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Helping Jan

Sometimes all you need is a little encouragement
The Last Time
We’d just finished having lunch together, a local café in her neighborhood, Friday afternoon. We used to work together several years ago; now we just got together once in a while to catch up. The day was warm for mid-October, and clear, with that wonderful golden light. I was parked around the corner. She lived only a couple blocks away. I used to live in this neighborhood at one time, back when we both worked at the same company, and sometimes we would carpool, so I knew where her house was. We were standing on the sidewalk.

“Soooo,” she said, kind of looking around. She was always awkward about it, after we’d met up. She’d never say what was on her mind, just laugh nervously a lot. Laugh and kind of look around, look at me, look around some more. Sometimes I wouldn’t do anything until she said what was on her mind, even though I knew what was on her mind. I’d make her say it, say the words. Other times I’d just ignore it.

“Let me give you a lift home,” I said.

That laughing again. Of course I was being facetious. By the time we walked to my car, she’d be halfway there.

“Come on,” I said. “My car’s down this way.”

I drove the block and a half and pulled up to the curb in front of her house.

“Well,” I said. “Thanks for meeting me for lunch. Sorry it’s taken so long for us to manage to do this again.”

“Sooo,” again with that, the finally, “Do you want to come in for a minute, see my house? You’ve never been in it. Or do you have to get back?”

“You’ve never invited me,” I said. “I mean, sure. I can come in for a minute. You can show me your remodeled kitchen; I’ve only heard about it. I’ve got some stuff I have to finish this afternoon that I have to get back for, but I’ve got a little time.”

We walked around the downstairs, the living room, the back deck, and finally the kitchen and the work they’d had done. Then it was that awkward departure point again.

“Well,” I said. “Guess I need to get going. It was good to see you.” Gave her a hug and then, because she wanted me to, a kiss on the lips.

She made that nervous laugh, so I kissed her again and she kissed me back. I reach around and put my hand on her ass to pull her in. We stayed like that, at the entrance to her kitchen, kissing, her breath quickening, tasting like the beer she drank with her lunch.

“You really need to get going?” she said when we broke.

“In a bit,” I said. I always like to leave myself a bit of a window, as it were, with my more recreational female friends. Then I kissed her again.

“What are you thinking?” she said.

“A couple things,” I said, looking around a bit, at the clock, in the direction of the door.

“Derek’s out of town,” she said finally. “He had some time off and went to visit his family for the weekend.” I already kind of knew that, since she never would have invited me into her house if there was any chance of her husband coming home early from work.

“Well, that was one thing I was thinking,” I said, looking her in the eye now.

“What else?” she said, a little more of the nervous laughter.

I put my hand between her legs, in the crotch of her jeans, and pressed. She stopped laughing.

“About you,” I said, low and whispery. “On your knees. Looking up at me while I fuck your mouth. Watching your lips. Going up and down the shaft of my cock. Watching you lick it. Suck it. Until I shoot a thick load… of warm cum… down your throat.” Still pressing the heel of my hand against her mound. “Or on your face.”

“Let’s go upstairs,” she said.

She led me to her bedroom, a messy affair of mismatched furniture and scattered clothing, an unmade king-sized bed that was too large for the space, a lot of clutter and dust. A couple of former academics and midway through their forties, and she and her husband still lived like college students, I thought. But it didn’t matter. I wasn’t going to be navigating this place nor spending much time in it. I took off my jacket and lay it on a chair next to the vanity. She was standing, backed up against the side of the bed.

“This is freaking me out a little,” she said. “Being in my own –”

“Take your jeans off,” I said.

She pulled down her jeans and kicked them aside. I put my hands on her shoulders and pushed her to her knees, unbuckled my belt and lowered my trousers and shorts. She liked this; she liked to be pushed to her knees or told to kneel down. My cock was half hard and I stroked it slowly in front of her face.

“I want you to suck my cock,” I said.

“Okay,” she murmured, glancing up at me and then back at my dick. Her hair was brown and cut in a bob, and I ran my fingers through it before gently clutching a handful of it at the back and pulling her forward, feeding her my hardening cock with the other hand.

She took the head between her lips and began to softly suck. I let go of it and she wrapped her own fingers around it. She began moving her mouth and tongue back and forth the length of the shaft. She sucked me at her own pace for several minutes.

“Put your hands on my hips,” I said. “I’m going to fuck your mouth.”

