Spanking

Steve called me and told me he wanted a boy that he could spank and then rim. The spanking part didn’t sound too appealing, but the rimming did. I thought it was a good trade off, so I accepted. He also told me that he was really into father/son roleplays.

I cleaned myself off after I took my last final exam and then I drove over to his hotel room. I checked myself a few times in the hallway mirrors before I knocked on his door and rested my weight against the door frame.

The door knob fumbled for a bit and then swung open to reveal a decent looking guy his late 40’s. He wasn’t attractive in any conventional sense but he had that pedophilic look that I sometimes find sexy.

He looked at me and then shivered like he was watching a live sex show. “Ooooh yes.”

I walked in the room and he immeditely went in to rub my cock and grab my ass.

Again he let out an aroused sigh like he had been waiting his whole life to fuck me. His almost desperate hornyness turned me on. I got hard and thanked the universe for giving me such a good client.

“Talk your pants off” he ordered.

I slowly slipped them off. Then he asked me to take off my boxers and socks. I did and again he went “Oooh yeah.”

He sat on the bed and pulled me over towards him. He pushed at my back so that I was bending over. Then he pulled my ass cheeks apart so he could inspect what he was paying for.

“Ooooh yeah.”

I felt his fingers lightly running over my ass, and then I felt his tongue against my asshole for a second. My dick was already oozing out precum.

“Alright little boy, now it’s time to spank you” he said as he adjusted positions. “Now bend over my knee and let me spank your naughty ass.”

Oh yeah, I had totally forgotten about the spankings. Me being over 6′ tall, I felt a little awkward trying to drape myself over his knee. I eventually got into some sort of position, but I think I just looked like a 2×4 that had been broken over his leg.

He rubbed his hand over my ass for a bit and then spanked me. It hurt, but not too bad. Then he spanked again. This one hurt a lot more. Then he spanked my ass over and over again in rapid succession. The staccato spanks felt like my ass was being struck by lightning.

I yelled out in pain and he stopped his spankings for a second and leaned over so he could stick his tongue into my ass. The rimming felt heavenly next to the spankings.

Then he withdrew his tongue and mushed the meat of my ass with hands.

“Such a nice ass you have,” he said. “What a nice round ass it is.”

Then WHAM – he spanked me harder than before. I let out a grunt and then WHAM WHAM WHAM WHAM WHAM – he spanked me over and over again in the same spot. I squirmed around on his knee and reached one of my hands back to protect my bare ass.

He grabbed my hand and twisted it up towards my neck and said “Oh no. This is what your father would do if you tried that.

Then he rimmed my ass for what felt like a microsecond before the spanks returned with vengance. I yelled and tried to free my hand to stop it, but he wouldn’t let me. I yelled at him to stop and he did for a bit, but then went right back on spanking me.

Tears welled up in my eyes.  Then he lifted me up and made me look at a mirror over my shoulder.

“Look at that ass,” he said as he ran his finger over it. “Thats a well spanked ass.”

The color of my ass almost made me want to go to the hospital. It wasn’t just a bright red, it was a purple red, as thick and solid as jelly.

“I never leave any marks behind,” Steve said, sensing my fear. “Now how about I eat that ass?”

I got on the bed and lay face down into a pillow. Steve pushed my legs together with his knees and then pulled my ass cheeks apart. Then his tongue licked at my ass for a few seconds delicately, like a cat lapping up some milk. Then he shoved his face into my ass and swirled his big, warm tongue around as aggressively as he had spanked me.

Getting my ass eaten was amazing. My dick was so hard it hurt. I was hoping this would be the rest of our session, but that wasn’t the case.

“Alright, time to spank you again,” Steve said, bringing my mind back from my rim job trance.

“What? No…NO!” I yelled as he pulled me off the bed, my claws dredged into the bed comforter. He threw me over his knee and spanked me again. I cried out this time and tried to swat his hands off. Again he twisted my wrists up so I couldn’t stop him. I begged for him to rim me, and finally he tired out and threw me on the bed face down.

My dick had gone soft from the spankings, but it re-hardened once I felt his wet tongue. He was calling me “son” and asking me how my dad had spanked me, so I tried to get involved in the roleplay.

“I wish my dad would have done this to me.”

He pulled his face out of my ass and asked “What?”

“I used to wish that my dad would rim me after he spanked me.”

Steve seemed to ponder over what I said for a second, then he burrowed into my ass again.

I felt stupid. God forbid I say anything that sounded incestual. And yes, of course I was just saying that. I’d rather get shot in the leg than have my dad lick my ass.

Steve pulled me up onto all fours and started jacking off my cock as he rimmed me. I felt like I was close to cumming, so I grabbed my cock from his hand and jacked off the final few jacks.

Steve’s tongue in my ass felt amazing as the hot orgasm rushed through me. Every stroke of his tongue was intensified and electric.

I jizzed all over the bed. Once Steve saw that I had jizzed, he grabbed his dick and started wanking himself off.

He started yelling and moaning into my ass as he came. It was kind of hot. Then his head rested in there for a few seconds and I felt nothing but his hot breathe. Then he licked my ass a few more times and got off the bed.

He then payed me and I left.

My first time escorting

People often ask me how I got into escorting in the first place. They think of it as something that only incredibly oversexed or desperate people do – but that wasn’t the case with me.

I had just lost my virginity and I was still nervous about having sex. Along with my anxiety came this strong desire to have more sex so that I could ‘normalize’ it and become comfortable with it.

