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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 illegal bahis 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 illegal bahis siteleri 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.
“Ok, I promised I wouldn’t hurt you so I bought something else.” Curious, she turned around as I pulled an Adam & Eve Booty Camp training kit from my bag.
“What is that?” she asked hesitantly.
“These are three different sizes of anal plugs. I did some research to make sure we did this right. We’ll start with the smallest so you can get used to it and we’ll slowly work up to the largest size which is about the same as me.” I looked into her worried eyes and said, “You did something very bad and you asked me to risk a lot. But I’m going to hurt you.”
I could see the relief in her eyes. “Thank you,” she said softly.
“Wait here a moment while I get these ready,” I said, then went into her bathroom and carefully washed the brand new training plugs. I could see her on the bed as she watched me. “Ok, all done. You ready?” She grunted in acknowledgement.
“Spread your legs a bit, it’ll make it easier,” I said gently. Taking the bottle, I spread her cheeks with one hand and watched her puckered little opening convulse. She gasped as the cold fluid poured onto her body. Keeping her cheeks spread I reached out and touched her hole – I could hear her gasp as she jerked forward. I asked, “Everything OK?”
“No. No one’s ever touched me there. This is so humiliating,” she stammered.
“It’ll be OK. It’ll make amends for stealing that money.”
“I really wish I’d never taken that money,” she whispered.
Liberally covered in lube, I slowly pressed the smallest plug into her backside. Her breathing quickened as I pushed the small plug into her, spreading her little hole to accommodate it. I was surprised at how easily it slid in! “How are you doing?” I asked.
“O-ok,” she replied.
As I gently slid the plug deeper I watched in fascination as her anal opening expanded with the plug. When the widest part was just sliding in the plug suddenly slid out of my fingers and penetrated until the flared base was hard up against her backside. Jessica gasped and bucked, and let out an involuntary cry of … pleasure?
“You OK?” I asked.
In a ragged voice she said, “Yeah. That feels so weird.”
I gently stroked her smooth backside and leaned forward. “Weird as in good?”
“Ummm… maybe,” she said between panting.
I grasped the base and slowly, teasingly pulled the plug back. Jessica began to gyrate her hips as I worked the small plug in and out of her little opening, pushing the lubricant deeper and deeper. Inside the bedroom the only sounds were the ticking of a clock, the soft wet sound as I penetrated her and our ragged breathing.
“Are you ready for the next one?” I asked.
“Yes, no, I don’t know. It’s not as bad as I thought it would be.”
I slowly pulled the small plug out of her. She bucked again as her sphincter tightly clung to the well lubricated plug being withdrawn from her butt. Setting it aside, I grabbed the middle size plug and touched the tip to her now tightly closed anus.
It was a repeat of the smaller one, only the reaction was stronger. She cried out as her body took the widest part and pulled the plug up into her. In a few moments she was bucking back and forth as I slide the anal plug in and out past her tight sphincter muscle.
My cock was straining as I teased Jessica with the plug. After a few moments I asked, “Are you ready for the big one?”
“I guess so,” she said raggedly. Was there a little excitement in her voice?
Seeing now how to excite her, I made sure I withdrew the middle size plug very slowly. The careful attention was paying off as Jessica panted with pleasure. As I withdrew the plug I saw again that her anus smoothly closed, remaining open only for a split second as I pulled the tip out of her. I set the middle plug down and grasped the biggest one.
“Do you want me to put some more lube in?”
Jessica nodded, so I pushed the bottle against her opening and gave a good squeeze. “Oh shit, yes,” she moaned, and then turned back to me embarrassed. “I mean, please use more lubrication,” she said blushing deeply.
“Well, you sound ready. Here it goes.” Jessica tensed as I pushed the tip of the plug against her still tiny opening and slowly inserted it. I could see Jessica tighten up even more and hear her breathing become more canlı bahis siteleri rapid as I slowly slid it into her. Surprisingly, just as the widest part of the plug was entering her I encountered a lot of resistance and Jessica gasped.
“No, no, stop for a second,” she managed to get out.
“Ok, I’m stopped. There’s just a little more but it’s the biggest part.”
“I don’t think it’s going to fit!”
“I’ll pull it out and put more lube in. That should help.”
