put his finger in my ass crack and then started to rub it on my balls then slowly over the shaft of my dick. Then he slowly grabbed my dick with his hand and began stroking me as I began moaning softly once again.

"You like being jerked off by a dirty old man, don't you?" he asked as I gasped out a yes. I kept biting my bottom lip as he stroked before spitting into the palm of his and spreading it on his finger. He grabbed my right knee from the front and spread my legs open and found my asshole and slowly inserted his thick wet finger. I gasped and grabbed his thigh with my hand as I didn't expect his finger to feel so thick inside of me.

He began pumping his finger in and out of me rhythmically, as I squirmed deeper into the sofa cushion. My eyes were closed so before I realized it, I let out a shriek as I felt him start sucking on my breasts. My back arched as I almost came. I was breathless. At that moment I thought to myself that I must have done something good in my life to be feeling the things I was feeling.

Gary stopped sucking on my breasts and came up to my face and kissed my cheeks and then we made out once again, but this time I started holding his face more affectionately as I was really very much into him. He had stopped fucking me with his finger and had since gone back to groping me and stroking me and my inner thighs were wet with precum.

He slid over to the part of the sofa with the chaise. "Have a taste of gramp dick, my little brown princess!"

I crawled over to where he had reclined back with his legs sprawled out and straddled his big left leg. I was on my knees with my ass up in the air and I slowly undid his belt and he helped me pull off his shorts. As I had guessed, he was tighty whities. His briefs had a large brownish yellow stain right at the center of the crotch area and as I leaned in to pull them off, I caught the stench of an old man. I ignored it and struggled to pull off his briefs, but managed to get them off with his help.

It was quite a sight to behold, staring at this man's penis. He was uncircumcised and it was easily twice as thick as mine and at least 2" longer by a conservative estimate. He saw the fear in my eyes and the two men started laughing uproariously.

"You look like you've seen a ghost! What - you didn't think a pecker could get that big? We're in 'Merica, princess! You better get to work sucking on that thing instead of just looking scared! You wanna get paid, you gotta get fucked! You can't back out now!" Frank yelled, now in a more drunken state than he was before.

I was terrified but also horny for it and curious. My nipples were still sore from him sucking on them, but Gary didn't seem to care as he leaned forward and pinched them again before grabbing me by the throat and kissing me deeply.

"You can take this cock, I felt that little pussy of yours, it's made to take cock. Even big ones like mine!" He said, his tone somewhat of encouragement.

I crawled back between his legs and leaned in. I grabbed it slowly from the base and then started to stroke it softly, watching the foreskin retract, revealing the thick red head. I put my mouth on it and immediately tasted a bitter salty liquid. I looked up at him for signs of approval as I slowly started to suck on him, my mouth was filled in just getting the head in. I felt his hands on the back of my head as he applied some pressure as I kept bobbing up and down. My cheeks were sucked in and I was running my tongue under his penis as I sucked and stroked at the same time.

"Unnnhhh...oh fuck yes...oh fuck....ohhhhh...you sweet little thing...ohhh...ohhh...Mister gonna fuck your little ass deep...ohhh...you're a natural!"

I was delighted that he seemed to be enjoying it. His penis was so different looking from mine and I hadn't been with anyone else, so this was quite an experience for me. It was so thick and veiny. The shaft was white, but the head was reddish and his balls were double the size of mine, like chicken eggs. He was so hairy too. I felt his body begin to shake a bit and at that moment he grabbed me by the neck and pulled me off.

"That's enough for now, time to taste the exotic fruit!" He switched his grip to my throat and pulled me close to him, seemingly with no effort. I straddled him and sat with my legs open in his lap as he voraciously made out with me. He then lifted me up and threw me next to him on the sofa and then turned on to his stomach. He spread my legs open and leaned in to smell my inner thighs before swallowing my dick whole. Unlike in my experience, he did not seem to be in any distress even with my dick all the way in his mouth. But my goodness, did he know how to give oral.