Risky Friend with Benefits Pt. 01

This is story #24 of my series about my post-marital sexual journey. Read the first story (Babysitter Lauren) or my profile, for any background needed. You may see references to prior stories/people, but for the most part each story stands on its own.

Not everyone likes me or my stories. That's OK.

I enjoy all comments

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High school football is big in my town, and just about everyone goes to the games on Friday nights. It's a big social event. My kids went to all the games, it was a great way for kids to blow off steam at the end of a long week at the beginning of a new school year, so they all ran around and socialized the whole night.

I went to most home games, since I knew many of the players and their parents. I typically stood off to the side, rather than get mixed up into the large crowd of parents and other adults in the center of the bleachers. I would still socialize if I saw someone or someone saw me and would walk down toward the end of the bleachers to chat, but generally, I prefer to be off to the side by myself and not in a big crowd.

At one particular game early in the season, an old neighbor of mine, Kim, spotted me and waved down to me, then later walked down to say hello in person.

I knew Kim because she lived just down the road from my then-wife and I. When we first met, she was 26 years old, and she and her husband had just had just moved in with their one-year-old baby. I didn't particularly care for the husband, Josh. He was a local cop and thought that he was cooler than ice, but he was really just a pompous ass.

Despite their age differences, Caitlin and Kim hit it off. Kim grew up about an hour away. She didn't have family or friends in the immediate area, and so she and my wife fast became BFF's. Kim was around quite a bit since my own kids were very young, so they all became very close as the years went by, and Caitlin invited Kim to join their very exclusive, i.e. snobby book/gossip club.

Now seven years later, Kim and Caitlin are still very close; best friends in fact. Josh cheated on Kim and she dumped him about three years prior to this night at the football game, and they had had another baby prior to that. She still lived in the same house, as did Caitlin, and they spent a lot of time together.

It was no secret that Kim, now 33, wanted to get remarried and have more kids. She always talked about wanting a houseful -- four or five kids. She had dated some guys since her divorce, but I guess no one worthy of being a husband and father.

"Hey stranger!" Kim said as she approached.

We hugged hello as we typically did. Kim and I got along fine, really well in fact. She didn't take any sides in my divorce, and I still saw her around because our kids were friends and went to school together.

I actually felt that Kim and I were a better "friends" match than Caitlin and Kim, because we got along so well. Kim could be crude and talked like a frat boy at times, and that kind of language typically turned Caitlin off.

After a few minutes of general chit-chat, Kim asked, "So, how's the dating scene?"

At this point in time, my public relationships post-divorce were Denise, Kelly, Susan and Stacy. My other relationships and various hook-ups had been kept under wraps and low key, so very few knew about the other situations that I had been a part of.

I liked Kim, but wanted to tread carefully here. She may not have been fishing for information, but since she and Caitlin were close, I was careful about everything I said.

"Eh, slow. Enjoying being single for the time being. How about you?"

"Same, slow," she answered. "The last guy I went out with was a real piece of work. Told me he lived in some real nice house that was being remodeled, so we never went there. Turns out he lived with his mom! Total douche bag."

I laughed. "Some guys will say anything to get a piece of ass."

"Yeah," she answered with a smirk. "I have a new rule. No pussy for you unless you live alone!"

Jokingly, I said, "Hey, I live alone. If that's the only standard, then what are you doing after the game?"

She playfully slapped me on the arm and said, "Very funny. Although I'll tell you, some of the book club girls have suggested to me, not with Caitlin around of course, that you and I should date. Could you imagine?"

"Oh, that would go over like a lead balloon," I said to her, chuckling. "I get enough shit from her, that would be like a nuclear bomb."

"Besides," I continued, "you want more kids, and me, for one, I don't, and for two, that issue has been taken care of, if you know what I mean."

"Oh, believe me," she said, "as much as I like you and think we'd probably get along great, that is an absolute "no" for me too. She'd have a fit; and worse, I'd get thrown out of book club!"

"Well, then it's settled," I said, "no dating, just sex."

She slapped me again and said, "you wish."

I laughed again and said, "You wish too, believe me."

We turned our attention back to the game for a few minutes, the conversation pausing as a few folks walked by us.

When we had some privacy again, Kim said, "You know, it's not really a crazy idea."