I put my own hands on either side of her head and slowly began to fuck her mouth. She made a muted little grunt at each thrust. When I was getting close to coming, I pulled my cock from her and told her to lie back on the bed. I pulled down her underpants, then put my hands under the crooks of her knees and spread her legs apart. She wasn’t big on tidiness in other respects either, and the ample thatch of pubic hair glistened with her wetness.

I knelt down between her legs and smoothed my fingers over her lips, spreading some of the moisture around before bringing the tip of my tongue to her slit and working it in. I licked up with some pressure, flattening my tongue hard against her clit and then flicking it with the tip. I lapped at her cunt, getting a rhythm going, and then slid two fingers inside her. I alternated tonguing her with some light sucking of her clit. She had her arms outstretched and was clutching and kneading fistfuls of sheet.

She usually came fairly quickly and without much effort, but I could tell she was having trouble this time. Maybe it was the unusual circumstance of being in her own bedroom. After a bit, I added a third finger, stretching her pussy, and began fucking her more rapidly. I left off licking her clit and began frigging it with the thumb of my other hand. I could feel her body seem to quake and then stiffen, quake and then stiffen, approaching that crest, and as she finally started to come, I brought my tongue back in contact with her clit and licked it rapidly while she grunted and bucked against me.

While she was still stretched out on the bed with her eyes closed, panting lightly, I stood up and slid my stiff cock inside her. I had never fucked her before, didn’t really know if she wanted me to, but I didn’t ask. Her pussy was sopping. She seemed almost oblivious to the fact that I was inside her, so I slammed myself hard into her and she grunted from the impact. I fucked her roughly like that for a minute or two before pulling out and telling her to get back to her knees.

She slithered down off the edge of the bed to the floor. Her forehead glistened with sweat. Her hair was disheveled, sticking up in the back. Her eyes were glazy and only half open. She looked like she was drunk.

“I want to finish you,” she said and reached for my cock, took it in her mouth and began bobbing along its length.

“That’s it,” I said. “Suck it. Suck my cock, baby. Suck it and make it come.”

I grabbed handfuls of her hair and set the pace, easing her mouth back and forth over my cockhead.

“I haven’t come in over a week,” I said. “I hope you can handle it.”

“I want it,” she said between sucks.

“Fuck it with your mouth,” I said through my teeth. “Fuck that cock with your mouth like you want that cum.”

Her eyes had been closed all the while but when I said that, she opened them and looked up at me, looked up at me as I pumped my cock between her lips. If it wasn’t a genuine pleading look, it was a good bit of faking and that was enough for me. My legs were trembling.

“Yeah,” I grunted. “You’re gonna make me come. Fuck.”

I came in her mouth. She held the head of my cock between her lips as it pulsed several shots of warm semen over her tongue, and I grunted and coarsely told her to swallow it, get it all, that’s it, swallow that fucking jizz that you’ve been waiting for.

“Mmm-hmm, mmm-hmmm,” she kept repeating

When I was finished, I pulled my spent prick from her mouth.

“Fuck me,” she whispered and shuddered a little, wiping her lips with the back of her hand. “That was a big fucking load.”

***

The Time Before That

Our original plan was to have a drink for Happy Hour at a place that was on her way home from work and not far from where I lived. But when I met her out front, I changed my mind and told her to come with me.

“I have good liquor at my house,” I said as we pulled away from the curb.

“Is your… are you…” she was stammering a little, once again, not getting the words out.

“Yeah,” I said. “I’m in bachelor mode for a couple days.”

We’d had a couple glasses of scotch, and then I took her upstairs to my bedroom and told her to kneel down. She was still in her work clothes, jacket and skirt and blouse.

“I wanna suck you,” she said. I knew that she was at least a little drunk, but she might have been more than I realized.

“I know,” I said, taking down my pants and stepping towards her. “Just stroke it a little first.”

She took my cock in an underhand grip and gently pulled on it. She slipped her other hand down the front of her slacks and started rubbing herself.

“I want it,” she murmured. Her eyes were closed and she had a dreamy look on her face. “I want… cum.”

She opened her lips, took my cock between them, and began to suck it softly. She played the tip of her tongue over the cut of the head, making soft little slurping sounds that, quite honestly, heightened the excitement for me. Then she began to move her lips more firmly over the head and the shaft, picking up the pace.

“Oh, yeah,” I whispered. “That’s so good. I think we’re going to have to have you suck my cock much more frequently. This needs to be a regular thing for you.”

