Escort: Anal Training Day

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I was still sound asleep when my cellphone rang at 11:00 am. It was BJ.

“So what time did you get home last night?” He was trying to sound upbeat…dude knew I took a late call for him, and he knew he’d be waking me up.

“Well BJ, it wasn’t last night; it was 7:30 this morning. The client wanted me to spend the night.”

He liked hearing that. “So, how much did he pay you?”

“I know we are supposed to charge $1700 for an overnighter, but after he paid me the first $600, he only had $1000 left. I agreed to stay for an additional $800.”

Like any pimp, BJ was pissed. “Well, are you gonna cover the $300 out of your share? I ain’t running a fucking charity here.”

He was trying to play the role of tough guy pimp, but I knew him well enough by now. He didn’t scare me at all, and I wasn’t gonna take any shit off him.

“Oh fuck you BJ. I turned a $600 call into $1,400. Instead of making $300 off “my ass,” you’re getting $700, so stop complaining.”

He still wasn’t satisfied. “Hey, you left him with $200 in his wallet. You’re too fine to be giving it away. Next time you clean him out. These mother fuckers always got more money…don’t let them play you

Christ, he had a way of pissing me off. “Okay, look…I took good care of your client. When he comes back, he’s gonna ask for me again, and he’ll wanna spend the night. You gotta be thinking about returning customers. I’m gonna make a lot of money from him.”

He wouldn’t let it go. “That’s right Emma. You been doing this for 3 weeks, and you wanna tell me how to run my business. Next time you clean the mother fucker out.”

“Yeah, yeah, yeah. Okay…it will never happen again. Why the fuck you calling me so early?”

I heard him giggling at the other end, and he said, “Well, that sounded more sarcastic than sincere. Anyway, I gotta day call for you. You have to be at a luncheon at the Marrakech Hotel at 12:30 pm. A regular client will meet you at the concierge desk. His name is Jack Patane. He knows what you look like. It’s gonna be lunch and then go to his room and fuck him. He’s paying $800.

Oh great…I got 3 hours sleep, and now I gotta get showered, put on make up, find a dress, find the hotel, find him, and I have 90 minutes. “BJ, what the fuck?”

More giggling…”Oh, stop complaining. Trust me, you’re gonna like this call, now shake your ass and don’t be late.”

I guess I shouldn’t complain, but I loved giving my pimp the bitch act. The escort job was working out real well for me. I was putting a lot of money in the bank, and aside from a few problem clients, I actually enjoyed the guys. I quickly showered and douched, put on some eye makeup, dressed, and was out the door in 45 minutes.

I actually made it to the hotel 15 minutes early, valet parked, and found the concierge desk. I sat down to wait for the client, wondering what he would be like. I was imagining an older white guy, with a pot belly and bald head, when a black guy came up to me.

“Hi, I’m Jack, and you must be Emma.”

I was speechless…”Yeah Jack, I’m Emma.” I extended my hand and he helped me up. He must’ve sensed my surprise, and he asked me if BJ told me he was black.

I stammered a bit…”No, he didn’t, but that’s cool. I’m good.”

He was tall and muscular, with close cropped salt and pepper hair. He looked like he might have been a professional athlete in his younger days. He was wearing a navy blue golf shirt and dress khaki trousers, so, having dressed casual, I was somewhat relieved.

As we walked to the ballroom, he explained the luncheon was an annual event for college football coaches and officials…just an informal get together/meet and greet held at the beginning of each season. The next two days they would be holding seminars on rules changes, injury prevention, and new training methods.

He told me he and his wife were not getting along well but we’re staying together until the children were old enough to go out on their own. He commented that I looked like I worked out, and when I told him I was into weightlifting and crossfit, he said, “Okay, that’s our cover story. You are a personal trainer who took my class a couple years ago at State College.”

I smiled, “Okay, but aside from knowing where State College is, I’ve never been to the campus. What if someone starts asking me about people I know, and where I worked and all that?”

