Checking in. [MF]

This story starts out a sad one. One of my friends, Nate, lived a little less than a quarter mile from me back in high school. He moved to that house my sophomore year. We were friends before he moved there, but after that we became extremely close. We hung out almost every day playing Madden and drinking Mountain Dew. That friendship has lasted to this day. Nate is now in the Navy, so obviously I see him much less but still talk to him frequently.

But the reason (and I’m not sure this is exactly true but this is what I think) that Nate is even in the Navy is because there was some heart ache I think that he was running away from. In late 2018 Nate’s dad died of a heart attack. Now Nate’s dad kind of dug his own grave, as insensitive as that sounds. He drank a little too much, chewed tobacco, wasn’t super active and didn’t have the most heart healthy family history. But it’s not like that made it any easier for any of us. Grant was a great guy and everybody loved him. Grant and his wife, Kelly, had raised two kids to adulthood and had adopted a third girl who was ten when he passed. The whole situation was terrible, but they seem to be getting through it.

But now, for the part that doesn’t make me borderline nihilistic.

Before Nate left he asked me to just check in on his mom every once in awhile.

I met Kelly when I was 16 or 17, and let me assure you that there was no weird shit going on from a young age or anything like that. This woman was like a second mother to me. It was weird how well we got along though, and really the vibe was much more of a little brother/older sister vibe, even though she was, I think, forty or forty one when I met her. Me and my parents didn’t have the best relationship growing up and Kelly was one that kinda filled the hole of some parental voids. She would give me girl advice. One time when my parents and I had a hard falling out she told me to sleep in the basement for a few nights, even though I’m sure she knew deep down that I was most of the problem in the rifts that I had with them.

But after a few years passed and I got to being older, there would be blips of something else from that woman.

Now let me first stop and give a description of myself. I am now 25. I’ve been working out since my freshman year of high school football and one of my hobbies is fitness. I eat really well and enjoy working out, doing yoga and running. I have a great sense of confidence in myself because of it and do fairly well with girls because of my that. I have shorter blonde hair with greyish blue eyes and I’m just under six feet.

But as I was saying. Blips.

There was one night at the bar (that is walking distance from both of our houses) when we were both there. I saw her and stopped to give her a hug and we shot the shit for awhile. We were both fairly tipsy at that point so maybe it was a little flirtatious but it wasn’t weird. Anyway I went to go to bathroom, and I came back to my seat. That’s when one of the guys who was sitting at the table with us, Stew, who we both knew from some place or another and who was definitely past the point of tipsy gave me a soft punch in the arm and slurred together

“Hey man. She just said you are hot.” While pointing to Kelly who was blushing severely.

“Shut up! No I didn’t! Stew, you’re drunk!”

It was funny to see this forty something year old acting like an embarrassed middle schooler and I kind of enjoyed it and milked it. I gave Kelly kind of a smirk.

“Well even if you didn’t, I’d call you hot, so no harm no foul.”

She laughed and the night went on with out any awkwardness. But like I said. Blips.

Fast forward to about a week ago. It was a Thursday night and I was off on Friday so I figured I’d walk over and have a beer with Kelly and say hi to their now 13 year old, Jessie. I knocked on the door and was met with a smile.

“Hey Sam!”

Kelly is an average height for a woman, maybe about 5’4”. She has shoulder length black hair that is graying just enough that you can tell, but she wears it well. She keeps herself in good enough shape, especially since Grants passing, but is on the thicker side. She fit well in her jeans. If she wore a deeper v cut shirt it would be distracting. Overall, a very cute middle aged woman.

I sat down at the dining room table.

“You want some wine?”

She was already holding her own glass In her hand.

“Don’t you know that I only come here to bum booze from you?” I said with a laugh.

She rolled her eyes.

“I shouldn’t be so giving.”

Jessie was sitting in the next room watching TV so I stuck my head in and chatted with her while Kelly poured me a glass. I didn’t bother her too much, since she was a thirteen year old watching TV, but it’s always good to see her. She’s such a sweet girl.

“I hope you like Chardonnay.” Kelly said as she handed me the glass.

“Well I see that the only other option is Fireball so this will do.” I said as I gestured to the top of the fridge where she had grabbed the bottle of wine from.

“What?! No shots?” she mocked.

And then we proceeded to talk like old friends and lost track of time. And poured a few more glasses of wine each. Jessie had since gone to sleep and some of the topics were a little spicy. We actually got to talking about my most recent previous “relationship”.

“I don’t understand it Sam. Becca was a beautiful girl. Why end something like that?”

“Because that’s just it. She was fun to look at. But I couldn’t sit around and talk with her for two hours like this. I would hardly call it a relationship. I think we both really liked having sex and that was about it. Not the most solid base for a lasting relationship.”

“I guess that’s fair. But you shouldn’t be alone.”

