A Night Of Firsts With My Mother In

A Night of Firsts with My Mother-In-Law

Thanks to kenjisato for all the help editing

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I check my watch, 5:55am. I look to my left, to see T sleeping peacefully. I slowly move the covers off me, all the while watching T for any signs of waking. I slowly lift my hips and slide my underwear down in the back. I look at T and slowly set my butt back down, then slowly push the front of my underwear down enough to release my hard cock. T doesn't move.

I look down and smile at my hard cock. Fuck, I love my cock. I flex my cock, then slowly reach for it so I don't wake T. Once my hand is around it, I slowly stroke up. I close my eyes as I anticipate the downstroke. I slide my hand down my shaft, imagining Elaine, my mother-in-law, slowly impaling herself on my rock-hard cock.

"Aaaahhhh." Fucking utter bliss.

That first stroke is always amazing. The feeling of my hand sliding down my shaft, over every ridge, my foreskin slowly peeling back, exposing my mushroom to the fresh air. The feeling is akin to...

--thump--

I'm pulled out of my thoughts by the sound.

"Fuck, finally," I think to myself.

Without realizing I am now stroking my cock pretty fast, I slow down so as to not wake T.

I hear her door open and close. She starts walking towards our room.

I purposely had left our door wide open, 'cause I knew she would come to close it. She is getting closer. I slowly stroke my cock. I close my eyes, but keep them open a sliver so I can see her in the mirror opposite the door. She reaches for the handle and grabs it. She turns her head as she starts to close the door, and freezes.

She watches, with her mouth open, me slowly stroking my seven-inch cock. She unconsciously licks her lips, looks at my face, then back down to my cock. I'm starting to feel my balls tingle.

"Mmmhhh," I groan, inwardly. I'm gonna cum soon. Just then, T moves. My mother-in-law snaps out of her trance and quickly exits the room and closes the door quietly. As the door closes, I blow my load. Cum erupts from my dick and lands on my stomach.

"Fuck, that was amazing," I groan, and roll away from T. Cum is still shooting out of my cock onto the bed. I hear Elaine go downstairs. My cock is still rock hard and I have to pee. I wipe myself off with the bedspread and roll out of bed. With my cock making a tent in my shorts, I grab some clothes and head to the bathroom.

+++

My mother-in-law, Elaine, has always turned my crank. I have been married to T for over thirty years. I have jerked off thinking of Elaine, a minimum of once a day since the day I met her. Elaine just turned seventy and is still looking good.

Elaine is around five feet tall and T is about five-foot-three. Elaine, if I have to guess, is about 140 pounds; T is now about the same. T is a 38DD; Elaine is a 38D. I know this 'cause I went through the laundry hamper. Bent over they both look good; they both have the same asses. I had come close to grabbing Elaine's ass a couple of times, but had then noticed it was Elaine just in time. I always wonder if Elaine likes to get pounded from behind.

We have always gotten along well. We have a lot of the same tastes.

T and I have always had a pretty good sex life, two or three times a week, except for the last three months or so. Menopause has kicked in and she is always too hot, or feels crappy. She is not overly adventurous, missionary or cowgirl, that's about all there is. We tried doggy, my favourite, once, but it hurt her so that was it. I tried going down on her, but she did not like it-- so never again. As for blowjobs, if you want to call it that, she would kiss and suck for thirty seconds and that is it. I'm fifty-seven and have never had a hand job, other than mine, or a blowjob to completion.

Lately, I have been thinking a lot about my mother-in-law and all the ways I want to fuck her-- I realize that it has become an unhealthy obsession. I haven't had sex in probably three months, and my cock wants to be somewhere warm. I've been doing a lot of reading on the Literotica.com site; trying to find ways to seduce my mother-in-law and have sex with her.

I've read a ton of stories, and I think I have finally figured out a way to achieve my goal.

We haven't been to the in-laws in a few months, so the last time Elaine called to chat, she asked if we could come to visit. Great, time to put my plan into action.

The first part of my plan is to expose myself to Elaine, so that when she looks at me afterwards, she will think about my cock.

She is always up first, so I have followed through on my plan to expose myself and have her watch me jerk my cock.

Which brings us back to now.

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I finish going to the bathroom, clean up and stroke my cock a few times, so I am semi-hard, going downstairs. I have decided not to wear any underwear, just my grey sweatpants. I open the door and I can see into the family room. I can see the couch and Elaine sitting there. All I can see is from her waist down. I reach into my sweatpants and stroke my cock. Now from experience, I know that from where she is sitting she can see my lower body, but not my face. As I start heading down the stairs, I emphasize every step to make sure my cock bounces.