“Oh, don’t worry…just BS your way through it. People who ask these kinds of questions aren’t interested in the answers bahis firmaları anyway. You’ll be fine.”

We were seated at a table with eight other people, but only one other couple. He was an older guy, and the woman he was with was about my age. She was wearing a large diamond ring though, so I assumed they were married. The luncheon was interesting, and I love football. Some of the people in attendance looked familiar, like I had seen them on TV. Afterwords, we mingled a little, and I played the “Jack’s personal trainer girlfriend” role without a hitch. People were starting to leave when Jack asked me if we could go up to his room.

We rode the elevator up to the seventh floor and found his room. I sat down on the bed while Jack used the bathroom, and when he came out, he was wearing the hotel’s robe.

He sat down next to me, and handed me $800 without speaking. I stood up to get undressed, and he must’ve sensed I was nervous.

“Emma, have you ever been with someone like me before?”

I shook my head, undressing as I spoke, “No, but that’s okay. I’ve been wanting to try for sometime now. I want you to know, I’m really attracted to black guys, but up until now it hasn’t worked out. I mentioned this to BJ once, and I think this is his way of surprising me or “breaking me in” if that’s how to look at it. But hey…have you ever made love to a Filipina?”

That caused a chuckle, and he said, “No. Never been with a Filipina or Asian for that manner. Only white and black girls…this is a first for me too.”

That put me at ease, and I turned away from him and asked him to unhook my bra. I shook it off, letting it drop to the floor, and slid off my panties. Then I turned to show myself to him. It’s kind of a little thing I do. The look a man gives when he sees you naked for the first time is what I live for. I played with my tits and nipples, twisting and pulling, then I showed him my sex, first from the front, thrusting my pussy and inviting a touch, then I turned and showed my ass, tracing a line from my clit up my crack and back.

He touched me when I did that, lightly flicking my bean, and he ran his finger up between my cheeks, pausing to press on my anus. Then he fondled my ass. I turned to face him again, and he stood up, opening his robe. His slender 8 inch penis was erect, and I was surprised to see he was shaved clean. He took me in his arms and we embraced and kissed. I stroked his manhood while he played with my ass, again pressing on my butthole.

We ended up on the bed, and I took him in my mouth, gagging myself on that beautiful black tool while he finger fucked my cunt. He was driving me crazy, hitting my g-spot with those long thick fingers.

I stopped sucking him for a moment and jacked him off as I used my tits on him, dragging them across his genitals and belly. I wanted his cock to squirt in my mouth, and when he started eating my pussy I resumed blowing him, rubbing his glans and male g-spot against the roof of my mouth.

I soon had him where I wanted him, thrusting wildly, and he ejaculated with powerful throbbing and an explosion, choking me with that flood of thick cum. I sucked that cock dry before collapsing on him.

“Wow Emma, that was a blow job to remember…love what you did to me with those titties. God, that felt good.” He pulled me up next to him and gave me a quick kiss after wiping a droplet of sperm from the side of my mouth with his finger. I excused myself and went to the bathroom…

“Hey Jack, mind if I use your toothbrush?”

“No Em, help yourself.”

After I brushed my teeth and freshened up, I returned to his bed. We cuddled a bit, and I mentioned we still had sometime if he had something else in mind. I was playing with his dick, and he was starting to engorge again.

Jack stroked my hair and mentioned there was something he was interested in.

“Emma, BJ told me you’ve never had anal sex. That interests me a great deal…if you’ve been thinking about giving it up, I’d like to help you with that. It’s kind of a specialty of mine, introducing girls to the pleasures they’ve been missing. I have everything I need with me to make this as pleasurable for you as possible…just need your permission.”

That fucking BJ. He was jealous that I had sort of promised to let Richard take my anal cherry. He knew I was wanting to give it up, and he knew Jack was the right man for the job if he couldn’t do it himself. He also knew Jack would pay, and he would get a cut. So my ass gets deflowered, he makes kaçak iddaa money, and Richard ends up in fool’s paradise, thinking he has fucked an anal virgin when I finally let him do that to me…what a conniving asshole. Oh well, it is what it is.

