Escort Neighbour Pt. 02

I meant the original Escort Neighbour story to be a "one of". It didn't matter to me what happened next. I would rather the reader be free to imagine many happy endings; however, I've had many people ask me for more and so I thought, why not? What happens next? How would a married man deal with a rich escort neighbour? Where would their relationship go? Could they have a future that was sustainable and realistic? So here is Part Two. Please enjoy the continuing story or Bill and Jennifer. You need to read Part One, first.

Oh, one last thing: if you don't like ass-play then don't read this and rate me one star like some other reader did with another one of my stories. Move on.

*****

That night, after having sex with Jennifer in my fort in the backyard, I had dinner with my wife Nancy. I had made my homemade ravioli, filled with crab, and covered with a lovely Béarnaise sauce. Sadly, we had a cheap twenty dollar Pinot Grigio to wash it down. But it was a lovely meal coupled with a fresh salad.

In the middle of dinner, I found myself shaking and excused myself and went to the bathroom. Guilt wracked me like no other time when I had cheated on my wife. It surprised me with the intensity and I spent time just staring at my face in the mirror looking for signs of the guilt that was consuming me. My normal face stared back, but I was certain my eyes were a little wider than normal.

Jennifer had gone home soon after we had fooled around. I had gone inside extremely satisfied and showered. I had a glass of scotch and went outside to have a smoke. I had looked up at Jennifer's window and found her smiling down at me, chest bared, and her gorgeous breasts pressed up against the window glass. I had smiled and waved and felt warmth course through me while staring at her beautiful, tooth-filled smile. She waved and disappeared inside and then the guilt hit me again.

I shrugged it off and sat confused sipping my scotch. The only time I had ever felt guilt like this was after the first time I had cheated on my wife with a service provider in New Zealand. This time it was different. It was far more intense and weakened me physically.

Now in my bathroom looking at myself I tried to find a way past it. I didn't understand why it was happening. Thoughts of Jennifer kept flooding my mind. I could see her again, lying back with her legs spread and holding her pussy lips open for me to see all of her. She was so hot and so beautiful. My cock surged in my pants. I remembered the first feel of her breasts in my hands. So soft, so warm, and with her nipples so responsive and hard against my palms.

I remembered how wet she was. It had been so long since I had felt a woman so wet for me. To have that effect on a woman is empowering. And I remembered her taste. So sweet, so fragrant. My mouth watered and I needed to taste her again. I needed to plunge my cock back inside her and see her eyes light up in joy. I needed to see those green, green eyes boring into mine from a gorgeous face framed in luxurious red hair.

My cock hurt with strain. I pulled it out and stroked it furiously thinking of Jennifer. I jerked myself for only a minute before my cum surged out and splashed onto the bathroom counter. I sucked in gulps of air and squeezed the last drops of my cum free. I looked into the mirror and saw my cheeks flushed red. What the fuck is wrong with me? I questioned myself. I never cum that fast.

I could only cum once a day these days. Age has a way of slowly a man down. Sexual desire was always there hovering, but my ability to pleasure myself had dwindled. And now today I've cum three times. She has such an effect on me.

But why the guilt? What the fuck is up with that?

I calmed down and cleaned up using a wet wipe on my cock. I washed my hands and headed back to the dinner table. Nancy looked up briefly and then returned to reading an eBook on her iPad. I sat and we finished our meal in silence. When we were done, I said I would clean up and Nancy kissed my cheek and said she was heading to bed.

She always went to bed early. I would go to bed around midnight to find her snoring loudly. I would lay on my back and fatigue took me and I would roll over onto my stomach and think dirty thoughts about women until sleep would take me. Nancy always tossed and turned all night and she would rise early and be gone for work before I staggered out of bed. Usually exhausted.

She had gone to a sleep lab once. They diagnosed her with sleep apnoea. She now had a CPAP but rarely used it. Continued exhaustion had sent me to the same sleep lab. I still remember the specialist talking to me the next morning.

"The problem, sir, isn't you. Your problem is your wife."

Nancy didn't find it funny. I did, because the sentence had so many meanings to me.

I should mention I travel sometimes for book interviews. When I am away from Nancy, my sleep is fantastic. I can get better rest with less sleep in a hotel room than I can lying next to my wife. That's my life and I'm used to it. Kind of. It sucks having no sleep and no sex. It's frustrating.