I reach the bottom of the stairs, stop to stretch, and push my cock out; with my eyes barely open, I can see her looking at my cock. I finish stretching and walk into the family room. I look at Elaine and see her eyes move from my bulge to my face.

I smile. "Good morning! How was your sleep?"

"It was good," she says, smiling. "Yours?"

"Mine was great. I think I had an awesome dream, but I can never remember them when I wake up, but I feel great this morning." I could see her look down at my cock, so I flex it.

Blushing, she looks back at me. "D-Do you want coffee?"

"Sure," I say, with a smile.

Elaine stands up and starts walking to the kitchen. I notice she is not wearing a bra and her nipples are starting to show.

"I can get it myself," I say, and start to walk into the kitchen.

"No, no, that's fine. I will do it. You just sit and relax," she says. So I sit at the table in the kitchen and watch Elaine as she walks around in a T-shirt and a pair of sweatpants. I haven't seen her without a bra on before. It is nice to watch her tits move around freely.

"So, what's up for today?" I ask.

"I need to go to the mall to do a bit of shopping," she replies.

"I assume T is gonna go with you?" I ask.

"Yes," she says, as she places my coffee on the table.

"While you guys are there can you pick me up some beer, whiskey and whatever drink you guys want to have for the games tonight." I take a sip of my coffee and blatantly look at her tits over the rim of my cup.

"Okay, we have a few things here, but I can pick up beer and some other drinks."

I look up from her tits. She blushes.

"T likes the frozen slushy-type of drink, so if you get a couple of those, that will be way more than enough for her."

"Ha. Yeah, unfortunately, it doesn't take much for me nowadays, either," she says, with a smile.

"I'll keep that in mind." I smile and wink at her. "More coffee please," I say, as I hold up my cup.

Blushing, she hesitates and looks at me.

I'm not usually that assertive with her, but it is another part of my plan.

She brings over the coffee pot and starts to pour. I make a point of looking directly at her tits.

"Thanks," I say, and keep my eyes glued to her nipples and lick my lips.

"Mmmm, that smells wonderful," T says, as she comes in and sits down at the table.

Blushing, Elaine asks, "Do you want a cup?"

"No," I say. "Get her tea."

"Yes, tea. That would be lovely, thank you," T says, smiling.

"Morning babe, I hope you had a good sleep," I ask.

Elaine comes over with a cup, teabag and the kettle.

"Yes, it was great; yours?" she says, leaning over and kissing me.

Elaine slowly starts to pour water into the cup.

I see Elaine look at me. I stare at her tits, lick my lips and look up to her eyes. She is still looking at me and starts blushing; she quickly looks down to the kettle.

"I feel great, I know I had a great dream, but as usual, I can't remember what it was about."

They start talking about their plans for the day.

I sit there, and sip my coffee as I watch Elaine move about the kitchen, her tits swinging and jiggling as she moves. I slide my hand down and start rubbing my sweats-covered cock. I'm getting harder by the minute. Elaine stops, turns and bends at the hips to get something out of the bottom cupboard. I start rubbing faster. She stands and turns around; now, I'm looking at her crotch. I lick my lips and look up to her face. She is blushing and looking at me. She can see me rubbing myself.

T gets up and walks toward the sink.

I stand up and my semi-hard cock pitches a tent. Elaine's eyes roam down to it. I grab it through my sweatpants and rub it. T starts to talk, I'm not sure what she is saying, but I leave to go to the bathroom on the main floor. I close my eyes, pull out my cock, and start furiously stroking it, as I picture Elaine's ass bent over.

I get pulled out of my fantasy by a knock on the door, and someone mumbles.

I quickly spin around and sit on the toilet.

"What?" I ask.

The door opens so I cover myself.

"We are changing then leaving. Do you want anything?" she asks.

"Yeah, to fuck your mom!" I think to myself.

"I mentioned to your mom what to pick up."

"Okay, bye, see you later," she says through a now closed door.

With a now limp cock, I just stand, flush the toilet,and wash my hands. I head upstairs and grab my phone. I go to the den, lie down, and watch some TV while browsing my phone.

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I open my eyes and I see a pair of beautiful breasts clapping above my face. When the tits part, I see Elaine's face. Her eyes are closed as she bites her lower lip, moaning. It finally dawns on me, she is riding my cock for all it's worth. Fuck, she feels so good.

"Hun? Hello?" I hear T's voice.