I snuggled up to Jack, “Yeah, I have been wanting to try that with someone who knows what they’re doing, but i’m a bit afraid. Will it hurt? I mean I trust you, but if I say stop, will you back off?”

“Of course Emma. I am a gentleman, maybe a perverted gentleman, but a gentleman none-the-less. I you say stop, we stop.”

I was satisfied that he was the man for the job, so I brought up the subject of money…”How much will you pay, Jack?”

“I asked BJ about that, and he said $500 extra. Does that sound okay?”

Figures that pimp would have it all figured out.

I frowned and said, “Well, here’s the deal…I’ll tell BJ you gave me $500, and you back me up, but if this is going to happen, it puts me in a bad position with BJ’s partner Richard. He’s the closest thing I have right now to a boyfriend, and I sort of promised my cherry to him. Whenever we fuck, he always finger fucks my ass, like he’s preparing me, so he knows me pretty good. If he senses that someone beat him to it, he’ll be pissed. So, I want $650. Just tell me what I have to do.”

“Okay, deal, and I promise you’ll be happy you trusted me with this. And Richard will be none the wiser. First thing we do is give you a couple of enemas, one right after the other. I want you cleaned out good. It will make it a lot more comfortable and less embarrassing. Have you had a bowel movement yet today?”

“Yes, I’m very regular, and I take a daily protein-fiber shake every morning instead of breakfast, so I should be good.”

Jack told me that he would just be using warm tap water on me for the enemas…maybe about 6 ounces, and he showed my a rubber bulb with a four inch stem that was about ? of an inch in diameter. The stem would be inserted inside of me, and he would squeeze the bulb, expelling the solution. I would feel an urge to shit in a few minutes, and then we would repeat the process. After I voided my rectum a second time, I would be ready. Then we would started the anal dilation process which would involve well lubricated digital penetration. He sounded like he knew what he was talking about, which was a relief for me.

Before we started, I sat on the toilet and tried to have a bowel movement, but only managed a couple of small farts. I washed myself and went to the bed. Jack put me on all fours and told me to lay my head down on the bed. With my ass fully exposed, he applied a liberal coating of KY Jelly to his index finger and to my anus and slowly penetrated me. Remembering what Richard told me, I tried to push him out. He recognized what I was doing and mentioned that it appeared I had done some homework.

He continued to use his finger on my ass, and with his other hand he massaged my vagina, occasional penetrating me there too.

“Emma, you are really tight back there…try to relax as much as you can. You muscle tone is excellent, I feel a strong sphincter muscle, and that is good. You should recover with no trouble.”

I couldn’t converse with him with all that was going on. I felt totally possessed and controlled by this man. I could only answer with a lame, “Uh huh.”

He withdrew from me and then I felt the tip of the enema bulb enter me. It was hard and not very pleasant compared to his finger. When he squeezed the warm water into me, it felt very odd. It seemed like an awful lot of water.

Jack rolled me over when he finished and put a towel under my butt.

“Okay Emma…hold that in as long as you can. When you feel the urge, i’ll help you to the bathroom. You do your thing, and I’ll fill you up again.”

I was feeling really bloated, and when I had to go, I made my way to the bathroom, bent over with Jack helping me. I barely made it to the toilet and expelled everything in one big gush with some very audible farting.

Jack helped me to the tub and washed me. I went back to the bed and assumed the position. Ever so attentive, Jack made sure I was properly greased and filled me a second time. By now, I was really looking forward to the actual penetration, and I was relaxed while he played with my pussy. After about twenty minutes, I made my way back to the toilet and voided for the second time. This time I wasn’t the least bit embarrassed about the disconcerting sounds coming from my ass. Jack was wearing his robe, kaçak bahis but it was open in front and he was hard. This whole ritualistic ass thing was really turning him on.