The truth is: my frustrations with my life pours out of me into my books. The erotic novels are raw and emotional and filled with depraved sex. It's what I need and want. I've imagined all sorts of sex and some of it surprises me. For example, for a while, I was certain I was bi-sexual. I had a long period of craving cock that surprised me greatly. Then I realised I didn't crave cock so much as the liberty of having crazy sex and there being a guy there. My lust is so great that it just factored in. Porn probably is much to blame. I watch cocks plunge into holes and spew cum all the time. The good news is when I'm not pleasuring myself, and when I force myself to think of sex with a man, I feel quite repulsed. But, when in the throes of wild imagined sex with women - usually more than one at a time - throwing a cock into the mix doesn't faze me at all. Strange, isn't it?

I'm not sure what it means, but I've never had to worry about it. I will never have the opportunity to test myself and my limits. Life rumbles along and my porn, my writing, and the occasional tryst with a service provider (SP) or massage attendant (MA) keeps me happy and sane.

Nancy disappeared upstairs and I cleaned up supper and went outside for a smoke standing beside the fence. In a moment, I heard Jennifer's patio door open and saw her come out in a silk bathrobe and saunter over to the fence on her side. The robe hugged her figure and her nipples pressed against the material. My cock twitched and I felt a sexual hunger rise within me. She lit a smoke and smiled at me blowing her smoke past those sensuous lips of hers. My guilt fled and I felt at peace at once. I found myself smiling back and wanting to hug her hard.

"Hey, sexy," she said. I could hear a hunger in her voice. "How's your night?"

"Hey, you," I replied. "Pretty good. Been thinking about you all night."

Jennifer smiled wider. "God, me too. I just finished banging my pussy with my favourite vibrator thinking and wishing it was your cock."

I blinked at her. Even in my erotic novels I never had the women speak like that. I didn't know how to respond.

"What? I masturbate all the time, Bill."

"You do?"

Jennifer took a drag and eyed me. "Yeah. You don't think women masturbate?"

"No, not really. Not like men do."

Jennifer chuckled. "That's probably true. Well, I do. I spend so much time pleasuring men and rarely do they pleasure me. It gets frustrating, you know? Imagine yourself fingering and eating gorgeous women all day and never having your cock touched or sucked or fucked. It would drive you to masturbate. I usually end my days stuffing a vibrator in my pussy for release. It helps."

"I never really thought about it."

"Worse is when the client demands to get you off. All men need that. They need to bring a woman to orgasm. I think it comes from a man's own desires and experiences. Men need to cum. To release. They think women need that as well. They're not wrong but a woman can cum multiple times. It's rare a man can get me to cum in the right way."

That sounded horrible to me and said so.

"It depends on the guy. The right guy can get me off in a heartbeat." She blew out smoke and gazed at me as if waiting for something.

I thought over what she had said. It sounded so very sad to me. For a man sex can just be physical. It is about the release. To ejaculate. But the best sex is with a willing partner. Getting each other off. It's physical, but a large part is emotional. The best sex is with someone you love. It's a validation. Proof. I took a drag and Jennifer snorted.

"What?" I asked her.

"I was waiting for you to say something. To ask me how it was for me."

I raised an eyebrow. "You mean with us? Today? You loved it."

Jennifer's eyes opened wide and she coughed out smoke. "Wow. So sure of yourself!"

I frowned at her. "You did. Just as much as I did."

Jennifer eyed me for a moment and then nodded, "Yeah, I did. I truly did. That was the best sex I've had in a very, very long time, Bill. I'm not just saying that."

I nodded. "Me too. Thanks."

"I want you to fuck me right now, Bill."

I laughed. "Nope. Not gonna happen."

Jennifer looked hurt. "Please?"

"I'm sorry. I can't. Nancy is right up there," I pointed at the second story of my house for emphasis. "And honestly. I just jerked off and I'm spent. I'm not young like you."

Jennifer looked surprised. "You came twice with me."

"Yeah, and now a third time in my bathroom. That's a lot for me."

Jennifer nodded. "I feel sorry for men, being limited that way. So, in the bathroom: were you thinking of me?"

I nodded and butted out my cigarette. "Fuck yeah."

"Good. Now kiss me goodnight."