"What isn't, us dating? Are you nuts?"

"No, I mean the 'no dating, just sex'. We're both single and not seeing anyone at the moment. We know each other well so there's the familiarity factor. I mean we couldn't ever let anyone know, so we'd have to be really careful, but other than that, what's the downside?"

I was pretty shocked at this turn of events. I had always found Kim to be very sexy and always thought she'd be a wild roll in the hay. Kim was on the shorter, stockier side. Very pretty with a great smile, nice big tits. She was bit on the thick side, her ass shapely but big, with thick thighs to go along with it.

"Can't really argue with you there," I said. "Are you serious about this?"

"Yeah, I mean why not?" she answered. "I'll be honest, it wasn't even a thought in my mind until two minutes ago. But after you said it, I thought to myself, 'He's really hot, I know from Caitlin that he's very highly sexually charged so he'd hopefully be able to keep up with me, and if the rumors are true, his dick sounds like it's pretty damn big, and I've had nothing but puny dicks for the last three years.' So yeah, I am serious about it. What do you think?"

I looked at her and said, "Well, I'm already fucking you in my mind, so I guess that's a 'yes.' What do you have in mind?"

Kim looked at the scoreboard. The first half was just drawing to a close.

"You have your kids this weekend?" she asked.

"No, they are with Caitlin until Sunday evening. You?"

"Yes, this is my weekend, but Josh is here. They are sitting with him, so he can keep an eye on them for the rest of the game. I'll tell him I'm not feeling well and ask him to drop them off after. That gives us about an hour and a half. Meet you at your place?"

Kim knew where I lived since her daughter had been over to play with my kids several times.

"Works for me. I'll sneak out the back gate so no one sees me leave. If anyone sees both of us leaving, that will be sure to start rumors."

"Sounds good," she said. Then, "Are we really gonna do this?"

I looked at her and responded, "I'm totally into it, but the risk is real. A divorced guy fucking his ex-wife's best friend is so cliché, and if she ever finds out it will be real trouble. So, if you're gonna back out, do it now. I'd rather watch the end of this game than go home and be alone with my dick in my hand."

"Fuck it," she said. "Let's do it."

"Atta girl," I said with a smile.

Fifteen minutes later, Kim was letting herself into the my house through the back patio door. She had parked in a back corner of the lot to conceal her car. I lived in a townhouse development which never got any through traffic, and none of my neighbors in this small development was anyone that was a common acquaintance of Kim or Caitlin. But still. it was smart to keep her car out of sight.

I met her in the lower-level hallway area, a space that included my man cave and kids game room. Kim had been to my house various times before so she was familiar with it. We went up the first level of stairs to the living room and kitchen, and I offered her a drink.

"Some pinot grigio if you have any," she requested.

I handed her a glass and we sipped together, clinking our glasses together first.

"What are we toasting to?" I asked as we sat on the sofa.

"Well," Kim said, "In my case, I'm toasting to a four-month sex drought about to come to an end. How long has it been for you?"

My last public relationship (Stacy) had ended in January, about ten months prior. Since then, I fucked my married work partner Jen for about three months, plus Brandi, the Hispanic single mom who I gave some furniture to, plus Carol, whom I fucked about ten times over the course of about a month, the relationship ending just a few weeks prior.

I didn't want to admit to my male slut activities over the last ten months, but Kim likely wouldn't believe that it had been that long for me, so I simply said, "about the same. I started seeing an old friend from high school who lives about two hours away, but it was too much. That ended over the summer."

A thought occurred to me, something Kim had said earlier, so I pressed her.

"What 'rumor' were you talking about earlier. Something about puny dicks?"

She laughed, "Oh, that. Yeah, well way back in the day when you and Caitlin were still married, at book club one night we started talking about dick size. Kara (one of Caitlin's single friends) had started dating a guy and she said how big his dick was, like seven inches. Then Caitlin blurts out, "is that all?"

"We all looked at her like, 'what do you mean, 'is that all?' How big is Phil?' And she goes, 'eight and a half'. No one else believed her, but I remember thinking, 'Yeah, I can see that."

"Then I was talking to Susan (Kim was also friends with her, which I had kind of forgotten about) soon after you guys split up and asked her what happened. She said you guys weren't really compatible, personality-wise. And she said it was a damn shame too because your dick was so big and she'd love to have it all the time."

