Risky Friend With Benefits Pt 02

This is Part 2 of 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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Kim and I continued to get together when we could, maybe six times over the following three months. There are two occasions that are very memorable.

One day in early December, I got a text from Kim, late afternoon -- "I need you. Tonight. Can you meet me?"

I had my kids staying with me, but they both had religious education that evening, so I would have about two hours free. I knew that Kim's kids went as well.

I replied, "Absolutely! Wanna meet up at my place during CCD?"

"No," she answered. "My place. Josh is picking kids up and taking them to class. Drop yours and come over, just pull into the garage."

"See you then," I answered.

"There's a catch," she said. "I have my period. I'm insanely horny. Is that a problem?"

"I have no problems when it comes to sex, except anything that involves me touching another guy. See you around 6:30."

I had no problem with period sex. I'd done it plenty of times prior to meeting my ex-wife Caitlin, so it wasn't an issue. Caitlin though never let me touch her when she had her period. I knew some women got really horny during their time of the month, while others felt bloated and disgusting. As a man, I couldn't relate, so I certainly never had any reason to judge.

I arrived as scheduled. It was dark by 6:45, and pulling into the garage I had little concern of Caitlin spotting me pulling into Kim's driveway, if she happened to be driving by at that moment.

I let myself into Kim's house and called out. I found her in the living room sipping a glass of wine. She was in a light robe. As soon as she saw me, she stood up, grabbed my hand and marched me toward her bedroom.

I entered her bedroom and saw that she had taken the comforter off and threw some old towels on the bed. Kim dropped her robe as she moved toward her bed, her big ass jiggling in a thong as she walked, then she laid down on the towels and put her head on the pillows.

I stripped down -- I was only wearing sweats and a tee shirt -- and climbed on with her.

"Let me suck you," she said, so I straddled her head.

Kim inhaled my cock, sucking it deep into her mouth and pulling me forward with her hands on my ass. I fucked her face like this for a few minutes, loving the telltale sounds of my cock passing in and out of her throat. Eventually I pulled out, and a huge glob of mucous fell from Kim's mouth onto her chest as I did. My shaft glistened with saliva, and I scooted back, pushed Kim's big tits together and fucked her tits as she forcibly spit another wad of saliva between her tits and onto the head of my dick.

"I love these big fucking tits of yours," I told her.

"Well, they love your big dick too. I'd love for you to come on them so I can rub your cum into my skin, but I need you to fuck me in the worst way. I get so horny on my period and I need your cock in me. Please fuck me."

I pulled my cock from between her tits, and Kim shimmied out of her panties, a bloody pad clinging to them. She spread her legs wide, showing me her oozing, open cunt. I rubbed the head of my cock up and down along the outside of her slit, then pushed the head of my dick inside her.

As soon as the head was in, Kim grabbed my ass and pulled me all the way into her. Her legs flew up in the air and she made a guttural groan as I buried myself into her. She shook with an orgasm the second I made contact with her clit as I bottomed out inside of her.

"Oh God that feels good, Jesus yes, fuck me, don't stop."

I kept up my thrusts, increasing in power and speed as we went.

Kim was fingering her clit like crazy as I fucked her. My shaft was covered in her blood as I pushed and pulled it in and out of her.

"I'm gonna come again soon, my clit is on fire right now," Kim cried, and sure enough she groaned again and shuddered with another orgasm.

I could feel myself getting close as well. I slowed my pace as Kim came down. She must have known that her next statement would prompt my next move.

Taking my face in her hands, she said, "My clit is so sensitive right now, I'm not sure I can take much more."

She knew from our prior time together that I never let anyone tap out, and asking only fuels my desire.

I pulled my cock out, covered with her blood, and ran my head and shaft up and down her pussy lips, each time running it along her clit as well. Kim scratched and clawed my arms and chest as I rubbed her overstimulated clit.

"Oh God, Oh God, Oh God," she cried over and over as the head of my dick kept tapping her clit.

With a deep desire, she said to me, "Please come on my tits."

'You like that huh, my cum on your tits? Why?"

"I love to rub it into my skin like lotion, it feels so dirty and naughty," she replied.