I laughed.

“Are you hitting on me?”

She slapped me on the shoulder.

“Stop it. I’m just saying I worry about you.”

It got serious for a second. It hit me why she was concerned about me being alone.

“Yeah well I worry about you too. How are you doing?”

And then we got into a conversation about her last couple of years since the heart attack. She cried a little bit. Not full on sobbing cry, she just shed a few tears when the conversation got the best of her. Weirdly enough, I thought she was really pretty when she cried. I don’t exactly know why. I think maybe it was because this woman wasn’t angry. She didn’t hold resentment towards life or God or whatever. She was at peace with the suffering that she faced. She was just sad.

“You know I’m always here to drink wine and talk shit with.” I said.

She, being the way she is, cracked a smile and lightened the mood.

“Thank god for that. And thank god that I work from home now because I may be a little hung over tomorrow.”

“Is that you kicking me out so you can sleep?”

“Yes, yes it is. You pick up hints so well.” She replied with a smile.

I stood up and put my glass in the sink and she followed me to the door.

“I’m glad I live close enough to walk.” I laughed, a little wobbly from the wine.

“Me too. Thanks for coming over tonight. Really.”

I gave her a hug like I had many times before.

But this one lingered. So I let it, and squeezed her a little extra tight.

“Sam how drunk are you?” She whispered.

Um what was she doing?

“Sober enough to know I don’t usually hug you this long. Drunk enough to not care.”

“Perfect.”

She pulled back and kissed me softly on the mouth. I kissed her back. There was no tentativeness from either side, like we both weren’t surprised at what she just did, even though I was. She pushed me against the door softly and we made out like that for probably 30 seconds.

She pulled back.

“I’m not exactly positive I should have done that but it was fun.” She said with a little smile.

“Hey I didn’t mind.” I said back softly. “Have a good night Kelly.”

“You too.”

She closed the door behind me.

My mind did race a little bit on my walk home but by the time I got to my bed the wine had done enough to me that I passed out fairly quickly.

I woke up at about 8:30 and rolled over and saw a text from Kelly.

“Hey. My lunch is from twelve to one. Can you come over here? I need to talk to you about last night lol. I’m sorry if I made you uncomfortable.”

“You didn’t at all Kelly. If anything I kinda felt guilty as if I took advantage of you being vulnerable. But yeah, I’ll be over there. You want me to bring you lunch?” I typed.

A few minutes later my phone vibrated.

“Chipotle please :)”

At about 11:50 I knocked on her door. She answered it while talking on her headset to someone at work. She was a dispatcher, so working from home actually made a lot of sense for someone like her even before the virus hit.

A few minutes later I heard her telling whoever that she was taking her lunch hour and she turned off her headset and came and sat down and ate with me.

“Thanks for the food. You rock.”

“You’re damn right I do.”

She smiled.

“Okay Sam so seriously, I’m sorry about last night. And I’m not sure apologizing is the right way to go about it because I’m not really actually that sorry, and judging from your reaction I’m not the only one who’s had a little crush. But between the vulnerability and the alcohol I want you to know that you definitely didn’t take advantage of me and I’m sorry if what I did made you feel weird or awkward.”

“It didn’t. Honestly Kelly, it was kinda hot how you just did it and didn’t overthink it. Women aren’t usually like that, even though I know the alcohol probably helped your confidence. I just didn’t want you to think that that’s what I was here for or that I just played along cause I was drunk.”

“So you’re saying you’d have done it sober too?” She joked.

Then in a span of about two seconds I got a mischievous idea and contemplated it. And made my decision.

I grabbed her face and kissed her on the lips. And I wasn’t shy about it. I opened my mouth a little bit and her tongue came out to play immediately. After about 20 seconds I pulled away.

“Does that answer your question?” I said, with a fake snap in my voice.

She laughed.

“Yes, I guess it does.”

Then we kind of just looked at each other smiling. There was tension building. In my “travels” I have learned something. Women love when guys are bold. When they have a plan. When they know what they are doing and don’t hesitate. So instead of letting it get awkward, I grabbed her hand and pulled her with me and she followed. I laid down on the couch and pulled her on top of me and we proceeded to make out like teenagers. It was so much fun. I was squeezing her ass while she bit my earlobe and kissed my neck. And then I took my turn exploring her jaw and neck with my teeth and my tongue. And honestly I really only intended on this teenage make out session. She was only on her lunch break, after all.

But I was very obviously hard. I wasn’t trying to hide it. And as we were making out she rolled up on her side a little bit and all at once put her hand right on my cock.

“Is this for me?” She whispered in a low voice, with a smirk.

I then turned myself sideways so we were both laying on our sides on the couch and reached between her legs and cupped her pussy with my hand.

“Only if this is for me.”

She moaned a little and then kissed me again hard.

