Kelly Pays Off Ch. 01

Story Info
Kelly Cass makes up for a missed date at the college.
4.9k words
4.52
11.7k
9

Part 1 of the 3 part series

Updated 06/08/2023
Created 11/21/2016
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Friday evening

Back in the summer, I had arranged to have Kelly Cass come out to the college I work for to give a lecture to new communications students during orientation. She had cancelled, sending me Crystal Egger in her place. That turned into an interesting and fun visit. In return for setting me up with Crystal, Kelly had promised that she would have a surprise for me, asking if I would be free on Labor Day weekend. Late August rolled around, and I called Kelly to see if she was still on. She said that indeed she was, and was looking forward to seeing me. I asked her about the surprise she had promised, but she was still holding out, telling me she didn't want to spoil it. We coordinated on her arrival, and I said I'd see her Friday afternoon.

Friday afternoon arrived, and I went out to the airport to meet Kelly. She came through the gate and I was immediately turned on. After almost 25 years, she knew how to get to me. She was wearing a faded denim skirt that came about mid thigh with a thin coral colored button down top that had a lot of bounce in it. The fabric made her nipples stand out, and it was obvious she was braless under it. The top was open about four buttons, far enough that she would be showing a good portion of the sides of her tits, and maybe more if she leaned forward. She must have been driving guys crazy all the way from Atlanta. A pair of wedges completed the look, accentuating her legs. She waved and smiled from the top of the stairs, and I watched as she bounced toward me, her tits shaking under her top like a couple of bowls of Jell-O. I wondered if she had panties on beneath her skirt. Behind her, to my surprise, was Kim Cunningham. Kim was also doing her best to drive the guys crazy. She was wearing jeans and a white tank. Visible through her tank was a white bra with a floral pattern. If she took a deep breath, you could almost see her nipples showing through. She took my breath away.

I kissed Kelly, then Kim. I looked at Kelly. "I guess this is my surprise."

"You knew I had to have something good for you, right??" Kelly smiled.

I looked at Kim, her blue eyes sparkling, and took her hands in mine. "This is better than I expected," I said to Kelly, still looking into Kim's eyes. I kissed her again. Kim had also been a participant in a program I do for women in media. She has a depth of experience that is unequalled, and she has also written on that particular topic. Because of this she is in great demand as a speaker, and does not come out as much. We make up for it when we do get together, and we've shared some fun times. I was glad to see her. The idea that I would have both Kelly and Kim for the weekend was making the wheels turn already.

Kim spoke, still smiling. "I'm glad I could be such a pleasant surprise for you. I think I'm going to enjoy the weekend.'

"I know I will. You two are the hottest weather gals I know. It will be a real treat having the 'Two KC's' all weekend. Let's get our stuff together and go have dinner." We agreed that would be a good idea, and off we went. I helped the girls with their carry on bags. As Kelly leaned down to slide out the handle, I got a good look into her top, enjoying the view of her free swinging right breast, its stiff nipple poking out, inviting a squeeze. I restrained myself, knowing I'd get plenty of chances to play with both of them later. We got to the car. Kim told Kelly to ride up front with me, since she knew how I loved to see her in a skirt, and probably wanted to get started on her thighs as we rode.

"You know me all too well," I teased Kim. "Kelly wears a short skirt so well it's impossible to resist."

"Not that she wants you to," said Kim, a jab at Kelly.

"At least I'm not showing everyone my tits," said Kelly, jabbing right back at Kim and her almost transparent tank top.

"I dunno; you have enough buttons on that top open that you could fall out of it at any time," Kim returned volleyed back. "But, you know what I say-if you got 'em, show 'em!!"

"Now girls..." I broke in. "Let's decide on somewhere for dinner. There are a lot of good places we can go." We stopped the banter as we settled on a restaurant, picking one close to my home that had good food and where we could have some measure of privacy as we razzed one another.

We had a nice dinner, lots of playful chatter, and lots of catching up after a busy summer for all of us. I sat with Kelly on one side of the table, with Kim across from us. That gave me the best of both worlds: I could caress Kelly's thighs while looking at Kim's big tits in her thin white tank. I took advantage of every chance I could to rub up Kelly's leg to her crotch, slipping a finger into her panties to play in her thick curls, occasionally slipping it into her pussy, which was open from the constant attention, and quite slick. Finally, we decided it was time to head to the house. Kim excused herself to go to the ladies room.

