Desperate Ch. 08

1. A New Direction

I tried. I did; I really tried. But Jake, he's a big guy. And as much as I wanted to see what he felt like up inside my ass, it just hurt too much. I bit the pillow, I screwed my eyes up, I stifled my screams. But it hurt. It fucking hurt, and I had to beg him to stop.

"Please, Jake, please stop. You can stick it up my pussy as hard as you like, but please don't try any more with my ass. It hurts so much!" I sobbed.

"Oh, I'm so sorry, Tori. How about this?"

I yelped when he changed the angle and shoved straight into my cunt in one deep, brutal thrust. It was so fierce, he carried me up the bed. And he pounded away, really hard, fast and deep. Maybe I was a little drier than usual, perhaps because of the pain earlier, but although it was exciting at first, after a few minutes I started feeling sore.

I wanted to come, but I felt sure that I'd get too tender inside before the G-spot pressure became enough, so I slipped a hand under myself and teased my clit. Even then, I wasn't sure.

"Fuck, baby - you're - you're punishing - punishing my poor - my tight little cunt!" I moaned, breathlessly. "Have - have mercy - on this - this poor slut!"

"Just take it, whore!" he growled in my ear. "Take all of my dick, right up your slutty little cunt, you dirty fuck-toy!"

OK, so I liked a bit of dirty talk, but this - and the sheer brutality - was a little too much.

"Easy, baby - please? I wanna - wanna feel - feel your cum in my cunt, but - but please, have mercy - mercy on your little slut! PLEASE?"

But he didn't slow his pounding, and a few moments later, I heard him moan and felt him pulse inside me. Fuck! I wasn't even close; my cunt was feeling sore and he'd come. A few moments later, I felt him slide out and roll away from me, panting.

"Hey baby," I said, trying to be conciliatory but feeling pretty pissed, "what was that about?"

"I - I dunno," he said in a weak voice. "I just had a shit day, and - and I guess I needed to - take it out on someone. I thought you liked it hard and dirty."

"Well I do, baby, but that was kinda brutal. I think we need a safe word, so you can stop if it hurts too much."

"Maybe. I so wanted to get inside your ass. Could we try again?"

"No, I'm sorry. Not anytime soon, sweetie, I'm afraid. See, your cock's very big, and while it usually feels good inside my cunt, my little asshole is just too tight."

"We could, like, stretch it some more with - I dunno, some beads or a plug or something."

"Maybe. But right now, I'm sore and I need to come. Would you go down on me, please?"

"I - sure," he said, but he sounded reluctant. He went down on me for a while, but I felt he wasn't trying. He just focused on my clit, and barely moved around my pussy.

"Hey baby, try a little farther back," I said, trying to guide him.

"Mm, no, sorry. My cum's leaking out of you."

"And?"

"I don't like to taste it."

I sat up. "What? So it's OK for me to get a huge mouthful of your jizz, but you won't lick me after I've tried to give you my ass and let you fuck me brutally and come before me, because you might taste some of your own? What the fuck?"

"It seems kinda - gay..." he said, weakly.

I laughed.

And then he hit me. He smacked me around the face.

For a moment, I was shocked. And then I just rolled off the bed, pulled my dress back on, grabbed my panties and purse, checked around and headed straight for the door.

"Baby - please, no! I'm - I'm sorry - I - I didn't..."

I didn't hear any more because the door slammed behind me. I hit the Uber app as soon as I was out of the house and started walking. All the while I was crying. I was some way along the road when he came running after me.

"Tori, baby, I'm sorry. I - I didn't mean it..."

"Leave me alone!" I almost shouted as I pushed him away and kept on walking.

And at that moment, as luck would have it, a cop car pulled up beside us. Jake backed off.

"You OK, lady?" the officer said through his open driver's window. "Is that guy bothering you?"

"I - I - my boyfriend just hit me, so I just had to leave his house. I'm - I'm waiting for an Uber."

The cop got out and approached Jake, who looked sheepish. "Hey, you! Did you hit this lady?" I could see the cop fingering his gun.

"Officer," I said, not wanting this to turn ugly, "It's OK. I - I just want him to leave me alone so I can get my ride home."

The cop turned to me, still glancing back at Jake, who was holding his hands up and backing away. "I see. Would you like to file charges? If you want, I could arrest him for assault."

"No. No, it was - it was just the once. But - but I'm really upset. You see, I thought he loved me, but..." I broke down again.