Kim took a big gulp of her wine, finishing it.

"And now," she said as she sat her wine glass down and stood up, "I get to see, and feel, for myself if they were exaggerating or not."

She held her hand out and I took it, standing up next to her. I towered over her by a foot, and I leaned down to kiss her, our mouths opening immediately and tongues dancing in a surprisingly familiar way.

Our mouths parted, and the look in her eyes matched how mine felt. This was going to be some high-quality sex.

I whispered in her ear, "Is there anything you don't like?"

"Nothing," she whispered in response. "After a kiss like that, you can do whatever you want to me."

Her hand went to the front of my shorts as she spoke to me, and I could see in her eyes that she was pleased with what she felt.

"Let's go to your bedroom, we only have about forty-five minutes. I can't wait another minute."

Hand in hand we walked back to my bedroom. Kim and I were dressed similarly, me in shorts and a golf shirt, she in shorts and a light t-shirt with our school's logo on it. As soon as she entered the bedroom, she spied the large mirror on the wall opposite the bathroom door.

"Oh my," she said. "I'll bet that mirror gets a lot of use."

We stopped and kissed again, and our hands immediately went to the other's shirt. I lifted hers first, and she held her arms up to allow me to pull it over her head. The bra she was wearing barely contained her giant tits, and within another five seconds, it joined her shirt on the floor. Her tits were magnificent.

My shirt came off next, and then we each took off our own shorts. Kim's hand went right between my legs, and she squeezed my shaft with purpose.

"Oh God Phil, I'm sorry, I want to suck you, but I need this inside me right away."

No need to apologize, I thought. I'm happy to get to the main event. I had a feeling we'd be exploring each other in many ways over the next few weeks, assuming she didn't change her mind after this first night.

Kim threw herself on the bed and opened her legs invitingly.

"Please just fuck me. Everything else can wait."

Like I said, Kim was a little plump. Shorter with thick thighs and a pretty wide ass, but she was very sexy -- very pretty with a great smile, and her pussy looked great.

I dove between her legs and took a long lick of her pussy just to get a taste, and I wasn't disappointed. Very tasty and fresh, and I looked forward to a long pussy eating session with her soon.

Kim was impatient though, and she grabbed me by the hair and pulled me up to her.

"I said fuck me," she said as she reached down to grip my cock in her hand.

I sat back on my knees and watched Kim rub the engorged head of my dick along her slit. After a few trips up and down, she poised my cock head at her opening, and looked right at me.

"Do it," she demanded.

As is my nature, slow and gentle wasn't in the cards. I sank the full length into her in one violent thrust and watched as my cock disappeared into her warm pussy. Kim's mouth opened in a silent groan, her eyes rolling back in her head as she arched her neck back. The silent groan grew louder and louder as I held still in that bottomed out position for what felt like a full minute.

I held still in that position as Kim shook. She settled down, then looked at me, her eyes dark.

"God that was good. Now, start fucking me."

Kim grabbed ahold of her feet and pulled them back, really exposing herself to me. She looked great as I sat back and pushed on the backs of her thighs. Then leaned forward and started thrusting, faster and faster. Kim's glorious tits bounced up and down, and her head rolled from side to side as I pounded her.

"Yes," she cried lustfully, "Fuck that pussy."

She let go of her feet as I hooked her knees behind my elbows. One hand went to a tit and the other to her clit, and I watched her pinch a nipple as she furiously fingered herself.

"Fuck, I'm coming. Don't stop, please don't stop."

Kim groaned in orgasm as I continued pounding her. I slowed a bit as she came down, and my pace became steadier. I had planned to flip her over and finish doggy style, but those tits were making me crazy.

"I'm gonna come," I warned.

Kim nodded, "Yes, do it, come in my pussy," and after a few more intense strokes, I thrust myself into her as far as I could and started flooding her pussy with cum.

Kim dropped her legs as I let them go, and I fell forward onto her.

Her lips went to my ears as she whispered, "Oh yes, I can feel your cum shooting into me."

I held still as I finished my orgasm, Kim's fingernails digging into my shoulder blades as she held on tight.

"Holy fuck," she cried as we flopped back on the bed, "that was fucking great."

