How Does It All Sort Out? M/f

I'm not real sure sure that I would do things the same way if given the opportunity for a redo. I'm pretty certain I'd have made my play sooner.

I had been close friends with a woman for years, we were both single parents and would step in to help out when the other needed a hand. She had 2 girls she was raising and I had my son. We would get together for a big family dinner and catch up once every month or so. Overall it was a good friendship, but truth be told, she had a great ass that I caught myself admiring a little too frequently.

We will call her "Kat" and I am Dan. Kat, you see, is a handful. Late 30's 5'2" tall, broad shoulders from her years of swimming, that great ass I spoke of, and this amazing set of tits. Her long dark brown hair was curly and sexy, and her brown eyes brought out the natural color in her skin.

So anyway, one this day, Kat was over my place and the kids were off playing. We discussed some work stuff and she expressed some interest in my other activities. I told her about the lady I was dating, and I thought I caught a sense of interest... I moved on, stereotypically clueless as to the interest of a woman. A few minutes later, Kat steered the conversation back to the woman I'd been seeing.

"So, is this a serious thing or what? I mean, you've got to be getting ready to settle down at some point, right?"

"Well," I said "Yeah, eventually I will settle down, but this is extra curricular at best. We are both are looking for a good time, not a long time."

"What daoes that mean? If you're with someone you're WITH them, right?"

"Well, Kat, she likes to be a little... different. We have sex in public, and we like to go "push the boundaries" a little. We will go to a bar, and I will give her challenges she has to meet while at the bar."

"Huh? What do you mean challenges?"

"OK, so last night we were at Monte's and I ordered her a tequila sunrise and me a Maker's Mark on the rocks. I told her she needed to cum at least once before I finished my whisky. She leaned on the corner of the barstool I was on and rubbed herself off. She came three times while I sat there talking to the couple next to me."

"That's disgusting. How did they react?"

"Disgusting? no, it was fucking hot. She had grool to her knees! The couple I was talking to, they flat out asked her if she was OK. Then told me I had quite a night ahead of me."

"OK, I'll give this to you, the idea of doing things is public is hot. Rubbing yourself off on the barstool at Monte's is disgusting."

"Hahaha, Ok, Kat. What would YOU have done?"

"Made you use your hand."

"Ahh, but see, I told her SHE had to do it, that's the fun of it."

"OK then, I would have gone to the bathroom and used the stall."

"OK, but not as sexy as doing it right there in public. Just kind of the things, right?"

"I guess. But I don't see how that works into a routine thing."

"Oh, it's still new. We fuck a lot."

"Gross. You're going to get caught if you fuck in a bar."

"You're so uptight. The whole point is to ALMOST get caught. We went to Priscillas the other night and while we walked around, this little guy was watching her, she took him to the back and him play with her tits and she jerked him off. We were still in the store. On the drive home, I made her strip bare and play with herself until she came. Her punishment for cumming too early was going to be severe. She LOVED it."

"Punishment? like what?"

"Look, Kat, you sure you want to hear this? I don't want you to get any odd ideas. She's a fuck toy and we're both having fun."

W"Well, uh, yeah, tell me some more. I'm... just tell me what you mean by punishment."

"She likes a little pain, so her punishment was going to be 10 slaps on her tits. She came REAL soon, so I pulled over and slapped her tits 5 times each, till they were red and swollen. She came on the 9th slap, so she had to be punished even more. I put nipple clamps on and tightened them tighter than I've ever tightened them. She was creaming all over the seat of my Jeep. I swear the more it hurts, the turned on she gets."

"Yeah... OK, i see that..."

"Huh? What you like some pain, Kat?"

"Well, yeah. That sensation where pain blends with pleasure is hot."

We talked some more but then had to part ways for the day. I went to bed thinking about her ass and her unbelievable reaction to my experiences... I wonder if...?

I woke the next morning to do my routine, showered, shaved, dressed for work and decided ot check my email quickly. In it, I was amazed to find an email from my friend Kat.

"Dan, I think it's time to stop pretending. Everytime we spend a day together it feels comfortable and solid. You've never judged me and my situations, only ever been there as a support. I think it's time we gave "us" a shot. Yes, your stories about your lady friend helped make the decision, I spent most of the night touching myself wondering what you would do me to, WITH me... I think I can handle it. There remains one last hurdle for us, but I think you can handle it. Call me later."