“Really,” she said, her eyes still closed, continuing to suck me.

“Yeah, I think you need at least two or three loads of my cum a week.”

“Mmmm-hmmmm,”

I liked the idea of a cum slut who’d be happy to service me on demand, but I honestly didn’t think Jan would be the one to fill that role. Talking about it turned me on, though, and Jan—or, slightly buzzed Jan—seemed to be enjoying the notion as well. She was making little mewling sounds of pleasure as she worked her lips and tongue over my cock. I needed to get a little whiskey in her more often, I thought. It seemed to whet her appetite for the cum chaser I was about to give her.

I grabbed her by the hair and pulled her head back slightly.

“Open your mouth, baby,” I said, taking my cock from between her lips and stroking it.

She looked up at me a bit sleepy-eyed and opened her mouth. I placed the head of my cock against lower lip and began ejaculating, pumping out a generous load that covered her tongue with a thick, milky coat, grunting with each throbbing shot.

“Mmm, very nice,” I said. “Swallow that, baby.”

***

And The Time Before That

We were sitting in the front seat of my car, in an underground parking garage in the city, very near where she worked and I’d just bought her lunch. She had a good grip on the parking brake lever between our seats. Her pants were undone, and I had two fingers inside her pussy, which was extremely wet. Her eyes were closed. She was panting lightly. I finger fucked her as best I could. It was late spring and warm in the car.

I slipped my other hand into her pants and began stroking her clit with the tip of my middle finger. It was awkward, but I wanted to jack her off there in the car and still be able to keep an eye on what was going on around us and keep her as clothed as possible in case we had to suddenly stop what we’re doing.

Her cunt was soaked. I could have easily added a third finger if we’d been in slightly more accommodating positions. I continued pumping my fingers in and out while rubbing her clit. Then I leaned in closer and whispered in her ear:

“You’re such a dirty little slut, letting someone finger fuck you in the middle of the workday,” I said. “You like getting your wet pussy filled? You like feeling my fingers pumping in and out of your dripping cunt?”

She let out this shuddering groan, kind of a descending staccato, and thrust her hips forward, coming there in the front seat of the car. I slowed down what I was doing with my fingers but didn’t entirely stop, wanting to make sure she felt every bit of it until that post-orgasm sensitivity kicked in. She had two more small spasms.

I carefully extricated my hands from her pants. The inside of the car felt sweltering. I gave her my handkerchief and she blotted her throat and the back of her neck. I lowered the parking brake lever between us, then lifted my ass off my seat and began unbuckling my belt and unbuttoning my pants.

“When I get back to my office, I’m probably going to look like I just had sex,” she said.

“Just smile a lot,” I said. “Try to look mischievous, not sheepish. And stop in the ladies room first to freshen up a bit.” Did I really have to tell her that?

“My pants are all wet,” she said. “I mean, the crotch. There’s a big wet spot.”

“I’m not surprised.”

“Sooo…” she looked at me and quickly looked away, out the windows, around the lot. It was mostly full, with cars on either side and in front of mine. “Do you have time for me to… reciprocate?”

“Not when you put it like that,” I said.

“What do you mean?”

“Just imagine me moaning, ‘reciprocate… yeah, that’s it, reciprocate’ while your head is bobbing in my lap.”

“What should I say?” she said.

“You need to say, "I want to suck your hard cock until you shoot your hot cum in my slutty mouth and I can swallow your load." 

She said it, but with that nervous little laugh of hers.

“You’re going to have to do better than that.” I said.

She tried again; it really wasn’t any different from the first time, only louder. She was reciting. I shook my head slowly at her, then pulled down the elastic of my shorts and took out my cock. She looked at it.

“Again.”

She did much better. I took a handful of hair at the back of her head and slowly pulled her head down to my lap. She took my cock in her mouth and began to bob up and down on it.

Maybe it was the awkwardness of the car and the limited space. Maybe she was just in a hurry, or just overeager, but I wasn’t feeling it. Mostly she was just rapidly mouthing it, not really sucking or applying enough pressure.

“Let me help you,” I said. I pulled my shorts down a little further. “Lick my balls for a bit. Suck them.”

She started licking and sucking at my nuts while I jacked my cock. I would have preferred to be sucked off. To feel that inimitable sensation of a climax building from the work of an ardent mouth. But things rarely go the way you imagine them going when you’re back in your room jerking off. Whatever. She was still going to take a mouthful of my hot cum here in this parking lot, and the thought of that got me quickly to the brink.