We laid silently for a minute, catching our breath.

Then Kim's phone buzzed, and she grabbed it. She turned to me with a smile.

"Great news! Game is going to overtime, and Josh said he'd take the kids for ice cream after, so we have some more time."

Kim slipped under the covers as I refilled our wine glasses, and we reclined on my bed, sipping our drinks. We spent some time getting me caught up on the old neighborhood, then turned to some book club gossip.

"Oh, how'd I'd love to tell the gang that the rumor is true," she said, glancing down at my crotch. "But I guess that secret will have to stay in the vault."

"What else did Caitlin tell you?" I asked. "Is there anything else you need to confirm?"

She laughed, saying "She shared some of your kinks with me, I told her I thought a lot of them sounded fun. Then toward the end as things were getting bad, she said you wanted too much sex. I asked if your sex drive had increased, and she said no, she just didn't want it as much. So, I said something like, 'well, maybe it's not that he wants it too much; maybe you don't want it enough.' That didn't go over well. She didn't talk to me for a month."

I laughed, "Well thanks for sticking up for me. Didn't work though, obviously."

"No problem. She's crazy by the way. Everyone knows what a great guy you are, great dad, super-hot. We all think she's nuts for letting you get away. And with this dick, she's extra crazy."

"Aw, thanks. So, now that we're just chilling," I said, "I'm curious the kinds of things you like and don't like. It's always fun to learn about someone's preferences as you go along, but since we're friends, let's play a little twenty-questions rather than figure it out as we go."

"Sure," she replied. "Go ahead, shoot."

"Ok, let's start with the obvious. Oral. Giving first."

"Oh yeah I love to give head," she said. "I would have done that first but I was overanxious and thought we were short on time."

"Can you deepthroat?" I followed up.

"Yeah, I can. It will be a struggle with you though. Josh was almost seven inches so you've got an inch or so on him, but once you get past the gag point, the length really doesn't matter. It the width, plus that oversized head of yours. I'll do my best."

"What about getting oral, I assume most women do but some don't."

"Are you fucking kidding?!?! I love to have my pussy eaten. You can munch my box all night long if you want to!"

"Great! What about 69? You like that?"

"Mmmm yes, I love it! Especially with the guy on top."

"Same," I replied. "And I love to have my face sat on and smothered, so I like it either way too."

Kim laughed, "So you want me to sit on your face and smother you? Be careful what you wish for. These thighs and this ass could be a problem."

"Trust me," I said, "it will NOT be a problem in the least."

I continued, "What about cum? You like it in your mouth? What about on your tits?"

"Oh, I have no problem with cum; in my mouth or anywhere else. I'm a swallower for sure. It felt like a huge load you just put in me. I would have swallowed every drop. I wish I had known we'd have more time, I would have had you pull out and come in my mouth or on my tits so you could go down on me in round two."

"Well, there's something about me that you should know then. I have no problems with that. I'll eat pussy with my cum in it, and kiss you with a mouthful of cum. In fact, I usually go down and do a creampie cleanup after sex. I love it."

"Wow really?" she said. "Caitlin never mentioned that!"

"Yeah," I said. "That only started after the divorce. She would have been repulsed by that anyway. She hates cum."

Kim laughed, "Yeah, I know. We all know. That is no secret amongst the book club."

"But," she continued, "I love it."

Kim reached over and grabbed my drink from my hand, then set it down on the nightstand along with hers. Throwing the covers off, Kim opened her legs and ran a finger up and down her slit. Slowly she slipped a finger inside of her, wiggled it around, then pulled it out glistening with my cum. I watched as she slowly slid that finger into her mouth.

She removed her finger and slid it back between her legs, and I moved in to kiss her and sample the sweet taste of our combined fluids. Kim's finger joined our tongues a minute later, this time holding a large wad of cum that she had pushed out and scooped up from her dripping cunt. Together we licked her finger clean of cum, both of us moaning in unison.

I turned my head and whispered in her ear, "get up here and plant that sloppy wet creampie on my face."

Kim moaned lustfully again as I said this, and positioned herself above my face, hovering over me. She poised there, cum slowing losing the battle with gravity and starting to drip out of her cunt. She lowered herself just a bit more, close enough that I could just get my tongue up onto her outer folds.