Once Kim was away from the table, Kelly looked at me and said, "Give me a kiss." I did, a short, sweet affectionate kiss. "Give me another." I kissed Kelly deeply, our tongues entwining. Kelly responded by reaching into my lap, rubbing the front of my jeans, slowly stroking my semi hard cock to full mast. The restaurant had high backs on the booths, so we were not going to create a scene. While kissing Kelly, I slipped my hand inside her shirt, finally getting to feel the hard nipples that had been making me crazy so far. Kelly giggled as I played with them, playfully slapping my hand away. "We better stop before Kim gets back." I kissed her again, and we straightened up, though I kept playing with Kelly's thighs.

Kim returned shortly, though she seemed a bit bouncier as she came across the floor. As she got closer, I could now see her nipples plainly through her top, poking through it. She came to the end of the table, and leaned forward.

"Lose your bra??" Kelly teased.

"Oh, you mean this??" said Kim, pulling it out of her back pocket and letting it hang in front of her. "I decided that if you weren't going to wear one, neither was I." Her tits were hanging right in front of me, as I was in the outside seat on the booth. I reached over and grabbed the right one, feeling its heft in my hand, and playing with the nipple. Kim stood up, then looked at her top, her nipples and areolae now quite visible. "Well, I guess the guys in here will get a show that will keep them stoked all weekend. Time to get going??"

We agreed it was, and headed for the parking lot, every guy in the place noting my two dates and their shapely, well displayed tits. We got in my car, and headed to my home. The girls were quite proud of their little show, and kidded each other about flashing guys. We arrived at my place and I helped them get their bags in, taking them back to my bedroom. Once there, we were ready to get started. Kim started unbuttoning Kelly's top, caressing her breasts as she did so, making Kelly's nipples stand up as her shirt slid off her shoulders onto the floor. She let out a long sigh as Kim leaned forward to suck on them. Kim stood up, unbuttoned the top three buttons on her jeans, revealing just a hint of her dark pubes, then pulled her tank top off, letting her massive jugs go free.

Kelly looked at Kim; I was riveted to both of them, Kelly now down to a short mini skirt and wedges, Kim in just jeans, having kicked off her sandals when we got to the bedroom. Kelly returned the favor that Kim had just given her, first playing with Kim's hanging tits, then sucking the nipples til they were like wine corks. Kelly looked at Kim's jeans, partly undone and showing off some of her bush.

"No panties??" asked Kelly.

"No panties," said Kim, looking over at me. She knows how I find it incredibly hot to watch her take her jeans down to find just Kim in them. "I like the way it feels with nothing between me and my jeans, and it's surprisingly comfortable. It works pretty well in cutoffs too, right, Tom??" Kim gave me a knowing glance. She had worn cutoffs with no panties on several occasions when we had been together in the warmer months. It always led to blowout sex. She stepped over and kissed me. "And it turns me on to know you'll be watching me take them off, my big bush spilling out of them."

"Bet you wouldn't do that in a skirt," said Kelly, baiting Kim.

"Oh, yes I would," said Kim

"Oh, yes she would!!" I echoed.

"I've done it at work, too," said Kim

"No!!" exclaimed Kelly.

"Oh, yeah," said Kim, looking at me. I laughed.

"What's so funny?? asked Kelly, her curiosity piqued.

"You want to tell her, or should I?? I asked Kim.

"I'll tell that story," said Kim. "A few years ago, Kristin Dodd and I had this friendly contest going on to see who could get Adam Berg the most distracted. It started when Kristin wore a really short skirt one Saturday night, and Adam kept getting tongue tied. I was on ahead of Kristin, and watched as Adam saw her in the studio when she got up on the chair. He couldn't put two words together on his next segment. The next time I saw Kristin, I mentioned the situation, and asked her if she wore that skirt on purpose. She said she had not, but had also noticed the effect it was having. She said she was going to wear something like it the next weekend. I told her I bet I can distract him, too. That started it. The next time I worked with him, I also wore a really short mini. Again, Adam couldn't get a segment done without flubbing it somewhere.

"Kristin and I kept at it, giving him lots of leg. Then one Saturday, he was really bad. I found out that Kristin had flashed her panties at him right before one segment, and it wrecked him. The next time we were on together, I flashed him a really skimpy, sheer pair I have. He had to see my bush not only through them, but poking out around the top and legs. Kristin upped the ante by wearing a G string. I wore crotchless; the next week she did. The week after that, I flashed him my bare pussy. Kristin had me on that one-she showed him her bare pussy the next weekend. She has the hairiest twat I have ever seen. His eyes must have popped out of his head when he saw that.