"Huh? What?" I groan.

"Roland!" T says a little louder, and I feel like someone is shaking me. I open my eyes and T is standing over me. She looks pissed and is looking at my crotch.

"What are you doing? You have a fucking hard-on!" she says, in a hushed, firm voice. "Who are you thinking of?"

"What? I... I don't know! You know I don't remember any dreams," I say, sitting up to hide my erection.

"Sure, likely excuse, pull yourself together; you don't want mom seeing that," she chides me, pointing to the tent in my sweats. "We need help to bring everything in."

"Oh, but I do!" I yell in my head, as I stand up and rearrange my softening cock. I head outside to bring in a pile of groceries. I put all the alcohol away, then pull out and open a beer.

"A bit early for that, isn't it?" T asks.

"What? It is almost two! Besides, it is never too early for an ice-cold beer," I say, as I take a long draw and walk out of the room.

I smile when I'm out of the room. Time to start the plan-- get wasted. Well, pretend to get wasted. T is going to be pissed at me, but if I end up fucking Elaine, it will have been worth it, I will grovel at her feet for the next however-long-it-takes for her to get over it.

I spend the rest of the afternoon outside drinking and chatting with the father-in-law, while T and Elaine get all the snacks and order pizza for the games.

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I hear the doorbell, and I check my watch. "Well, sounds like supper is here and time for the first game."

The father-in-law gets up and heads inside. I stand, stretch, and follow him in.

As the ladies are setting out plates, etc. for supper, I start to get everyone their drinks. I know the father-in-law will only have a few more and he will be ready for bed. T will only have a couple of her slush drinks and will be done after that. Elaine will only have a couple of pina coladas. As for me, I'm walking around with a partial chubby, thinking about sliding my cock in and out of Elaine's warm, wet pussy. I am starting to feel good. The alcohol has helped get rid of the nerves about putting my plan to fuck Elaine into action.

I take everyone their drinks and come back to get mine. I grab two beers out of the fridge, open them, and pour them down the sink and fill them with water.

"Hun, you're missing the start of the game!" T yells.

"I'm coming right now," I say, as I walk out of the kitchen with a 'beer' in each hand.

T looks at me and raises an eyebrow. I blow her a kiss and give her a wink. Excess drinking has always been a bone of contention between us, but it is needed, at least the look of it, for tonight.

As the game progresses, I pretend to be getting drunk as I go back and forth to the kitchen to top up drinks and get myself a few more, as well.

"What are you doing?" T asks.

"Come on, I'm not going anywhere, we are just watching the games and having fun." Without giving her a chance to respond, I kiss her cheek, slip past her and return to my seat. She looks pissed and ignores me for the rest of the night. She finishes up her slushy drink while scowling at me.

The second game ends and the father-in-law stands, and stretches. "Well, that was awesome."

I stand and give a fake stumble, raise my beer, "Sure the fuck was," and pound it back. "Want another?" I ask the father-in-law.

"Ha, no I'm good. I'm off to bed. Go ahead, enjoy yourself." And he heads upstairs.

"I, I think I will, anyone wanna join me?" I turn and look at T and Elaine. If looks could kill, my head would be vaporized.

"No! And you can sleep down here tonight!" T spits out, and stomps up the stairs.

Fuck, tomorrow-- no, the next month-- is gonna be hell to pay.

As I turn to look at Elaine, I ask her, "Well, I guess it's just me and my favourite mother-in-law. How 'bout another?"

"Ha-ha-ha," she laughs. "I don't think so. I've had enough. It'll probably keep me up all night as it is, and I think you're in enough trouble, you should go to bed," she says, smiling at me.

"I'll get you a blanket and pillow." She stands. "I'll take that," and reaches for my beer.

"Ah," I say, as I pull my beer out of her reach, and stumble a bit. "No so fas," I slur, and down the remaining. "Here you go, my darling." I hand her the empty beer. "Tha-thank ya," I say.

Elaine smiles and turns to walk to the kitchen, as I head up to the bathroom to get ready for bed. I go to our room and the door is locked. I can hear T lightly snoring already.

"Perfect! Fuck, this is going well." I turn and head to the bathroom. I hear creaking and realize Elaine is coming up the stairs. As I brush my teeth, I start to stroke my cock. "Now, I just hope Elaine can't fall asleep and comes down for a drink."

My cock is now standing at attention, and I have to stuff it into my pants, and go downstairs to wait.

I open the door, and Elaine is standing at the top of the stairs.