"I'm real sorry to hear that, lady." He turned back to Jake. "Yeah, you heard her. Back off, asshole!"

He turned back to me. "I hate anyone who hits a lady. If you change your mind, just call the station and we'll get on around there."

As we were standing there, my ride arrived, so I was able to get away without further trouble. When I finally arrived home, I went for a shower, had a couple of whiskies - I don't usually drink hard spirits but I needed something - and finally went to bed. I felt utterly miserable for the first time since my 'transformation' had started. I'd found a guy who I'd thought was just right for me. We'd been together for maybe three weeks. The sex was great, and I thought he cared, to the point where I was prepared to offer him my virgin asshole. But it seemed that, underneath, he was simply an aggressive asshole.

I slept, but not well. The heartache of having my boyfriend turn out to be a violent jerk kept me awake. The next day in the office, I checked my phone. There were maybe a dozen texts from Jake, apologizing and begging me to call him. And yes, part of me wanted to. I'd never had a real boyfriend before, and certainly nobody as good-looking and financially solvent as Jake. But part of me thought that if, just because he'd had a bad day, he could slip into being a violent bully when we were just fuck-buddies, what would it be like if our relationship became closer and I started to depend on him? It was horrible, and I was upset and confused.

I thought about talking to Mr. Rogers about it, but he'd told me in pretty clear terms that we shouldn't have any more sexual contact, and I guessed that talking about my relationship with Jake, and what had sparked the problem - our failure to have anal sex - might get him angry. And I'd cried on his shoulder before, when I'd first confessed that I was a virgin, so I just kept quiet.

And anyway, he seemed busy and distracted, so I just got on with my work. It seemed that every few minutes, my phone would ping with a new text message. I'd blocked Jake's calls after the first two or three times he'd tried to speak to me. I finally texted him back, telling him to leave me alone. I said I'd call him once I'd had a chance to think about things.

But isn't it weird how fate kinda throws the dice? Sometimes you get snake-eyes, sometimes a double six. Well, it was a Friday and I'd had to work extra late in the office. Mr. Rogers had gone home early and left me with some important correspondence that needed to be in the post by the weekend. It took longer than either of us expected, so I didn't leave the office until after six-thirty. I was coming home on the bus, and we were just passing a diner I'd visited once or twice, when I noticed Mr. Rogers' car was parked outside it. I was curious - and hungry - so I got off and peered in through the window of the diner. I thought maybe, if I could talk to him outside of the office, I could explain and he could help me.

But my thoughts of a quiet conversation with my boss evaporated almost immediately. In a booth opposite the door and slightly to the right, I could see a man who I guessed could be Mr. Rogers. Sitting opposite him was a woman I recognized from the photo on his desk - his wife, Jennifer. I thought she was pretty, in an older, more sophisticated way, and it was obvious why he didn't want to jeopardize their marriage. But I could see she wasn't happy.

Then a greeter came out and asked me if I wanted to eat. I followed her inside, taking care not to be seen by Mr. Rogers, and when the greeter tried to take me to a table further from the door, I asked if I could have the booth that backed onto the one where Mr. and Mrs. Rogers were sitting. "I - I have some important papers I need to go over, and they're kinda sensitive, so I'd like to sit somewhere very private."

"Well, we have several booths if..."

"No, that one will be fine, thanks. And could I have a Diet Coke, please? Oh, and I know what I'd like to eat; a chicken Caesar with the dressing on the side, please." I didn't want my voice to carry to the next booth and for Mr. Rogers to recognize me. I smiled at the girl and sat down in the booth, my back to where my boss was sitting.

I started listening to snippets of conversation from behind me.

"Jennifer, baby, there honestly isn't anyone..."

"Tony, you've always been a very bad liar. I can tell when you're lying, so don't try to fool me. Who is she?"

"There is no she," I heard him protest.

"Oh, so it's a boy, is it? Have you finally realized you're gay?"

I could hear the anger in her voice.

"Jenny, please! There isn't anyone else. There's only ever been you. I wouldn't do anything to jeopardize what we have. You and the kids are the center of my world."

"I thought I could trust you, Tony. But you just keep lying to me..."

"Jenny, baby, please don't let's fight over this, and not in public. Come on. Let's go home and have a drink and be - be us again." His voice sounded almost pleading.

"No, Tony, I'm not leaving until you've explained your behavior."

"Jenny - look, baby, I'm leaving now. Get up and we can talk some more at home."

"No Tony. I want answers, and I want them now."