"So who won??" asked Kelly.

"I did," said Kim proudly. "The following weekend, Tom came up to help me with those remote stations we used to have to check on. We spent the weekend together. I was working with Adam on Sunday. That morning, I put on a really short mini with no panties, knowing Tom and I would be spending the day together. You know how he likes a short skirt."

"Yes, I do!!" said Kelly, slapping my ass.

"Well, I teased him all day."

"Yes, you did," I said.

"Was it worth it??"

"Absolutely!! You were hot. And the payoff was intense."

"At the end of our day, I took Tom back to TWC with me, since we had left his car there the day before. I had put my on air clothes in the back of my car on a hanger. When I went to get it, I lay back on the seat, my legs spread. I was so hot by then, my pussy was already open. I don't think he needed to be asked, but I just said 'fuck me.'" You were on me in a flash!!" Kim looked over at me, smiling.

"We screwed like it was the last thing we'd ever do," said Kim, looking at me, then back at Kelly. "He came so hard I thought he'd knock me off the seat, and he came in buckets. I'm still amazed, thinking about it, that there wasn't a steady stream of your come running down my legs all night," said Kim, looking at me. "When I got in, I sat at my desk getting ready. Adam stuck his head in the door to ask me something. While he was standing there, I leaned back in my chair, letting him look up my skirt. I opened my legs and a big white blob of Tom's sperm dripped out, with more flowing out of me right behind it. I thought he was going to have a heart attack. Adam could not get anything straight that whole night."

Kelly was open mouthed in disbelief as Kim told the story, then let out a big laugh as Kim told of Adam's response.

"Kristin had to concede to me on that one. I told her the only way to top that was to let him see you getting balled," Kim added.

"I suggested that to her," I said. "We could never manage to make it happen. The idea was to let him catch us on her desk, just as I was pulling out after giving her a big load."

Hey, whose side are you on anyway??" said Kim, acting insulted.

"Anyway," she said to Kelly, "you should try going without panties some time."

"Oh I have," said Kelly, looking at me, smiling. I nodded in agreement.

"She has," I said. "It's led to many good times over the years."

"I'd have gone without today, but my husband insisted on having sex with me this morning before I left, and I didn't want to be dripping come all over the seat on the plane. Even though he's almost 50, he still comes A LOT!!" As Kelly spoke, Kim was pulling down her jeans, slowly revealing her thick dark curls. "Wow," said Kelly watching Kim intensely, almost mesmerized by the sight of Kim's bush. "That is hot."

Kim looked intrigued. "You have a cream pie?? That's it, drop 'em." Kelly looked at Kim, then reached up under her skirt and pulled out a pair of sheer light blue panties. The crotch was wet. Kim took them, placed then to her nose and inhaled.

"Mmmm...come in your panties!! He must have given you a good load, they're pretty damp. Let me see what he did." Kelly unzipped her skirt, letting it drop to the floor. She was now standing in front of us wearing nothing but wedges, earrings, a watch, and her wedding set. Her bush was parted where her labia were open, a thick tuft of hair over the opening. Kim took Kelly's hands in hers, easing Kelly down on the bed. Kim knelt in front of Kelly's spread legs, then dove into her exposed womanhood, lapping eagerly. A minute later, Kelly let out a sigh.

"Oh yes," said Kim, coming up for air a moment. "There it is, that tasty cream pie. I'm going to have it all." Kim continued to work on Kelly, who was now breathing harder. Kim stuck her tongue inside Kelly to get as much of her husband's come as she could lick up, sending Kelly into orgasm, crying out as her colleague stayed nose deep in her spasming pussy. "Oh, that's tasty!!" said Kim. "I knew there would be a lot in there for me."

I had stripped while Kim was going down on Kelly, who was lying on the bed looking happily disheveled, her hair all over and unkempt looking. She was gorgeous. Kim turned to me. "Your turn."