I leaned over the fence and Jennifer kissed me long and deep. Her tongue darted into my mouth with hunger. She danced her tongue over mine and over my teeth. She sucked my tongue into her mouth and I moaned. She broke the kiss but kept her mouth close to mine and stared into my eyes. "I bet I could make you cum a fourth time..."

I kissed her quickly. "I think so, too, but I need to regenerate."

"Mmm," she murmured. "More lip-gloss for me. Okay, I'll wait. You rocked my world, Bill. I'm so glad you're my neighbour."

"Me too," I licked her lips and she purred. "So what happens next?"

"Between us?"

I nodded with a tiny motion of my head.

"One day at a time. I have a full day tomorrow. Can I see you after?"

My mind reeled. A large part of me had managed to ignore the fact that my neighboured fucked men for money. She wasn't mine, not really. She was a sexual being and I was only one of many. I didn't know how to process it.

I hadn't answered her and she pulled her head back a little and looked into my eyes. "You okay? You know what I do, Bill."

I nodded and kissed her. "I do. It's just a little much to process right now. Give me time."

Jennifer bit her lower lip. It was such a cliché move, but it looked so natural and so cute. I felt my emotions rise within me. She was so beautiful. "Okay. We'll talk tomorrow. Okay?"

"You bet."

Jennifer smiled and kissed me and then pulled back from the fence and took a few steps backwards. She opened her kimono wide and revealed her gorgeous body to me. Her nipples were hard and rising up from her breasts. I could see the lips of her pussy and my mouth watered.

"My pussy is so fucking wet for you Bill. Think on that lying in bed tonight, mister." She winked, snapped her robe shut and sauntered into her house, closing her patio door behind her.

* * *

The truth was I was so exhausted I passed out when my head hit my pillow. In the morning, I woke later than normal and staggered downstairs for a coffee before heading outside for a smoke. It was just before ten and the day was gorgeous. I heard a car drive past outside and in moments I heard Jennifer's front door open and close. I looked up at her bedroom window but the drapes were closed.

I felt a twinge of jealousy and squashed it.

After a time, I went inside and showered. I made a fresh cup of coffee with my Keurig, went outside and lounged in my fort. My laptop lay closed and I had no interest in writing today. I ended up smoking too much and drinking too much coffee waiting for something. I didn't know what I was waiting for. I imagined what Jennifer was doing and wished it was me with her.

Close to noon I heard Jennifer's front door open and close and a moment later a black BMW sped off down the street past my house. I waited and thirty minutes later Jennifer came through my house and out onto my deck. She had walked through my house like it was hers and I felt good about it. I liked her coming and going from my house like it was hers. I could get used to it.

She was freshly showered, her hair wet, and she was wearing simple track clothes. She sat down next to me and stole a cigarette from my pack and lit up. She blew out and watched me. She looked sexy in anything she wore; I looked away and sipped my coffee.

"Out with it," she said.

"Out with what?"

"You know. Just say it. Rip the band aid off."

I glared at her.

"Want to know what he did?"

I said nothing.

She placed a hand on my thigh and rubbed it. "He's one of my favourites, Bill. He tries to please me and usually does. Today he tongued my asshole like a starved man. I really like that. I mean his tongue was right inside my asshole. When he thumbed my clit, I came. Honestly, I wished it was you, but it wasn't, obviously. We know each other pretty well. I know what makes him tick. He gets me off right away and then it's all about him.

"We don't talk much. Just two hours of sex. His thing is being ass fucked with a large strap-on. It's pretty hot. I love fucking a man's ass. Especially when they hate it at first. He does. Hate it, I mean. It demeans him. Debases him. He needs that. Then he gets into it. I fuck him really hard, Bill. He likes being on his back when I do it. He strokes himself eventually. He has a large cock, but it's strangely red all over with a large swollen head. But a head so soft, like velvet. I love feeling it filling my throat. Jamming itself in, cutting off my air. But it's rare he lets me suck him off.

"I fuck his ass hard but he never comes from that. To make him cum, I berate him. Call him all sorts of names. Tell him he's useless. With a shitty small dick. It's not though. It's fucking huge. Thank God, he never fucks me with it. Then I squeeze his scrotum right about the balls. I squeeze hard and yank them down. He cums every time like that. A shitload. A massive load more than any other client I have. It's shocking. The first time he came I thought something was wrong." She took a drag of her cigarette and laughed a little.