"Jenny, I'm leaving this diner right now. Come with me. Don't make a scene."

"No. Go if you want. I'm gonna sit here and think. Or you can stay and explain yourself."

"Jenny, there's nothing to explain. Like I said, I'm going home. Here. That'll cover the meal and the tip. Now get your purse and come out to the car."

"No. I'm staying, and so should you."

"Well, if that's what you want. Here's another twenty. Get an Uber when you're ready, but I'm leaving now!" His voice had taken on a harder edge.

With that, I heard him get up. I turned, peering around the edge of the booth, and watched him storm out of the diner. From the other side of the booth, I could hear someone sobbing.

I don't know what made me do it, but I grabbed my purse and my Coke, stood up and went around the end of the booth.

"Hey, ma'am. I'm sorry, but I couldn't help but overhear the argument you just had with - with your husband?"

She nodded. Tears were running down her face.

"I - I've just had a big fight with my boyfriend and could use some company. Would you mind if I joined you? Maybe we could share stories, make each other feel a little better?"

She gestured for me to sit down. I held out my hand. "I'm Tori, by the way."

She took my hand in a rather limp handshake. "I'm Jennifer. Jenny," she sniffed.

Just then the waitress arrived with my salad, looking a little puzzled. "Sorry, I decided to join this lady who's not feeling too great. I'll sit here if you don't mind," I said, taking up the seat vacated by Mr. Rogers. "I think this..." I indicated the cash on the table, "is to settle their check. But I think Jenny here would like another drink. Jenny?"

"Er - er, yes. A - a Margarita, please."

"Sure," I said. "I'll just stick with my Coke, thanks."

The waitress collected the pile of bills and headed off.

"So Jenny, it sounded like you think your husband cheated on you. Men are such shits, aren't they? I was having a great time with my boyfriend, but then he just had a bad day and he hit me for no reason. But from what I overheard - please excuse me, but I couldn't help it - your guy kept saying he didn't do it. Maybe he didn't. What makes you think he had someone else?"

"Well," she sniffed, "he just - I don't know. A few weeks ago he started behaving strangely. He'd come home late from work, and he'd be evasive as to why. I was sure I could smell a woman's cologne on him, but he said it was just some air freshener they'd been using at the office. I was sure there were semen stains on his pants one time, but he said it was just glue from somewhere in the warehouse. And he's always been a terrible liar, so I can tell he's hiding something." Tears started running down her face again.

"Oh, I see. Do you have any suspicions? Like, who do you think it might be? Does he have a - a secretary?" I was taking a big chance here.

"Oh no, it couldn't be her. She's a mousy little thing in her forties. Overweight, quite plain. He wouldn't be interested in her. See, I don't think it can be anyone at work, because almost everyone younger than Tony is male. Unless he's suddenly decided he's gay."

"That's not likely, is it? I mean, I guess you've been married for quite a while. Has he ever shown any - er - tendencies like that before?" I knew Mr. Rodgers was utterly straight, but I couldn't say that.

"No. But - well, what would you think was going on if you had suspicions like mine?"

"Well, I don't know your husband, but it could be something innocent. I mean, do you have any actual evidence that he's done anything bad? You know, like hotel receipts or women's underwear in his pocket or stuff?" I knew there would be none of this, so it was a safe steer in the conversation.

"No. Nothing. Normally I'd trust him, but I know he's lying. I just don't know what it's about."

"But it sounded like you were saying all the things that happened were in the past. Is he still behaving strangely?"

"Well, not so much. He doesn't stay late. Tonight he left early because I asked to meet here and talk. But - but maybe it's some woman he met that time he attended a conference in Florida. I took the kids down to meet him when it had finished and we had a nice time, but I felt there was - I dunno, something not right."

She looked sad. And then her drink arrived and she took a large sip.

"Look, Jenny, all I can say is it may be nothing. Is it possible that it's a problem at work, or some kinda money issue he doesn't want to share with you?"

"I don't think so. I mean, I have access to all our finances, and we're doing pretty well. Just last week he came home all excited about a big new order that's come in, so I don't think the business is in trouble. I just feel it has to be a woman."

While she'd been talking, I'd been picking at my salad. She quickly finished her Margarita and ordered another. I decided to try to steer the conversation somewhere more cheerful.

"You say you went to Florida. Did you enjoy it? I think I heard your husband say you had kids. Did you take them with you?"