I smiled and got on the bed with Kelly. She reached for my cock, already hard, and pulled me to her. "I'm so horny right now, put that stiff dick inside me." I didn't hesitate, getting in position over her, then after rubbing her clit with the head, sliding into her slowly. Kelly let out a long sigh as I filled her, finally coming to rest with my balls on her ass and the head of my dick on her cervix. "Mmmm...I love how you fill me." I started pumping slowly, making sure I got good contact with Kelly's clit on each stroke, bottoming out in her womb. It was a turn on knowing that she was not only worked up from Kim's attention, but that I'd be the second guy to come in her that day. It didn't take long til I was ready to come, but I didn't want to blow my whole load in Kelly(well I did, there's nothing more satisfying, but there would be many chances to do that over the weekend), and wanted to save some for Kim. I knew if I could pull out so just the head was inside her, I might be able to reach the point where I was stimulated enough that I would have a heavy flow of precome, but not have a full orgasm-basically edging into her pussy. Once I do this, I can usually keep going for quite a while. It makes for some long love making sessions, which my partners and I truly enjoy. Tonight, it was going to allow me to deposit my seed in two of the hottest ladies in broadcasting.

I pulled back as I felt my come starting to rise, and relaxed every muscle in my groin. This kept me from clenching my ass, which would start the unstoppable progress toward a full ejaculation. Kelly looked up as my come started to flow, slowly filling her pussy with a thick coating of semen. Her eyes got big as she realized what I was doing, then she closed them again.

"I love when you come in me like that, it's so hot." She then started to go into her own orgasm, and I could feel her pussy pulsing around me. I pulled out of her, a thick white stream still oozing from my swollen cockhead. I let it drool into her bush and on her clit, sending her into a frenzy. I held the leaking head on her clit as she thrust at me. The release pulled me back from the edge, and we watched as my cock throbbed in front of her. I slowly pushed it back into her now sloppy cunt.

"So how does it feel to have two guys come inside you in the same day??" Kelly and I always have some good love making time together when she comes to visit, but I'm the only other man she goes to bed with regularly besides her husband. Hot as she is, she is pretty faithful, unlike some of her colleagues. Thus, it was quite unusual for her to get balled and spermed by two men in one day.

"Oh, God it's so hot. I feel like such a slut, but it's so good!!"

"You'll get used to it," Kim chimed in, smiling. "There nothing more exciting that feeling that second or third load spewing into you."

I looked at Kim. "Care for sloppy seconds??"

Kim looked at Kelly's dripping twat, a thick stream of sperm now spilling out of her and rolling down her ass.

"I love sloppy seconds-and I love the taste of your come!!" Kim got up on the bed and planted her face in Kelly's leaking pussy, immediately trying to lick every drop of my semen from her. Kelly, who had come while I was drooling my come inside her, was already well on her way to another orgasm from Kim's attention. Kim's ass was facing me, allowing access to her spread labia. I got behind Kim and started licking her pussy lips and clit while she licked my come out of Kelly. She opened even more to my tongue, moaning gently as I started her toward her own orgasm. I put my tongue inside her, sucking on her clit. She broke away from Kelly long enough to tell me to make her come, she wanted to come from my tongue while she was sucking my come out of Kelly. Kelly was in her own world by now, moaning loudly, telling both of us how she was loving Kim's tongue in her pussy. She then let out a big moan as Kim brought her off.

"Yeah, Kelly, come all over my face!!" Kim exclaimed. "Wash my face with your juice, squeeze both loads of sperm out of your slutty cunt!!" That sent Kelly into overdrive, and she started thrusting her pussy into Kim's face. I licked Kim's clit as I sucked on it, sending her into an orgasm as well, her hips shaking and dancing on my tongue. "Oh God, Tom, fuck me, put your cock in my hairy cunt and fill me with your hot come like you did to Kelly."

I stood up and lined up my cock with Kim's spasming hole, teasing her clit as I got ready to plunge in. I was still leaking come from my earlier round with Kelly, and I got Kim all slick as I teased. "In me!! Put it in me!!" Kim cried out. I thrust into her, going all the way to my balls. I felt them hit her clit, and slap against her pubes. Kim's orgasm kicked up as I pounded in and out of her, slamming my nuts on her, and hitting her cervix with the head of my cock. I was already primed from dropping most of a load in Kelly, and I knew it would not be long before I was giving Kim the rest of it. I felt the urge rising in my balls, and knew it was time.

"I'm coming, Kim."

"Give it to me baby, fill me. Fill me with your hot come so Kelly can lick it out of me." I pushed deep into Kim, and felt her clutching vagina squeezing my cock. I started to come, spurt after spurt, much more than I expected, as I had just edged a sizeable part of my load in Kelly. Kim was not expecting it, and cried out as it hit her cervix. I finally quit shooting, and held my dick inside her, enjoying the feeling of her now messy cunt. As I softened, I pulled out of Kim, watching as her pussy started drooling my come. Kelly didn't waste any time, pulling Kim up and getting her into position so they could lie on the bed and get into a 69.

12