I had a very busy day and no time to dwell on or wonder what was up with that last part, but I had a permagrin and walked through the day. As I was heading home, I dialed her number. "I was worried you wouldn't call..." she answered. "Who me,?" I stammered "I've been wanting this since that time we all went to the pool together and you teased me about your new tits."

"Yeah, I have a thing with flirting. About that day, did you notice anything else? It's rare but some do."

"Huh? no, I think I was distracted trying to pretend to not be looking." Now I was trying to figure it out. WTF is she talking about? Her terrible "semper Fidelis" tattoo?

"No big deal. Look, the girls are with their dad this weekend, Nic is in GA with his mom you said, right?"

"Yes, I drop him off tomorrow night"

"OK, I am going to a concert with a girlfriend, how about after the show I come by and we talk this through?"

"Perfect, for the record, I am fully on board."

"Oh honey, let's discuss that later"

That night I spent as much time with my son as I could, but the question was there, WTF is she talking about? The next work day was a blur and then in the car for the long drive to drop my son off with his mom. The typical exchange, and then the drive back with enough time to really start to wonder. I got one text early it said:

"Getting dressed for the show. I know you like thigh highs, but i HAVE to wear panties..."

And another one later:

"The opening band sucks, major let down. My friend says "hello, and and good luck!" hahahah!"

I had no idea what that meant. I continued my drive home and tried to concentrate on hydrating. It seemed like I may be performing later!

I got home, ate some food, decided to shower. In the shower I went ahead and shave my balls and shaft, clearing the area for a potential event. I'm not huge, hell just a tick over average, according to the internet. But that's fine, it's what I got, right?

After the shower, I put some music on and poured myself a whisky. It wasn't too much later that I got the text "OK, show over, waiting for traffic, then on the way TO YOU. Hope you're ready and still awake!"

I laughed to myself, if she knew how "ready" I was I'd be embarrassed. As I said, average sized cock, average sized man, but I swear, WAY more than average semen generation. My cock drools like a teething toddler (that's a lot). I can soak underwear in minutes and create an embarrassing spot through jeans. It's lubes shit up, and makes for a fun time when in use, but it can be a little difficult to explain away. As always while preparing for an evening, I drank water to stay hydrated, pineapple juice, cause of the internet stories, and whisky, cause I wanted to have a buzz on. :)

I puttered about the house, making sure it was tidy and looked nice. I sipped my whisky and enjoyed my music, and very soon I heard her car pull in the drive. She let herself in and I looked her up and down. She looked absolutely amazing. Her dark brown hair was flowing and curly and framed her pretty face. She was wearing a beige blouse and tight blue jeans and the boots! Ohh, the BOOTS were the thigh highs she was talking about, OK. Her blouse hung a little lower than I think it should have, as it covered her waist and ass.

She walked up to me and we awkwardly hugged. Having gone from friends to that next step we were both... awkward.

She tilted her head and we shared our first kiss. Our tongues danced and she pulled my face to hers as we explored. I let my hands fall to her ass and massaged her, pulling her towards me. She pulled back and licked my lip.

"Not here. Come on." She pulled me upstairs to the spare bedroom. The lights were off, it was dark, but not so dark we couldn't see one another's features and reactions. She pulled me in close and ran her hands up my chest to my nipples.

"I'm nervous, but you've never judged me before, so I trust you. I want to suck your cock, I want you to cum for me. Then I want you to eat me until I cum for you... We can discuss more later, but we need to get this out of the way."

Now, I'd heard from others about Kat's abilities. But I was not and i mean NOT prepared for the skill, the intensity, and the pleasure when she sucked my cock. That woman LOVED on my dick. She slobbered on it, stroked it, slapped her face with it, licked it, sucked it, teased it and just plain ENJOYED it. She moaned on it, gagged on it and really, it was as close to cock worship as I have ever experienced. She kept me on the edge for a while, but at one point she pulled my dick from her mouth and just stroked me. She looked up at me and said "your dick is drooling so much. You taste fucking awesome. I've never had someone make SO much precum that you fill my mouth over an over. I fucking love your cock..." And then she went back to sucking it...