"I put your blanket and pillow on the couch. Can you make it down okay or do you need help?"

"Ha, na, I'm gooood!" I say, with a goofy smile.

"Okay, well, goodnight," she says. I notice her eyes trace down to my crotch, as she goes into her room.

I slowly head downstairs to my makeshift bed Elaine has made up. I take my clothes off, leaving my underwear on, and turn the light in the living room off. I lie down, pull my cock out, and slowly stroke it as I wait.

As always, there is a small nightlight in the kitchen, just enough so you can see where you're going if you come down in the dark.

I look at my watch. "Almost time." I think to myself. Whenever we visit, I always get woken up by Elaine at around two in the morning as she goes downstairs for a glass of water. Hopefully, her drink has not knocked her out.

--creak--

My heart just about explodes. "Fuck! Show time!"

More noises from above. My cock is as hard as a rock. I throw the covers off me, with one leg off and one leg on the couch; pillow on the floor; arm above my head and one hanging in the air. My cock is pitching a massive tent. My goal is for her to come closer and cover me up.

I hear a door open and close. I can tell it is Elaine from the light footsteps coming down the stairs. I turn my head to the left and I watch through slitted eyes.

She stops at the bottom of the stairs, and looks my way. With the dim light, she can see me. There is no way she can't see the tent in my shorts. She starts to the kitchen.

"Damn," I curse to myself.

She stops, looks again, turns and comes down to the living room.

"Yes!" I scream in my head.

She slowly moves over towards me. I can tell she has no bra on, as her tits freely move side to side. The tee is short, coming down to the top of her thighs, low enough so as to not show her pussy. She moves to my feet. Gently, she lifts my leg and sets it on the couch, all the while looking at the tent in my underwear.

She just stares at it for a few seconds. I make my cock twitch, and it snaps her out of it. She looks at my face and then back down to my cock. She bites her lower lip and pauses for a couple of seconds. Gently, she reaches down for my hand. She places her right hand under my elbow and lifts and places my arm beside me. My cock twitches. She freezes. I move my legs. She looks at my face to see if I'm waking up. Satisfied, she turns, and bends to pick up the blanket.

I can see her panty-covered ass. "Fuck, I just wanna reach out and grab it." My mind is in overdrive, and my cock is throbbing.

I slide my hand down my shorts, grab my cock and start to slowly stroke it. "Mmm, T, so gooo..." I quietly mumble.

Elaine freezes and waits, holding the blanket above my legs. She slowly lowers it and looks at my face. Seeing my eyes closed, she continues to cover me then stops. She doesn't move; she just watches for what seems like an eternity, but in reality, it was only thirty seconds, and gently covers me up, watching me stroking my cock under the blanket.

She smiles, turns, and walks to the kitchen to get a glass of water. I quickly and quietly get up and walk to the kitchen.

"Mmm, T, you look so good in my tee," I quietly moan, as I move in behind her, forcing my hard cock into her ass, as I wrap my arms around her and grab her tits.

She spits her mouthful of water out and drops her cup. Thankfully, it is a plastic one.

I grind my cock into her ass and kiss her neck, while taking a deep breath-- man, she smells amazing.

"Mmm, you smell good enough to eat," I whisper, as I massage her tits.

She is trying to wrestle my hands from her tits with no luck.

"Roland!" Elaine spits out. "You're drunk. It's me, Elaine! Let me go."

She continues to struggle, and as she does, my cock is being stroked by her ass.

"Nice try," I whisper, and pinch her nipples which have started to push into the palms of my hands.

"You've been teasing me all day; leading me on for weeks now, always telling me later. Always later." I pinch her nipples harder.

"Ahh, st-stop," she groans, as she continues to squirm.

"Your nipples are feeling wonderful tonight. A lot harder than usual. I like it," I whisper in her ear.

"Oh, oh god, stop!" she whispers.

"We haven't fucked in over three months." I grind into her some more and release one of her tits and slide my hand down her side to her hip under the shirt and to the warmth between her legs.

It takes her a few seconds to realize what I am doing, and she starts clawing at my hand and forcing her legs together and ass out. As I rub her soaking, panty-covered pussy, she pushes her ass back, into my cock, to get away from my hand.

"See, you know you want it, you're soaking wet, you slut. My cock is so hard and wants to explode in that wonderful pussy of yours." I lean down and gently kiss her neck.

"Ah, of god. Please stop. Roland," she begs.

I pull my hand from between her legs, and slide it up under her shirt and grab her bare tit, squeeze it, and trap her nipple between my fingers and squeeze.