I kept up fucking her outer lips and clit with my shaft, a dozen or so more strokes, as Kim rubbed her tits, pushing them together and pinching her nipples, inviting me to cover them.

On an upstroke, I held still, then my cum shot forth like rocket. The first shot hit Kim on the chin, and the rest of my load covered her tits and stomach. She rubbed the cream into her skin as she moaned, my bloody cock hovering over her pussy as it slowly deflated.

"Holy shit that was good," she said as we came down from the sexual high. It's been forever since I've been fucked on my period. Thank you!"

"No problem," I replied. "Caitlin never let me fuck her during her period, so it was great for me too."

Kim leaned up and whispered in my ear, "I know. I'll do all of the things she wouldn't do."

This statement turned me on to the max and had me anxious for our next meeting....

I hopped in the shower quick and left to go grab my kinds from church.

A few weeks later, at Christmas, Caitlin was taking the kids to visit her parents for a few days, and asked Kim to keep an eye on the house and pets while she was away since Kim's kids would be with her ex. My kids spent Christmas Eve and Christmas morning with me, and then around noon they took off for the next two nights.

A bit later on Christmas Day, around 8:00 p.m., I was just putzing around my house, straightening up from the morning activities. My phone buzzed.

As she had done several months before, Kim sent me a picture of herself. This time she was under Caitlin's Christmas tree, wearing a Santa hat, and nothing else. Her legs were spread wide and her hand covered her pussy. Her big tits were exposed in all their glory.

"Merry Christmas!" her text read. "Come fuck me in your ex-wife's bed. Let's do all the things that she wouldn't do."

I laughed and responded, "Be right there. Let's drink her wine too!"

Again, I pondered Kim's statement about "doing the things she wouldn't do." Kim and Caitlin were close, and I know that Caitlin shared with Kim over the years many of my kinks and fetishes that she refused to do with me. I just wondered how much Kim knew.

I got to my old house about 15 minutes later. I let myself in and found Kim in the living room, sitting on my old sofa. She was wearing a nice silk robe and the Santa hat.

Patting the sofa next to her, she had, "Have a seat, I have a Christmas present for you."

I did as she instructed, then Kim stood in front of me and slowly opened the robe. She was wearing the skimpiest red lingerie. Kim danced around in front of me for a minute, and then with one pull of a string, the lingerie fell away, revealing Christmas bow-shaped pasties on her nipples, and a ribbon wrapped around her waist, with a large gift bow right between her legs, covering her pussy. I laughed as I reached out to peel the pasties off, then untied the ribbon, causing the bow to fall away.

I hadn't fucked Kim in about three weeks at this point. One time I asked her if she was always shaved bare and ever considered leaving any hair. She answered that she wasn't opposed to it, but liked the feeling of being bare as she went through her day-to-day routine. She asked about my preferences, and I told her that I didn't mind a little hair, either a landing strip, a shadow or even a small bush, just nothing that was overgrown or messy looking.

Behind the bow on this day was a neat little heart-shaped, dirty blond bush. I smiled as I ran the back of my fingers through it.

"You like?" she asked.

I nodded in response, "Merry Christmas to me!"

Kim smiled, then said, "I have something else for you. Stand up, and take your clothes off."

I complied, standing and removing all of my clothing. Kim had me turn around and put my hands behind my back, which she then secured with a zip tie around my wrists.

I sat back down, my cock already at full hardness. Kim took a length of ribbon and wrapped it around the base of my package - balls and shaft, then tied it into a tight knot. I could already see and feel my cock straining before she had even finished tying it.

The finishing touch was a gag and blindfold.

Caitlin was never been into bondage of any kind, either giving or receiving, despite my asking several times. Kim must have known that, and as her text said, she was going to do things with me that Caitlin and I hadn't done or that Caitlin would no longer do.

Once I was fully bound, unable to see, move or speak, Kim just started teasing me with her fingertips. She had fairly long nails, which she gently grazed up and down my shaft, lightly tickling my balls, running her sharp nails around the underside of my head and around the rim.

Occasionally she would grip my shaft with her hand and stroke me intensely for a minute, and then suddenly stop. She would also lean forward and lick just the underside of my cock head with the tip of her tongue, causing my cock to jump.

