I'd like to thank Flute 107 for challenging me to make this story better and theMasterBaiter for the later edits and several crucial improvements. I also want to thank Whispersecret for her excellent article on dialogue punctuation.
Although I liked the idea for the story I had no experience with anal sex. I did some online research but took it a step further by trying it with toys. While literally a pain in the ass the story is much more realistic because of the experience.
I really appreciate the help from the very understanding staffs at the local Adam & Eve and Katz stores while buying the toys and accessories I needed.
Finally, a reminder suggested by theMasterBaiter – be sure to read the story tags so you won't be surprised by how things turn out in the end(s) for both characters.
*****
Section 1 – The End at the Beginning
Jessica flew into my office in a panic. "John, you've got to help me!"
"Damn it," I thought. I have to deal with the fallout from the accounting audit and now she has some stupid emergency – this definitely wasn't starting out well for her. "Slow down. What's up?" I asked.
"Remember Roger and the money he took? Well, the investigation is continuing and now they're going to think I took some of it!"
People felt comfortable with me and often came to me with their problems so I knew what to say. "Jessica, you should be fine. They have to prove you did it and they won't be able to find any evidence if you didn't," I explained.
With that her head sank into her hands and she whispered, "That's the problem. I did take some of the money. Actually, a lot. It was a few thousand. I'll go to jail because of it."
I sucked in my breath. This put me in a hell of a spot. I'd just been promoted because my old boss hadn't caught the theft that was being investigated. "If you did it, maybe you should turn yourself in. I'm sure they'll go easy on you," I said.
"N-no, no, they've already started the investigation so it'll look like I was just trying to get away with it. You're the finance guy; you can change things so it looks like Roger took that money too. He's already busted for hundreds of thousands, what's a little more to him? He won't even remember it."
"Do you understand that my butt will be fired if I altered records and got caught?"
"I could go to jail if I get busted," she sobbed. "Please John, I'll do anything. I don't want to go to jail. Maybe I can, you know, do something for you," she said with a scared but hopeful look.
I wasn't quite sure where this was going. Jessica is really cute, about 5'-5", thin but not skinny with small pert breasts that she loves to show off with tight t-shirts and blouses. Her best feature though is her beautiful face, framed by medium length brown hair. She's fun and flirty but a bit vain and self-centered which is likely how she got into this mess. That's something I wouldn't forget even though I could see she was really scared. Besides, I was mad that she was trying to drag me into this.
"Look, this is really serious. No amount of money you can offer is worth my job," I said firmly.
"You don't understand. I know I can't offer you money but I can offer, y-you know, me," she said, pleading with her big brown eyes.
I was taken aback – what was she offering? I was really pissed that she was trying to get me involved but I was interested in what she might offer. "What do you have in mind?"
"I, um, I could do a, you know, a blow, I mean oral sex. Would you help me out?" she again pleaded. I decided to play hardball – I could go to jail to so this should be worth it.
"I can get that for $10 from a professional. I don't think that's enough to risk going to jail for."
Crestfallen, she looked down was silent for a few moments then quietly whispered, "Look, I'll have sex with you."
"What was that?" I asked in surprise. I really wasn't actually expecting her to go that far.
"I'll have sex with you," she said still barely whispering.
I leaned down within a few inches of her face. I could see the moisture around her eyes – she was really desperate. "Do you understand that I'm not involved and I don't want my ass going to jail," I fiercely whispered to her.
Looking at me pleading she said, "I don't want m-my ass in jail either."
That terrible idea was turning into a plan. To this day I can't believe I even thought of doing something like that. Taking a deep breath I pushed ahead.
"Well, is your ass worth keeping out of jail?"
"Y-yes," she said quietly.
"Then maybe you should offer it," I said.
"What do you mean?"
"I mean maybe you should offer your ass," I said firmly.
"Oh no, do you mean sex in, in my butt? Anal sex? That's wrong."
"Yeah, so is stealing from the company. So, that's your choice – I'll risk my ass for yours."
"Please don't make me do that," she whispered with real fear in her voice.
"That's my price – take it or leave it," I said trying to sound like I felt no remorse.
But how could I even say that? When the words came out it was as if someone else was saying them. It was so unlike me. I was the nice guy in the office. But, while Jessica was vulnerable her haughty attitude and the fact that she really thought she could make me risk everything so she could have some spending money just pissed me off.