When she'd had me at the edge long enough, or maybe when she was just ready, she kept me in her hot, wet mouth for longer, teased the frenulum with her tongue and played with my balls. I arched my back and shot into her mouth, which made her moan, which felt good, and I kept shooting into her mouth. She sucked me dry, released my cock with a slurp and pop and swallowed again.

"Jesus, that's fucking good. I'll need some more soon...." She was still wearing her club outfit. She crawled up the bed next to me, and started pulling her blouse off. It was dim in the room, but when she pulled her bra off and her glorious tits were revealed I almost dove on top of her. She kept me on my back, as she played with her tits, pulling at her nipples...

"So you said you like challenges, and some "extraordinary" stuff. I have a challenge for YOU, now. I want you to take my pants off and make me cum. I don't cum easily, and if you can't make me cum, this will never work between us. Are you "up" for the challenge?"

"Fuck yes, I am." I got up, flipped her onto her back and attacked her nipples with my mouth. I sucked them, slurped on them, suckled then and chewed on them. When I used my teeth a little, she squirmed and arched her back. Another woman who likes a little pain...

I crawled down and unzipped those glorious boots. As I did, she arranged some pillows so she could see. "I'm visual" she said "I like to see it as I feel it." OK, that's way hotter than laying there with her eyes closed.

As I pulled her boots off, I noticed something about how she lay, I wasn't sure what, and it wasn't bright, but I thought I saw a wet spot through her jeans. Jesus, if I get a girl who can make literal PUDDLES of juice, I have found my wife. I pulled her boots from her legs and feet and tossed them aside, I crawled up and unbuttoned her jeans, which elicited a sharp intake of breath from her.

As I pulled the seams open to her designer jeans she arched her back, freeing me to be able to pull them from her shapely ass. I pulled and tugged and get the below her ass, her panties came with the jeans and as I leaned in to pull them down off her legs, her cock popped up from where she'd tucked it and hit me in the face.

"Well there's your challenge."

I was agast, I could SMELL the pussy juices, but there was a cock in my face. "Wha... But you gave birth to two daughters...."

"Yes, I'm a woman. With a cock, Dan. I have all the girl parts and one cock to go with it. It's call-"

"I KNOW what it's called, but I wasn't expecting this at all..."

"So, what's the difference? I have a cock and a pussy and an asshole and a mouth. Imagine what I can do to please us.... You said you didn't like vanilla, well, this is not very vanilla."

While she talked, my hands explored her body. Her pussy was wet, drooling, and wait, the cock was her clit. Her cock drooled, so she made semen as well as grool. Her asshole was puckered and tight and right where one would expect it. Her cock wasn't huge, certainly smaller than mine. But it was a cock. And it was attached to someone I WANTED. I figured no one would probably find out, so long as I stayed quiet about it, so I did what came naturally.

I slid her cock into my mouth and treated it as if it were my own. She drooled precum into my mouth and moaned, she arched her back and played with her tits while she watched me suck her cock.

I worked it for all I knew how. but her pussy was RIGHT there and it smelled SO DAMNED GOOD. When I slid two fingers into her, she started...

"That's it, now you're getting the idea. Use me. I'm yours now, use my holes. Make me cum and I'm yours forever.... uh, ohhh fuuuuuccckkkk yes.... I'm not going to tell you what to do this time. You have to figure it out... But please, oooooooo ppppppplllllleeeeeaaaaassssseeeeeeeee make me cum..."

Her pussy was making enough drool that her crotch was puddling. Her cock was hard and I pulled off it and attacked her pussy. I had two fingers in her and found her gspot, i fingered her as I licked her labia... she was breathing hard, coaxing me on with her dirty talk, so I knew it was time. I sucked her cock into my mouth and slurped on it.... it took about 10 more seconds of fingering her g-spot and sucking her clit/cock before she exploded. Her pussy pulsed and creamed and a gushing rush of fluids coated my hand and wrist, simultaneously and surprising she filled my mouth with semen in three long shots. No cum, since she had no balls, but a pulsing orgasm of semen filled my mouth...

"Oh you fucker." She moaned. "No one - woman, or man, has ever been able to make me cum like that. I'm yours forever. You can use me for whatever you want, however you want whenever you want, so long as you make me cum like that routinely.... Now, I see you're hard again, are you going to fuck me with that big cock and mark me as yours?"