She butted it out and made a tsk sound. "Then he cries and I hold him tight and rock him and tell him how wonderful he really is. He suckles me like a child. I clean him up and he heads back to his office. He runs a multimillion-dollar corporation. He's always strong and always in control. With me, he gets to be something else. Not in control. With no power. Men don't want what they already have, you see."

I was staring at the outdoor carpet on my deck tracing the patterns with my eyes. I didn't know what to say. I had never had a conversation like this before. I was angry at her and fascinated at the same time. I didn't want to hear the details, but I wanted to hear more.

"Look at me, Bill."

I did. Her eyes were a little red. She looked upset and I knew I was the cause.

"I fuck men for a living. You need to get past that."

I nodded.

"I have another client in a couple of hours. I need to get ready for her. She wears me out and I need to prep myself. She likes me clean as a whistle inside. She has this thing for fucking my ass with a dildo and then sucking it off. She makes me suck it, too. And fuck her ass. Fucking hot sex, actually. I adore women."

I stared at her. My cock was hard, I realised. It had been the whole time she had been describing her sex with her first client. Hearing her having sex with a woman stirred something male within me. Jennifer noticed.

"Want me to suck you off, Bill?"

I shook my head and frowned. I didn't know what she was doing. But she was making me angry. She was pushing me.

"Okay. Talk to you later."

Jennifer rose and disappeared into my house.

A little while later I realised that my anger had replaced my jealousy.

* * *

Around one in the afternoon I watched a small woman drive past in a Cadillac SUV. I saw her come up the walkway and marvelled at her tiny body and her lack of tits. She disappeared into Jennifer's house and a little while later I heard a shrill voice cry out in pleasure with the word 'Yes!'. To have heard it so clearly in my backyard it had to have been very loud inside.

My cock grew stiff and I imagined Jennifer getting pleasured by the small woman. I grabbed my cock through my pants and squeezed it. I looked up and noticed Jennifer's bedroom window was open a crack. I knew at once it was intentional. Jennifer was punishing me.

For being an asshole, I realised.

I sat in my fort and listened to the little woman being pleasured. She was shrill and loud and I heard foul language that had my ears burning. I opened my laptop and copied a few choice phrases for future use.

My cock hurt. I was so completely horny and wanted nothing more than to run upstairs to Jennifer's bedroom, burst in, and fuck anything in there. I smoked and waited. After an hour, the woman left. Soon after my patio door opened, startling me. Standing there was Jennifer. She looked flushed. She came over and stood over me looking down.

"Take it out," she ordered.

I undid my belt and pulled my jeans and then my underwear down and sat on the sectional. My cock was standing almost straight up. Jennifer shrugged off her sweatpants. Her pussy glistened with lube and I smelled cherries.

She wasted no time. She pulled off her t-shirt, straddled me and then moved up on my lap. She fumbled for my cock and found it and then dropped herself onto me. I plunged deep inside her and knew at once it was not her pussy. I gasped.

"Fuck my ass, Bill," she moaned and started driving me in and out of her ass.

I lasted a minute. I ejaculated cum into her rectum with a hard grunt, relishing the sweet release. Jennifer came, too, crying out. Her anus squeezed me hard. She lay on me and I felt her sobbing. I held her and my cock spasmed inside her. The last time I had fucked a woman in the ass was easily over six years ago. It had never been like this. So raw, so amazing.

I didn't know why she was crying and I held her rubbing her back and ass cheeks. Eventually she stirred and pushed her hands on my chest to lean back. She looked down at me with red-rimmed eyes. She sniffed and kissed me gently. I was still hard inside her and loved the feeling of being so deeply inside her. Especially in her ass. I felt like I had been granted a special pass. I could feel her pussy hot and wet on my pelvis bone. Being in her ass lined us up differently and I liked the change.

"Why were you crying?" I asked her.

"It was just so wonderful," she smiled. "Seriously. I need this, Bill. You're what's missing in my life."

"What's that?"

She glowered at me and then squeezed her anus around my cock. "This. Intimacy."

Her response resonated within me. I needed this as well. Suddenly my guilt came flooding back. Jennifer noticed my expression.

"What is it?"

"I'm feeling guilty," I murmured. "I don't know why."

She smiled. "Because you need this, too, Bill."