I rolled off the couch onto my knees beside the couch. She looked at me, confused. I made her sit up and positioned myself between her legs. Then she smiled at me, catching my drift.

“Take your sweater off.” I said.

“I’m not wearing a bra.” She replied.

“Perfect. I suck at taking them off anyway.”

She laughed and peeled off her sweater. I began to kiss her neck and slowly worked my way to her right nipple, which I began to lightly suck and bite on, while using my other hand to pinch the other one.

She softly moaned and cooed and I could feel her melting back into the couch. I took my time with her tits. She seemed to be enjoying every second.

But I did have a second destination. She was wearing a pair of shorts so as I began to kiss her stomach I tugged on them a bit and she picked up her butt and as I pulled them off she straightened her legs and they came off easily, almost as if we had done it before.

And she was going commando!

I laughed, and then she did too, knowing why I was laughing.

“I just really am not the biggest fan of underwear.” She said.

Then she pulled on my shirt so I took that off too. I kissed her again and pushed her back into the couch. I was still on my knees on the floor positioned between her legs as she sat upright on the couch. I pulled her legs up so that they were resting on my shoulders. I then proceeded to bite and lick her inner thighs, going back and forth to each one. I would get close to her pussy, and then miss it with my tongue by centimeters and go to the other thigh. It was working. Her scent was intoxicating and it was getting stronger and she was beginning to pull me into her with her legs. Finally, as I was licking up her thigh, I let my tongue rest on the top part of her pussy. She sighed a long sigh. I then began to make circles with my tongue until I found her clitoris. I began to lightly suck on it, and then went back to tracing circles around it.

“Mmm, Sam. That feels so good.”

After a minute, I began flicking my tongue over her clit, and moved my hand up and slowly put my index finger inside of her. I got my first very loud moan.

“Shit!”

I began to go in and out with my finger while going back to the circles with my tongue.

“Oh my god, Sam. Please don’t stop.”

I didn’t. I kept going exactly as I was and I felt her legs begin to squeeze my face. Then she moaned loudly again and squeezed me super tight and bucked her hips hard. I made it a point to try and keep my mouth on her clit through the entire orgasm. Finally, she pulled me off of her and I wiped my wet mouth on her inner thighs.

She pulled me up and kissed me aggressively. Almost as if she wanted to taste herself on me. It was so fucking hot. Then she pushed me back and made me stand up and slid off the couch so she was on her knees in front of me. She kissed my stomach and began to rub my cock as she looked up at me, smiling.

“You are really good at that.” She said.

“I’m glad you think so.” I replied

She pulled my shorts down and my cock sprung free.

“Mmm.” She licked the drops of pre cum off the tip of my cock.

She then spit on it and began to use her hand to make it wet. And then she started to lick it from the bottom to the top several times, clearly intent on getting it nice and wet.

I moaned.

“You’re fucking hot Kelly.”

She looked up at me and smiled and then at that moment took my cock into her mouth. She bobbed her head up and down and took me as deep as she could. It felt incredible. She took my cock out of her mouth and looked up at me.

“I want you to come on my tits. Pull me off when you’re about to come. You can push my head down a little until then though.” She smirked.

Fuck.

She took me back in her mouth and grabbed the base of my cock with one hand and softly grabbed my balls with the other. She began to move up and down with her hand and her mouth. I put my hands on the back of her head and did as I was told. I softly followed her lead at first, not really pushing her head, just moving my hands with her head. But as she got going I began to take the lead. It was so hot. She was making theses sloppy noises as I pushed her down onto my cock. I could hear her moaning too. Because she had her hand around the base, me pushing her down onto my cock wasn’t uncomfortable for her at all. She knew what she was doing.

As I watched her simultaneously jerk and suck me off while also pushing her head down onto me softly, it began to be too much.

“Mmmm, Kelly.”

I kept pushing her down. I didn’t want this to end.

But I pulled her off and held her head in my hands and stared into her eyes while she jerked me off quickly, aiming my cock at her tits.

And I came hard. I moaned loud. I covered her tits with my cum.

Suddenly I felt her mouth on my cock again. She was licking me clean.

Finally I collapsed on the floor next to her.

“Holy shit.” She said. “That was fun.”

We made out again.

Suddenly I thought of something, and looked up at the clock.

1:07.

“Shit Kelly. You’re late for work.”

“Dammit. You’re right.” She laughed, as she hurriedly put her clothes back on. “I hate to kick you out so quick though.”

“It’s okay. Wanna have some wine tomorrow afternoon?” I said with a little grin.

“Definitely.” She said, as she put her earpiece back in and turned on her computer.

As I walked home, I couldn’t help thinking that this is probably not what Nate meant by “checking in” on his mom.

Source: reddit.com/r/gonewildstories/comments/mali4v/checking_in_mf