Tom Does Debbie Then Cyndee

This is part of an ongoing story over multiple Categories with common characters.

*****

"Ding!"

I woke up to a text. Kelly and Ellen had gone back to Vegas, Lori and I were hotter than ever and I was back in my own place; life was good.

Cyndee -- "We have to talk sweetie."

Oh, sweetie eh? Good news a hot woman called me sweetie, bad news it was Cyndee. Or was it really that bad? She was fun, open to everything, but a little drama filled.

"Ding!"

Cyndee -- "Can I talk to you today?"

"Ding!"

Cyndee -- "It's really important."

Oh geez, see what I mean -- drama filled. I texted her back.

Me -- "Sure. What's good for you?"

Her -- "You fucking me, but actually I can go to your place or somewhere else."

Me -- "Okay, how about Cup in Time?"

Nothing came right back to me; then...

Her -- "Sure. 11 work for you?"

Me -- "Sure. See you then."

I thought, hmmm, Cyndee at Cup in Time, fuck her in the van, come back and meet Lori there on lunch, fuck her in the van then take her back to work and fuck Dave at the office. Yeah, right! Like that could happen. Could that happen?"

"Ding!"

Oh shit, what now? Oh, Marcus!

Marcus -- "In town for the night. Got some time to get together?"

Me -- "Oh hell yeah. Let me know what works for you. I'm free after 1:30 this afternoon."

Just in case my fantasy comes through today. 

I cruised into Cup in Time a bit early and Debbie was working the register, Jason at the bar.

"Hi Tom," she said with a smile. "Doppio?"

"Yep. Hey can I buy Cyndee's drink when she comes in?" I asked.

"Sure. Just leave your card here and I'll ring up both of you at the same time then bring the card out to you," she replied.

"Sweet, you're the best," I said. "Thanks."

"For you, anything Tom," she replied. Looking around to see if anyone could hear she leaned towards and said, "Since Scott, you and I fucked; wow, every time Scott and I fuck; it's great. Thanks!"

"Oh, glad to hear that," I said. "You guys make a good couple."

"I agree," she whispered. "Any chance of just you and me getting together?"

"Really?"

"Yeah, really," she continued. "I know you and Scott get together without me and I was just thinking maybe we could."

Well I had heard Scott agree to it after we had our threesome so I replied, "I'd love to spend some quality time with you."

"Ohhh," she said. "You're sweet. Makes me want to suck your cock right now."

"Doppio for Tom!"

"Got to go Debbie," I said. She came back with "Let me know when." I'm sure I would.

Jason handed me my drink. "Been a long time," he said. "Since, you know."

He was right; it had been a long time. Cyndee kind of messed up the balance Jason and I had. Again; drama-filled. I looked at Jason, thought it over about how good it had been with him and said "Want to get a drink sometime?"

He smiled and replied, "Yeah; I do. Text me, I'm pretty open."

"Count on it," I replied.

"Hear about Cyndee?" he asked.

Oh shit. "No, but I'm sure I will. She's meeting me here in a few."

"Oh, well here she comes," Jason said as she walked into the store. "Have fun!"

I nodded and walked over to her. Debbie rang her up and handed me my card.

"That was sweet of you Tom," Cyndee said. "I sure needed that."

We walked over to a table, I sat with my back to the wall and she across from me. Just a side note -- always sit with your back against the wall; ask Wild Bill Hickok. GTS.

"So what's up babe?" I said.

"Do you know a guy named Carl?" she asked.

"Yeah, I know a Carl," I replied.

"I guess you, he and some other guy fucked Kathy and now she says she's in love," Cyndee said.

"What?!" Some "other guy"? Kathy was on the phone to Cyndee when I was fucking her; hell she even told her and she's saying some "other guy"? What is she up too?

"Yeah, I guess she and Carl are an item now and she wants him to move into my place," she said as she took a drink.

Fuck. Carl and his girlfriend had broken up recently so maybe Kathy was Ms. Right Now for him. Well that's kind of good for him. Wonder how the three of them will get along. Cyndee answered that question for me.

"Well the bitch wants me out of my place as soon as possible." she said with disgust. "I know I should have signed that fucking lease."

"Well if you're not on the lease, that's great," I replied. "You can just walk away."

"Yeah, fucking great," she said sarcastically, "But I'm short on cash and my cards are maxed out."

Uh oh.

"So I was thinking; since we are such good friends..."

Oh no. "Maybe I could live with you for a couple of months," she said. "I could sleep on the coach if you wanted me to. Or something else," she said with a smile.

Oh fuck! So much went through my mind -- what would Lori say? I like my privacy. Marcus and the others love coming over to my place to fuck and suck? She's going to want to do everyone when they come over. No more quality guy on guy or guy on guy on guy etc. time. I took a deep breath.

