Chapter 9: But wait!

"Thank you, Nina. You're doing very well," as I took her panties from her. Better than I had dreamed. Both her holes looked so inviting in their own ways, I was having trouble deciding which hole to try first. I knew I wanted to degrade her as much as I could right now while she was feeling totally trapped. If I did my worst now and she submitted to it, everything else would be easy.

So I decided to take the "road less traveled" (though in her case neither road was well traveled). I was looking forward to building up ruts in both roads.

She was a picture of forlorn resignation: shaking, trapped in the lion's den, waiting to be eaten. She was naked from the waist down, and was standing with her head down still and her arms at her sides. Her pussy hair was incredibly thin. It was almost downy still. It was also extremely sparse. She kept her legs tightly together, but you could still see a small space between her legs, under her cunt, that allowed light through from the other side.

"Take my shoes and socks off, Nina." She quickly bent down and started to untie my shoes. As she was doing do, I undid my tie and cuffs and started to get out of my shirt. She finished taking my shoes and socks off before I finished with my shirt. I stood up out of my chair as she was standing up, having pushed my shoes to one side. As I finished taking off my shirt, I told her to bend over the desk and grab hold of the other side of it.

"Don't you want to... I mean, don't you want me to take off... my top and stuff?"

"I want to see your tits later. Right now, I just want to fuck you."

"Sir? Can I suck it instead?" then, in a rush, "I'm very good at it. It's just that,... can't we do it in your bed. I'll be very good. I promise."

"Nina. I'm doing this for me, not for you. This is your side of the bargain. Now bend over my desk and grab hold of the other side."

"Sir?... I know I promised not to complain or anything but... can I ask you something?"

"What, Nina?"

"Do you have a... condom, or something? It's just that I don't want to get pregnant, and Luis used one, and you wouldn't want me if I was pregnant, would you?"

"Nina. This is the third time I've told you, and it'll be the last time, bend over the desk. I've told you already that I'll take care of you. That includes making sure you don't get pregnant. NOW BEND OVER THAT DESK."

After I'd practically shouted at her, she jumped back, then quickly scrambled forward and turned toward the desk. As she was bending over it, I could see she was shaking even worse now. She reached out to the stuffed elephant and pulled it toward her face, then she grabbed the other side of the desk with both hands.

Her ass was all I cared about now. I quickly pulled off my pants and shorts, then pulled out a tube of Vaseline that I'd bought at lunch in what I thought was a moment of over-optimistic ecstasy. I stepped up behind her and, after squirting out a generous amount on my hand, I slipped my hand down to her crotch and started to feel her pussy and crotch as I spread Vaseline all over it. I worked some over her slit, but didn't push any into her pussy. I worked my way higher and higher up her crack till I was at her ass. As I started to fondle her ass cheeks and spread Vaseline over her inner crack and ass hole, I started to talk to her again.

"The reason I'm not worried about getting you pregnant is that I intend to fuck you in a way that you can't get pregnant." I slipped my thumb into her ass hole to the first knuckle. I saw her stiffen immediately. "I know you haven't done it this way before, but it wont hurt too bad if you listen to my advice."

She still had her head buried in the stuffed elephant. "Are you listening to me, Nina?" She nodded, though her only other movement was her continuing to shake.

I pushed my thumb further up her ass hole, as I slipped one finger into her pussy. "How does that feel?"

I could see her try to shrug, though that's tough when your stretched out over a desk.

"Is it comfortable?"

Now she shook her head, no.

"Listen to me. I'm doing this for my pleasure, but I don't want to hurt you very much in the process." I pulled my fingers out of her holes and spread a ton of Vaseline over my dick. "It'll be much better for both of us if you just try to relax as I fuck your ass. Don't try to move around. Just let me do what I'm going to do. If you relax your ass hole and let me do the work, it won't hurt too much."

"Do you understand what I'm telling you?" I saw her nod her head into the elephant.

"Are you ready? Is your ass hole relaxed?" This time another attempt at a shrug.

I stepped up behind her and forced her legs apart with my feet. I slid my dick up and down along her slit, then rested it in her ass crack and humped her lightly for a second or two along her crack. Finally, I pulled back and slid the head of my dick down her ass crack until I got to her rear hole. I pushed forward slowly and deliberately.

As soon as the head of my dick started to push into her ass hole, I saw her stiffen and I could see her ass hole try to constrict and expel the invader. "Nina. That's not going to help. If you get stiff and tense, it'll only hurt more... Try to relax and let it happen to you." I could see her body relax slightly as she let out the breath she was holding. "That's right. Just relax." I reached forward and grabbed her hips with both my hands. I tried to rub her ass and lower back as I forced my cock further up her shithole. As the head of my cock slipped past her sphincter, I saw that she started to shake even more.

I didn't even have the chance to get it any further up her, when she reached back with one hand and pushed against me at the waist. She pushed on me till I pulled back and let my dick pop out of her ass. "Stop! Ohhh please stop, sir. You're hurting me." A second later, she had slid off the desk and was lying down on the floor in a heap at my feet.

"Please don't do that, fuck me there I mean. That hurts so bad. I'll do ANYthing, just not that. Please let me suck it... or even... put it in me the normal way. I'll do that. Don't hurt me,... please?"

"Nina," I told her patiently, "I get to do whatever I want to do. You understand that, don't you? That's the deal. Lot's of girls have been fucked up the ass: I've fucked lots of girls up the ass. It's my favorite way. I told you it'll hurt a little bit while you get used to it, but once you're accustomed to it, it'll start to feel good. Before you can get there, though, you've got to just relax and let me do what I'm going to do. If you don't fight it, it won't hurt nearly as much."

"Now," I continued, "our deal was that you'd do as you're told and not complain. You're hardly doing that now, are you?"

"No sir,... I guess not."

"I've told you the terms of my deal, and I've told you to take it or leave it. Now, I'm not going to rape you if you say no to me, but if you want what I've got to offer you, you've got to give me what you've got to offer,... including your ass hole AND everything else. Now, you told me you understood the deal when we out in the hallway. Are you changing your mind now?"

She just lay there for a second and I was afraid I'd blown it AGAIN. Without looking up at me she finally said, to my relief, "No sir, I guess not."

"Don't worry, Nina. It won't be too bad. I'll try to be gentle with you."

I reached my hand down to help her up. She was sniffling and I could see there were more tears starting to form in her eyes, but she let me help her up again and guide her round to face the table. When I pushed on her back to lean her over the table, she understood and exposed her ass to me again. She grabbed that damn stuffed elephant again and tried to bury her face in it and grabbed the far edge of the table with her other hand.