From reading the reviews on the plugs I figured this might be a problem but if we couldn’t get this one in I wouldn’t fit either. Jessica gasped again as I slowly, very slowly, pulled the plug out and slowly pushed it back in while wiggling it. I think she was enjoying this! As the last of the plug came out her opening smoothly closed until with a very slight pop it came out. I spread her cheeks with one hand, inserted the lube into her exposed hole and squeezed.
“Oh shit! That feels cold.”
“Sorry, I was trying to get it in there.”
“It’s OK now.”
I figured the more the better so I continued spreading the lubricant all around her opening. She squirmed as it started dripping down her thighs.
Dropping the lube, it wasn’t long before I slowly pushed the plug against her tight anus and began working it in, back and forth, side to side. Jessica’s moaning and movement told me she was really enjoying this. I reached around her left side and underneath her with my free hand to massage her clitoris, which really got her moving. But no matter how carefully I worked it I couldn’t seem to get the big plug all the way in. I was getting frustrated but I had to be careful – I really was afraid of hurting her.
Working back and forth I pushed a little harder which elicited a cry from Jessica. “It’s not going to fit!” she said breathlessly.
Sternly I said, “If this doesn’t fit, I’m not going to fit. And if I don’t fit I’m not going to be happy.”
“I wish I hadn’t taken that money. Just, just push it in slowly, I’ll try to relax.”
I really didn’t want to hurt her but this needed to happen. Working back and forth, with more lube, and playing with her clit I pushed it just a little deeper each time. Jessica groaned and gasped. It was hard to tell from pleasure or from pain but she wasn’t yelling stop yet.
I drew the plug back about a half inch then pushed it back in using more force. Jessica’s head jerk upward and her whole body bucked as she let out a short cry. Suddenly the widest part of the plug disappeared inside Jessica and her sphincter muscle quickly swallowed the plug until the base rested against her cheeks. “Oh god, oh god, oh god,” she cried out.
I waited a moment for her to catch her breath.
“It’s in – your behind just pulled it out of my hand. Everything looks OK.”
Still breathing rapidly she said, “It’s so big. I can’t believe you pushed that in me. “
Eager to keep going I said, “I’ll just slowly work it in and out a bit.” I moved it back and forth but not all the way out since her anus enlarged alarmingly when I pulled the largest part near her opening. She finally got a little more used to it, so I dared to pull it out a bit more.
“Oh, oh, oh!” she panted as it stretched her on its way out. I’m not quite sure why but I figured I should push it back in before she squeezed back. I slid it slowly back in, and before her ass could pull it back in I slowly pulled it back out, back and forth a few times. From the “Oh, yes, no, yes, oh shit!” she kept repeating I was guessing this was giving her an intense mix of pleasure and pain.
“How are you doing?”
“Shit, shit, shit. OK, just stop for a second,” she was finally able to say. I stopped with it partially withdrawn and briefly relaxed my grip. In that split second the lube slick plug slipped out of my hand and her sphincter rapidly pulled it in, drawing a loud, “Oomph!” from her.
“Ooh, sorry, I lost my grip. Do you want me to take it out? Once it’s out you’ll be ready to take me.”
Grunting, she said, “Yeah, just… pull it out.” I slowly pulled it back out, hearing her sharp intake of breath as it stretched her to maximum, then the huge exhale of relief as it got smaller and finally out. Excess lubricant flowed out of her rear and down her thighs. I reached for the tissues by her bed and cleaned her up while she stayed in position just breathing hard.
After a few moments she sighed and resignedly said, “I guess I’m ready. I can’t believe I’m going to do this.”
“We’ll take it slowly and carefully. Just relax”. I spread more lubricant into and onto her as well has on my engorged penis. I worked patiently to make sure I did it right. Grasping her cheeks with both hands I spread her wide, fully exposing her now slick little opening. “OK, I’m ready. Here it goes.” Her whole body stiffened again and her breathing became very rapid as my raging hard-on touched her opening.
Now she was getting nervous. “John, I’m not sure I can do this,” she whispered and pleaded.
“It’s too late for that,” I tersely whispered back as my penis began pushing open her tight sphincter. She started moaning as my head widened her hole ever larger and pushed ever deeper into her back door, again violating a privacy she thought was sacrosanct.
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