She stared at the floor, stifling a sob, then looked up with tears running down her cheeks and said, "I hate you but I don't want to go to jail. When do you want to do this perverted thing?"
I gently grabbed hold of her wrists but she recoiled in fear. I said, "Let's do it this evening, your place after work. Be sure to get a good lubricant. Give me your address and I'll be there. And while you're here, let's see what you've got." I reached out and touched her beautiful cheek, tracing the tears running down it. Then she sat immobile as I slid down her neck to her breasts and gently squeezed her.
Reaching down further I moved between her legs. She jumped when I touched her thighs beneath her skirt, and I began caressing her pussy through her panties. Although she remained immobile, her breath quickened as I stroked her warm slit and clitoris that I could clearly feel beneath the thin material.
Leaning forward I kissed her, then leaned into her ear and said, "Tonight, 6 PM. Write your address on this pad, and don't forget the lube." She stifled a sob as I reminded her of what was coming that night.
For the rest of the afternoon I could hardly work. My heart pounded. A thousand times I thought of cancelling the rendezvous, or just having sex, or covering for her without any cost to her, or just letting her take the fall. Why was I doing this? How could I do it? Luckily I didn't see Jessica at all. After discreetly asking I found out she'd left early, shortly after we met in my office. Would she go through with this? Would I? Finally, feeling almost possessed as though I was not really in control of my own body I left my office and went to my car a little early – I had to do some shopping.
I showed up at her apartment at 6:00 sharp with the small bag of things I bought. She opened the door, wearing a loose t-shirt and shorts. She looked amazing. "Come in. I guess we just need to get this over with," she said resignedly.
I asked, "In here or the bedroom?"
"I, I guess in the bedroom. I might as well be as comfortable as possible."
Suddenly gripping my arm, she leaned closer and said urgently, "You won't hurt me, will you? You could really hurt me badly. I'm afraid of what might happen – I Googled it and read that I could get a perforated rectum and die from it. I'm scared John and I really don't want to do this. Couldn't we just have regular sex? I don't have a lot of experience but I can learn," she pleaded.
Was there something wrong with me? "No, your ass is the only thing you can trade for the risk I'm taking. And yes, if someone was rough you could be hurt but I'm not going to do that. I'm not that big and the lube will ease the penetration. You'll be fine – probably sore but this shouldn't be easy for you after what you've done." Sighing with resignation and still fearful, she led me to her bedroom.
"Do you have the lubricant?" I asked. She reached over to the night stand and handed me a small bottle. Looking at it, I noticed she'd bought a small bottle of cheap lubricant. "Jessica, we can't use this. I don't think there's enough and it's not very good."
"Oh, I didn't know. I just went in and bought something then left quickly. I can't believe I messed that up. Will it hurt more?"
"No it won't because we're not going to use this one." I reached into my bag and pulled out a large bottle of premium anal lubricant. This stuff was like buying wine and seemed to cost as much. "We'll use this. It's literally the best one they had." She looked at me in surprise but before she could speak I said, "I told you I'm not here to hurt you. Are you ready?" Still looking a little dazed she just nodded her head.
"OK, I'll take off your pants now," I said as I reached for the waistband of her shorts. I pulled her shorts and panties down together, sliding them down her long shapely legs until she stepped out of them. There she stood before me naked from the waist down shyly trying to cover her brown bush with her hands.
I quickly stepped out of my pants and boxers, freeing my already erect penis. She gasped when she saw it. "You said you were small! You can't shove that in my backside," she said with real fear in her voice.
"I told you I'd be gentle, and I'm not that big. Now, do you want to do this face down or face up?" I asked.
She thought for a second, uncertain as she hadn't thought of that. "I-I don't know. I guess face down."
I said, "OK," and placed a few pillows at the edge of the bed. I then gently positioned her face down over the pillows, with her feet on the floor and her ass sticking up. She was stiff with fear but what a sight! Jessica's incredibly body was there for me, her firm rounded ass cheeks high in the air and her pink slit visible between her smooth thighs. I couldn't help but run my hands over her body.
She stiffened even more as I teased her swollen clitoris and slid my hands along her plump labia. She flinched when I slowly parted her and slipped one finger into her body. She was surprisingly wet. As I continued to finger fuck her I felt her relaxing. She probably thought I'd changed my mind but the whole time I was focused on the inviting crack between her pale cheeks.