"I promise I won't get in your way," she said, continuing with "I can cook dinner for you (she can't cook) and clean the place (she doesn't even know how to use a vacuum cleaner) and whatever else you need or want (she does have a nice pussy)." She smiled and whispered, "And you know I'll fuck you every day if you want it."

Well at least that was true, but I was getting plenty of action already and not with added drama.

Oh fuck!! Lori just came in. She saw me and waved, I waved back. Cyndee turned around and looked at Lori, smiled and waved too.

"You going out with that lady?" Cyndee asked.

WTF? She didn't say cunt, bitch, or anything along those lines; just "you going out with that lady?" Oh shit. She really does need a place to stay.

"Yeah, we are," I replied. "It's early."

"She's pretty," Cyndee replied.

Oh, she really, really needs a place to stay. Lori walked over to us and said, "Hi Tom, good seeing you. And hi," she hesitated, "Cyndee?"

Cyndee smiled and stood up, saying "Yes, right Cyndee." Looking at me she said "Why don't you two have fun, I have to be going. Tom, think about what I said and we can talk about it later. Take care you two."

Cyndee waved and went up to Jason; he put the rest of her drink in a to-go cup, then left.

"Geez baby," Lori said as she sat down, "It's so good seeing you."

"You too sweetheart," I replied, and it was good; really good.

"So anything new?" she asked. Obviously she heard what Cyndee said on the way out and she probably knew that Cyndee and I had history.

"Cyndee's looking for a place to stay; her roomie has a guy moving in and wants her out."

"That sucks," she said. "You know her roommate?"

"Yeah," replied nonchalantly. Lori didn't fall for it.

"Oh, so you fucked her too," she said matter of factly. "Is there anybody you haven't fucked?"

"What?"

"Nah, just messing with you babe, I like that there are other people attracted to you," she said smiling. "Can I still have you anytime, anyplace?"

Oh yes! She wants to fuck me in the van!

"Of course."

"Good to know lover. If it ever changes let me know okay?" she said. "So, what are you going to do?"

"About what?"

"Cyndee. You going to help her?"

I shook my head, "No, she wants to move in with me, but I don't have the room for one thing or the desire for the other."

"She wants to fuck you, doesn't she," she asked.

"She always wants to fuck me," I said. "Or the guy behind the bar, or her current roommate, or fuck; everyone."

Lori looked at Jason and asked "She fucked him?"

"Oh, yeah, many times, even lived with him for a while."

"Wasn't she your girlfriend?"

"Oh yeah, she was at one time. Then we had a couple of three ways and she became Jason's girlfriend, then she dumped him for Kathy, her roomie."

"You guys had a three way?" Lori asked. "This is getting interesting. Tell me more."

What the fuck, I went on, "Oh yeah. Two guys and her, me, her roomie and her, then there was the time in Vegas."

"Vegas?" she asked.

"Yeah, me Edwin and Alexa," I said.

"You know Edwin and Alexa?" she asked.

Oh shit, oh shit, oh shit! Why was this girl so easy to talk too?

"Did I say Edwin?"

"Yeah, and you said Alexa," she replied. Smiling she said "I know them."

Oh fuck! Vegas, Lori knew Kelly, fucked Kelly, whatever and Edwin knew Kelly and so did Alexa. Oh crap.

Lori reached over and grabbed my hand and said "Tom, its okay babe. I know you've fucked a lot of guys, girls, and trannies; so have I. And we're going to fuck a lot more. It's cool babe; what do you say all the time? Grownups doing grownup things."

"You're the best Lori," I said sincerely.

"So are you," she replied. "So Cyndee; Cyndee right? She's fucked Alexa? How'd she like it?"

I laughed, "She loved it."

Lori nodded her head. "You know, I miss not having Ellen around all the time."

"Yeah, she's pretty nice."

"Enthusiastic fuck too," Lori said. "Sounds like Cyndee is one too."

Okay, where you going girl? "So?"

"So, I do have that extra bedroom, and I wouldn't charge her much rent," she said. Then locking eyes she added "I'm sure we could work out an agreement of some sort."

I was speechless.

"You okay babe?" she asked.

"Huh? Oh yeah, yeah," I lied.

"What do you think?" she asked.

"Well, she can't cook," I said. What the fuck was that all about?

"I have you for that," she said with a laugh. "Would you be okay with Cyndee living with me?"

"That's up to you," I said. "I trust your judgment."

"Cool, get in touch with her and make arrangements for her and I to meet and discuss it," she said. "Just her and I."

Damn, that would be fun to see. I took my phone out and texted a message.

"Ding!"