She flicked the tip of her tongue quickly against my balls while I jerked my cock, the back of my hand brushing against her cheek. When I was just about there, I bent it down to her mouth and told her to suck.

“I’m gonna shoot,” I said. “Get ready.”

This time she actually sucked, taking my head between her lips and pulsing it gently while I spunked in her mouth, what felt like four or five good strong spurts of cream, though I had no idea how much there really was because she swallowed all of it.

***

The First Time

She was backed up against the desk in my office. Her pants were open, and I had one hand inside her underpants, running my middle finger up and down her clit, occasionally slipping it up into her very wet cunt. My other hand had a firm grip on her ass because she seemed unsteady. Her eyes were closed.

“I shouldn’t be doing this,” she murmured.

“You’re not doing anything,” I said. “Do you masturbate?”

“Yeah,” she breathed.

“Do you think about situations that don’t involve your husband when you do?” I asked.

“Yeah,” she made that nervous little laugh of hers.

“Do you feel bad when you’re done? After you’ve made yourself come?”

“No,” she said.

“Well this is no different,” I said quietly. “This is just like when you jack yourself off. You’re just getting a little bit of help.”

“Uhh. Uhhh,” her hands gripped the edge of the desk and she was bending back over it, and her breathing was promisingly erratic.

“Do you think about other men fucking you?” I said. “Handsome strangers, or guys that you know? Probably several guys, right? Taking turns? They bend you over a desk just like this one and fuck you hard from behind. The first guys fucks you and fucks you until he comes inside this wet pussy of yours. Then another guy takes his place, slides his big hard cock into your cunt and fucks it. They make you come over and over again. Is that what you think about? Then they turn you over and hold you down while they fuck you all over again, shoot their cum up inside you? One big hard cock after another, making your pussy come and come?”

She started coming, quaking under my grip. I pressed the flat of my finger hard against her clit and held her ass tight to keep her from toppling over or sliding down and cracking the back of her head off the edge of the desk.

I removed by hand from between her legs and tasted her juice on my fingers—more for her benefit, but I don’t think she noticed. She was dazed: in a kind of post-orgasmic fug. Talking to her and jacking her through that orgasm had gotten me pretty excited. I thought about getting my cock out, pulling her pants down, turning her over the desk and just fucking her. But she was out of it—limp, a ragdoll—and it just struck me then that it might feel too much like fucking someone who was passed out drunk.

“Why don’t you sit down?” I said, trying to ease her away from the desk and toward my reading chair. This roused her slightly and she stood up on her own, looked at me kind of foggily, half-smiling, and then pushed her slacks and underpants down around her ankles.

“I don’t know,” I said. “Remember, you said you shouldn’t be doing this.”

She shrugged, though I didn’t know if it was a “whatever” shrug or a “too late for that now” shrug.

“Maybe I can…” a little laugh, looking back and forth at me and, I don’t know, something else in the room that wasn’t me.

“Maybe you can what?” I said.

“Maybe I can… pleasure you… orally?”

“Maybe,” I said. I stepped toward her and she dropped to her knees. “Do you eat cum, Jan?”

“Sure,” she murmured not at all convincingly, and she was looking at down at the floor.

“Jan,” I said, more sharply so she looked at me. “Do you eat cum?

“I’ve thought about it a lot,” she said.

“Never had a guy come in your mouth?”

She shook her head. How could that be, I wondered, but this certainly wasn’t the time to ask, and I really didn’t want to know the particulars anyway. I unzipped my jeans and showed her my cock.

“I’ll bet those guys you think about when you’re masturbating do, huh? I’ll bet you imagine them fucking and fucking you and then finishing in your hot, hungry mouth?”

She slipped a hand down between her legs and started touching herself.

“Yes,” she said, so softly I could barely hear it. She was watching me slowly stroke my cock before her.

“Spurting in your mouth,” I whispered, leaning in. “All that hot cream… And you swallow it all down, don’t you?”

But she didn’t answer. She couldn't.

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Comments(3)


LASARDaddy
Posted 20 Feb 2014 12:03
Very unique and a great story. Good luck.
mitchawa
Posted 13 Feb 2014 18:32
I liked the three sex scenes, but I'm still looking for the seduction.
HotBttmInBriefs
Posted 13 Feb 2014 14:10
I really enjoyed that. It was a unique approach. Good job and good luck.
 

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