She talked about the trip as I finished my food and my Coke - and she downed another Margarita. She still seemed convinced her husband was having an affair but, I was pleased to hear, she'd seen no actual evidence. I found myself liking her, and I felt a bit of an asshole, knowing all the while that I was the one that had had an affair - even if it was only brief - with her husband.

I called the waitress to order another Coke. Jenny asked, "Don't you drink?"

"Well yes, I do. But not a lot."

"Are you driving home after this?"

"No. I was going to catch the bus or take an Uber."

"Then have a drink with me. I'm paying." She ordered two more Margaritas.

As we sipped our cocktails - me a little slower than her - she asked about my boyfriend troubles. "Oh yeah, Jake. Sorry, I've been trying not to think about him." I explained a little about our last night together but left out the part concerning the anal.

"I think you're right to stay away from him. He sounds like bad news," she said, finishing her drink. I'd drunk only around half of mine. She looked at her watch. "I supposed I'd better go," she said, with a sad expression. "Though I don't feel like going home. It's been really good talking with you, Tori."

"Well, if you'd like to carry on, we could always take an Uber back to mine and have coffee and talk some more."

She thought for a moment. "That sounds like a lovely idea, Tori. But I'm not sure about coffee. Would you mind if we went to the liquor store across the street and bought a couple of things? If you call the Uber, I'll only be a minute."

Back at my apartment, which she admired - more, I guessed, out of politeness than anything else - she mixed us a whole jug of Margaritas. By the time I'd had two - in addition to the one I'd mostly drunk in the diner - I was feeling a little woozy.

And talking of 'mostly drunk', I could see that Jenny was more than halfway to being loaded.

"So what made this boyfriend of yours - Jake? - what made him hit you like that?" Her speech was a little slurred.

I felt sufficiently relaxed to spill the beans. "I offered to try anal sex with him. But he's kinda big, and it hurt; hurt a lot. So I made him stop. Then he got rough. When I complained, he - he hit me."

"Men are such assholes," she said. "And all they seem to want is to fuck ours."

I laughed, and she joined in.

"Do you - I mean, does your husband...? Sorry, that's - that's very personal. I shouldn't ask."

"Do I let him fuck my ass?" she said with a smile. "Yes, from time to time. Usually, I enjoy it. See, he's not too big. I don't mean he's small, but these days, if we prepare properly, it doesn't hurt. Sometimes - actually, a lot of times - I get off on it. Once or twice he's made me come that way."

"Wow. Only - only I've never done it before, and I thought Jake loved me and it would all be great. But - I dunno. Maybe we were going too fast, maybe I should've waited. But the idea of it kept popping into my brain, and it seemed so naughty, so thrilling. It's like a taboo. Like something you're not supposed to do, so you start to crave it. What - if you don't mind me asking - what does it, er, feel like?"

The expression on her face changed as she recalled the act. "Well, it's hard to describe. I mean, I guess it depends on the individual. I talked to an old friend about it once when Tony first started to suggest we should try it. I knew she was pretty adventurous, sexually. She never married, but always seemed to have boyfriends who bought her nice things. She told me the right way to go about it, and that it could feel better than normal - you, know - pussy sex if your head was in the right place."

"Your head?" I couldn't see what kinda position you'd have to be in for that to work.

She laughed. "I mean, you have to want to do it. Or, rather, to have it done to you. It's like you were saying. Look, I'm not very submissive, and I understand that girls who are, seem to enjoy having a man dominate them by doing it. But - see, if you're feeling, like you say, very naughty, even kinda slutty, the idea of having a guy stick his dick up your ass can totally blow your fuses. Well, that's kinda how it is for me."

"But, I mean, surely it must hurt?"

"Well, only if you haven't prepared."

"Doesn't that kinda take the edge off it? I mean, shouldn't it be spontaneous?"

She laughed. "Tori, spontaneous anal sex is a good way to get a sore ass; maybe even a prolapse. But the preparation is half the fun. Walking around with a butt-plug in - especially a vibrating one - can feel so thrilling. Have you ever gone out without panties?"

I smiled at the memory. "Sure."

"Well, imagine walking around the mall with no panties and a vibrating plug in your ass, anticipating going back to your man and having him take the plug out and slide his dick inside. The first time I did that, I had pussy juices running down my thighs. And then when it happens - when his cock goes through that tight ring and just kinda pulls back, there's this sensation that's hard to describe, but it's a bit like having a guy with a very long cock make contact with the top of your vagina, behind the cervix. Have you ever had that?"