At one point she inhaled my length into her throat, just for two or three trips in and out, and then pulled back completely. Not being able to watch really heightened the feelings. Normally I'm very visual, but just listening and feeling became really intense since I couldn't see.

Kim used all of these techniques to edge me over the course of about twenty agonizing minutes. I wanted, needed so bad to grab her head and steer the action and get the relief I so badly craved, but I was helpless to do anything; I was at her mercy.

Kim finally reached up and removed the blindfold. My cock was throbbing; bobbing in the air as she teased me. My balls were literally blue from the ribbon, and my cock was turning a dark purple as well.

I begged her with my eyes. "Please, Oh God I need to come, please."

All to no avail. Kim continued, the teasing now having morphed into outright torture as she continued to manipulate my cock using a variety of techniques.

After ten more minutes, Kim finally relented. Gripping my cock with her left hand and squeezing tightly, Kim flitted the tip of her tongue just under the head of my cock. Like a butterfly, just very lightly, while she looked into my pleading eyes.

She did this for about thirty seconds, and then used her hand to pump my cock. After one pump, I let loose with a muffled groan.

My cum shot forth, higher and with more pressure than I ever remember. It rained down on us like a storm. My typically large load seemed to have doubled with the teasing and the pressure, and Kim delighted in the cum shower as shot after shot landed on her head, face and shoulders, then she leaned back and pointed the rest at her tits.

Kim untied the ribbon as I finished coming, and I could actually feel the pressure in my dick and balls being released, like a balloon being deflated. I'm not sure I had ever felt a more erotic mixture of pain, pleasure, relief and ecstasy all at one time. It was amazing.

Kim licked her lips and smiled wide as she watched the relief fall over my face, then she reached up and unhooked the gag. Straddling me, Kim attacked my mouth in a hot kiss. She was covered in cum, and our bodies rubbed against each other, smearing the semen across both of our faces and chests.

Kim sat back and looked at me, now using both of her hands to rub cum into the skin of her big tits, clearly something she loves to do.

"That was fuckin wild," she said. "I've never seen so much cum, holy shit."

"Perfect storm," I said. "I come a lot naturally, as you know. Plus, I haven't come in over a week, so I had some backup. And then you building pressure like that, it felt like I was packin' a fire hose!"

She laughed as she continued to massage her tits. When it was all rubbed in, she had me stand up so she could untie me, then she grabbed my hand and pulled me upstairs.

"We've got the place to ourselves for the next two nights," she said as I followed her bare ass up the stairs and into my old bedroom.

Kim flopped on the bed and wasted no time spreading her legs, her wet center glistening just beneath the light bush as she ran a finger up and down her slit. I jumped on top of her and kissed her as she fingered herself, then she moved her lips to my ears.

"Eat my pussy and make me come. Then lick my asshole and fuck my ass."

I couldn't believe it -- I was finally going to eat some ass and have anal sex in my martial bed, but with my ex-wife's best friend!!

I slithered my way down Kim's body, rubbing my face on her tits as I pushed them together, my scruffy goatee scratching her skin. She squirmed at this, and pushed my head lower.

"God, I'm so hot right now, I'm gonna cum as soon as your tongue touches my clit."

And I was hot to fuck Kim's big, glorious ass, so with that I dove between her legs, sucking on her cunt lips and pulling her clit into my mouth. True to her word, Kim exploded in orgasm, pulling my face into her even more tightly and releasing a nice flow of fluid, soaking my ex-wife's bed with her cum.

Wasting no time, I flipped Kim over onto her stomach, and she immediately raised her hips, presenting her ass and asshole to me. To date, in our half a dozen times together, I had only fingered her ass, but had not used my tongue on her or fucked her ass. That was about to change.

I pushed two fingers into her pussy, causing her hips to raise a bit more. I leaned forward and buried my face between her generous ass cheeks, and Kim moaned as my tongue flitted about her rosebud. She reached back to spread her asscheeks wide open, and I feasted on her ass like I was starving.

After a minute of tossing her salad, I rose up and straddled her thighs, my fingers still in her pussy, and my thumb replacing my tongue at the entrance of her asshole. I pushed my thumb forward as Kim thrust her ass back, and she swallowed the top portion of my thumb to the first knuckle easily.

A few thrusts later, and my entire thumb was buried in her ass.