These thoughts were swirling around in my head one night in my apartment. I was puffing on a cigarette and lying on my bed, feeling a little betrayed by a guy I liked at the time. He never called me when he said he was going to, and that always left me feeling tight in the stomach and edgy.

My parents were financially supporting everything I did, but they kept pushing me to get a job.

I was pondering over these things and blowing out curly smoke rings when an idea popped into my head. I had heard through the news and Dr. Phil that young girls and guys were advertising themselves on craigslist as escorts.

I could do that! I thought, just put up an ad without a picture and see if I get any responses.

I smoked a few more cigarettes and wondered what it would be like to be an escort. Would I fuck people, or just let them suck me off? Would I pussy out and be too afraid to meet anyone? Would I get killed?

I decided that putting up and ad wasn’t exactly the same as actually meeting someone, so I wrote it out. I wasn’t sure what to write, so I mentioned that I was a young college student who had extensive experience escorting.

I wasn’t sure what price to put, so I said $150 for a night. Thats right, a mother fucking night for less than my hourly rate now!

I posted the ad and fell asleep soon after.

The morning I checked my e-mail and, to my complete surprise, I had 50 messages waiting for me.

All of the guys seemed nice, except for the rare few who wanted to piss and shit in my mouth.

They all wanted to see my pictures, so I attached a few modeling photos I had taken three months before. I felt like an idiot a few days later when I realized that my full name had been attached to the pictures.

Some guys called me and told me how beautiful I was and how much they wanted to lick my dick and ass. I didn’t (and still don’t) know what the protocol is for phone calls, so I lay down on my floor and listened to the guys talk. I could tell they were masturbating by their labored breathing – but it didn’t bother me. I liked knowing that guys were wanking off to my pictures.

“Yeah, kid, I wanna cum on your face.”

“Thats fine with me,” I’d say as I clipped my toenails.

“You’re so hot. I wanna fuck that tight ass of yours.”

“Alrighty,” I’d happily answer as I twisted a pencil over my homework.

One particular guy was rather insistent. He told me he was 60 years old, “very attractive” and “sane.” He and I exchanged e-mails over the course of a week.

He refused to give me his number, so our plans had to be made through e-mail. I skipped out on meeting him the first time because I was afraid he was going to bail on me. He called me later on that night, his number blocked, and asked me where I was. I told him that I usually require peoples phone numbers before a meeting, but that I’d make an exception with him.

We planned to meet the following night at a restaurant on the beach.

I was surprisingly calm before I met him. I put on my best clothes, scrubbed my whole body clean and drove off listening to uplifting country radio.

Waiting outside the restaurant, I started feeling nervous. What if he didn’t think I was attractive? What if he was uglier than Orsen Wells?

I heard my fake name being called out and I turned around. Infront of me was a tall, gray haired man smoking a cigaratte. He wasn’t anyone I’d ever be caught dead with under normal circumstances, but he wasn’t hideous.

He and I got drunk and discussed housing prices. I had read before that half of escorting is the emotional aspect – learning how to make people feel good about themselves. So I agreed with everything Bob said and frequently complimented his intelligence and good looks.

Bod was smiling a big, toothy grin the whole time. I could tell I was doing my job right.

After dinner I suggested that he and I take a walk down on the beach. It was late and the entire stretch of sand was empty except for a few vacant lifeguard stands.

A warm breeze was blowing off of the ocean, flipping my hair and flapping my shirt. I pulled Bob up onto a lifeguard tower and started kissing him. He tasted like cigarettes and old hairspray.

As we kissed his hands slid down to my crotch. He rubbed his hands over my cock until it got hard. I was so happy that it got hard – it was completely outside of my control.

Bob kneeled down and unzipped my jeans. He pulled my cock out through the hole in my boxers and started sucking on it like it was the last cock he’d ever suck. I tilted my head upwards and focused on the flimsy roof above me, which bent up and down in the wind and let out a high pitched squeek.

I thought about it, and I didn’t feel that dirty. I was just making money. I was a working boy now.

Bobs wobbly old knees eventually gave way and he fell onto the ground. Luckily he spat out my cock before slipping, or else he would have bitten it off. He looked so pitiful on the ground, I almost felt like mugging him and taking all of his money, but in the end I decided to be the good person that I often am.

I helped him up and told him how I had done the same thing before. My blatant lie seemed to reassure him and bolster his broken confidence.

He looked at my mouth and then down at his cock.

Oh great, now this. I bent down and bit at the shaft of his smallish cock through his pants. Then I pulled it out and started nibbling at the head. Bob moaned like he was having the best sex of his life, and all I was doing was licking the tip.

“Suck on it” he yelled.

I twisted my hand around his dick a few times and then put it all into my mouth with ease. I had told him earlier in the night that I was into S&M (which I am still unsure about), so he tried to make me comfortable.

“You cocksucker, suck on my cock. Yeah, suck on my big cock…..well, not big, but not small either. Yeah, suck on that nice cock…”

Bob’s insecurities shone brighter than all the stars in the sky above us. I let a little laugh out around his cock.

Eventually, I could tell Bob was gonna cum, so I pulled his cock out of my mouth and jacked it off with one hand. I pinched his balls a little with the my other hand because I know that playing with the skin of the balls makes the orgasm feel more intense.

I could feel his dick tighten and pulse as cum squirted out onto the salt-worn  platform. I pulled on his cock a few times to make sure every drop had come out, then I licked the head a little.

Bob, who told me he was a generous tipper, gave me $175.