This time he carried me back to the bed and lay naked beside me. He sucked on my nipples until they were about to burst. He finger fucked my vagina, wetting me good and then put me back in the submission position. He took a clear plastic syringe that was about six or seven inches long and perhaps twice the diameter of the enema bulb and filled it with KY Jelly. After lubricating me, he inserted the syringe deep inside me and pushed out the lubricant as he withdrew it. Then he put me on my back and performed cunilingus, teasing me until I begged for his cock.

He positioned himself between my legs and entered me slowly. While we fucked, he massaged my anus, penetrating it slightly with the tip of his middle finger.

“Okay Emma, you tell me when you’re ready. When you give the word, i’ll put you back in the enema position and we’ll get this done. While I fuck you ass, you masturbate, and we’ll see if I can get you to cum.”

I was more than ready, “Now Jack, now…fuck my ass, fuck it good.”

Jack put me in the position, and I held my breath as I felt the tip of his cock pressing against my asshole. I was about to tell him, “Now,” when he entered me in one steady slow thrust. I screamed and pounded my fist into the pillow. I felt like I was being split in two. He was motionless for a moment and then he pulled out, leaving just the head of his dick in me.

“Okay Emma, this is really happening. Now push me out.”

He began to slowly push back into me, and I tried to push back. This time it wasn’t nearly as painful. He withdrew and thrust into me a third time, and I was ready for him. We got into a rhythm, and I began to masturbate. I finger fucked myself, and felt his cock as it fucked my ass. He held my hips firmly, keeping up a steady, slow pace. Any pain I was feeling was replaced with minor discomfort, and I started to move my ass. I knew I was pleasing him, and that made me want to fuck him harder. Jack responded by holding me with one arm around my waist and played with my tits. I imagined that my pimps were watching me, and jacking off. I imagined that all my former boyfriends were watching me, wishing that they were the person in my ass. I imagined that my high school teachers were watching me, especially the perverted math teacher who was always looking up my dress, and I imagined I was a porn star with fans all over the world., while I was lost in my fantasy, a sudden orgasm engulfed me. I kicked my feet, bucked my hips, and screamed into the pillow which triggered Jack’s climax. I felt every drop as his semen spewed deep in my ass. We collapsed together on the bed, and Jack remained inside of me until his erection subsided.

When he finally pulled out and rolled off of me, I felt like I was going to have a bowel movement. I scampered to the bathroom, letting out wet farts on the way, but it was a false alarm…just a lot of air. I washed myself and soaped up a wash cloth for Jack. He lay there motionless while I cleaned the cock that took my cherry. I dried him, and we cuddled briefly. Jack finally broke the silence.

“Well Emma, how was that for you? Any regrets? Are you okay?”

I kissed him hard on the lips, “No, no regrets at all. This has been quite a day…I should pay you. My first black lover. My first anal experience. You did it all, and you did it so well.”

He kissed me back, “You were magnificent, a true sex goddess if ever there was one. I’ve got one request though…would you let me take a cell phone picture of you? I’d like a selfie of me and your ass, and then a separate picture of just you.”

I laughed, “Well, okay I guess…you want to memorialize the damage you did to me? My asshole is still stretched open. Just promise me I won’t see this on some website.”

“No, no…we won’t even show your face, just your ass with me posing with it and then one of you lying on your belly with your legs spread. I’ve taken a lot of virgin ass, and you were the best by far. I want to be able to remember this, and I’m gonna be jacking off to you for quite a while.”

I giggled at that…”Well, if you want the real thing, you know how to get a hold of me. I’d love to see you again. And I don’t mind you getting my face on these. Just be discreet.”

So Jack got his pictures, goddamn my asshole was stretched big, and I got my money, and he promised to call me next time he was in town. It took another day before my anus was back to normal, and it felt different, very different. I was hoping Richard would not notice when he finally got around to taking my “virginity.”

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