Kim looked back at me and said, "This all feels amazing. I've been using small anal vibrators over the last few years to get off. I'm ready for a real ass-fucking. Be gentle and go slow, but do it. I'm ready."

Kim reached under the pillows and pulled out a tube of lube, obviously stashed there in advance. I loved her planning.

Now, gentle and slow isn't usually my style, and Kim new that. I grabbed the lube and applied a generous amount to my shaft as I jerked myself back to full hardness. I applied some to her asshole with my thumb as well, and it wasn't long until we were both ready.

I lined my cockhead up with her third input, as Kim looked back over her shoulder at me with a sultry, hungry look.

"Do it," she said. "Fuck my ass."

With that, I pushed forward as Kim thrust back. The head struggled to push through, but with a little extra pressure from me, eventually I felt the familiar "pop" of my dick entering her ass.

"Holy fuck!" Kim yelled. "You're gonna rip me in half."

"The worst is over," I assured her, though I have no idea if that was true or not.

Together we synched up our thrusts, and inch by inch my cock buried itself into her bowels over the course of about five thrusts. Kim's low moans grew louder and more intense with each thrust and each gradual inch.

Once I was fully buried in her ass, my abdomen pressed up against her generous ass cheeks, I pulled all the way out until just my cock head was still inside her, then slowly thrust it all the way back in. I did this about three or four times, and then again settled inside her, fully buried.

"You OK?" I asked.

Kim looked back at me again, and her eyes had a faraway look.

"This is so amazing; I never even considered the possibility that anal sex could feel so incredible. Keep fucking me, go harder and faster."

Given that green light, I did my thing, first grabbing her hips and really pounding into her. I pulled her hair by the roots and yanked her head back, and scolded her a bit.

"Fuckin' slut. What kind of a whore takes her best friend's ex-husband's cock in her ass in their old marital bed? You're a sick fuck."

I don't even know if she heard me, she was babbling incoherently as I sawed in and out of her. Kim's big tits were swinging and swaying with each violent thrust.

Finally, I felt my balls starting to boil. With my hands on her shoulders, I pushed her down flat onto her stomach and chest, then forced her head down and her face into the pillows. I repositioned myself so that I was driving down into her, and I fucked her without mercy.

Kim reached back and spread her ass cheeks, allowing me a full view of the penetration. It was too much. With a roar, I thrust all the way into her and unloaded into her rectum. My cum bubbled out around the seam as fast as I was shooting it into her.

I collapsed on top of her as she released her ass from her own grip. We laid there, me on top of her, her face still buried in the pillows. Slowly she turned her head to get some air and I eased off of her a bit. We were both sweaty, the skin on her back feeling clammy as she cooled down.

"Jesus Christ," she whispered. "That was intense."

My softening dick fell out of her with a plop and some gurling. I watched cum flow out of her and drip down toward her cunt before dripping onto the bed. Her hole eventually closed up, trapping my monster load inside of her.

I rolled off of her, and we laid in silence for a good five minutes, maybe more. I thought for a second that she had fallen asleep.

Finally, she lifted her head and looked at me.

"No one has ever fucked me so thoroughly and so well. You're like a machine."

She continued, "I'm sweaty and sticky and have dried cum all over me. What do you think about a shower in your old bathroom?"

I loved this idea, mostly because, in addition to how much I love to shower with women, Caitlin and I had never showered together in the current master bathroom. It had been remodeled to include a big sunken tub and nice big walk-in shower, but that was late in our marriage. She was over the couples' shower by then, and with our martial problems, she definitely wasn't into it.

But Kim was, and I was looking forward to soaping up those big, sticky tits of hers. The new shower had two showerheads. I had designed it myself, hoping to entice couples' showers with Caitlin, but as I said, we never got to use it.

I started the water flow and Kim and I stepped in. We kissed as the warm water flowed over us. I soaped up her luscious tits, thoroughly cleaning the dried cum off of her. I turned her around and did the same to her back and ass, making sure to clean the crack of her ass and her asshole as well.

Kim turned back to me, then dropped to her knees. She soaped up her hands and lovingly cleaned the anal sex and dried cum off of my dick.

Her doe eyes looked up at me and we both knew what was next.