Lori's phone went off. It was a group text.

Me -- Cyndee, this is Lori. She may be able to help you out with your living situation.

Cyndee -- "Really? Hi Lori, we have to talk."

I almost wet myself reading that one.

Lori -- "Yes we do. Are you free tonight?"

Cyndee -- "Yes."

Lori -- "K. I'll text you my address and a time that might work for both of us."

Cyndee -- "Great, looking forward to it. Thank you Tom!"

This is crazy shit I thought. That and I realized I wasn't going to fuck Lori in my van. Not Cyndee, not Lori; strike two!

Lori got up and said "I have to go babe, Dave's running behind at work (strike three!). I'll let you know what happens with Cyndee."

"Wait!" I said. "What happens if she finds out that you're, you know, special?"

Lori laughed, "If? No babe; that would be when she finds out."

She gave me a sweet kiss on the cheek and took off.

After Lori left, Debbie came over to the table. "Hey, I'm off in fifteen minutes. You thought about what I said?"

Actually I hadn't, but what the fuck, "Sure have. Want to come back to my place?"

She smiled, "Hell yeah. Scott is replacing me so when he gets here I'll take the car and come see you. Sound good?"

"Oh yeah babe, sounds really good," I replied sincerely with a smile. I texted her my address, finished my doppio and headed out.

Debbie was at my place in thirty minutes, we were naked in thirty two.

I had already pulled a bottle of lube, Mr. Pink and the big black dildo, not the smaller glass one; she saw it, nodded her head, smiled and said "Nice."

I pulled her back on top of me on my bed; we kissed passionately out tongues moving from mouth to mouth, my cock really hard. She pulled away and slid quickly down to my cock, grabbed it and took it into her mouth. Looking up at me she said "I been thinking about this since the last time we did it." She wrapped her mouth around the head of my cock and began to massage my balls. I rubbed my hard nipples; she went down my cock really slow, wet and hot. For a brief second I wondered what Scott would say if he knew. Then remembered Debbie had spelled it out pretty clear to him. If he was going to suck and fuck me on his own, she could suck and fuck me as well. Sounds like a win, win to me; okay, win, win, win.

She had taken my cock in her hot mouth and was going back up, nice and slow, hell; she was even making yummy sounds. I like an enthusiastic cock sucker, who doesn't?

I grabbed her shoulders as she went up and down my cock, picking up speed. No way girl; you're not going to make me cum right out of the chute. I've got plans for you. I pulled her up from my cock and slid down between her legs. She tried to straddle my waist, but that's not what I wanted. I slid up farther, her pussy now on my mouth. I wrapped my arms around her thighs, held them together locking her crotch right on my mouth. She couldn't go anywhere and I started to lick her clit.

"Ohhh," she said softly. My hot wet tongue licked in circles around her moist pussy, reaching her clit. I stayed on it for a while, licking and sucking, she moaned and tried to move off of me, but I held her in place. Damn, the girl was wet! I slid my hard tongue up inside her pussy, slipping it in and out, holding close. I did that then changed it up to her clit, and then back to her slit, she was wiggling in pleasure.

After about five minutes I let go and flipped her onto her back. I reached over to the night stand, grabbed the dildo and slipped it inside her. "Oh fuck!" she said. I pushed it all the way in, bottoming out inside her moist pussy. "Oh yeah, baby, oh yeah," she said.

I grabbed Mr. Pink, turned it on and gave it to her. She knew what to do and was buzzing her clit, her pussy clamping down on the dildo. I moved to my knees, went to the side of her head and she grabbed my cock with her other hand, bringing it into her mouth. As she started to suck my cock and buzz her clit I started to talk.

"Oh Debbie, that's it," I said as I slowly slid my cock in and out of her mouth. "You like sucking me while your pussy's packed?" She just made yummy sounds.

"It's hot babe, seeing a big black dick in you while you suck me. That black cock looks good with your white skin." More yummy sounds and she was breathing heavier.

"Oooo, any time you want a real big black cock to fuck you, let me know; I have friends," I said. That took her over the edge.

Debbie started to cum, really, really hard. She clamped down on my cock, not being able to suck it, but not wanting to pull it out. She bounced up and down slightly, waves of pleasure rippling through her body. "Oh fuck!" she shouted, pulling my cock from her mouth and tossing Mr. Pink away. I reached over and put it back in her hand saying "You might want this sweetie." I pulled out the dildo, got off the bed and stood at the edge. I reached down and pulled her by the ankles to the edge and shoved my cock inside her super wet pussy. She moaned as I went balls deep, Mr. Pink back on her clit.

As I started to fuck her, in and out, deep and slow I said "Baby, you are so wet! If I didn't know any better I'd swear someone else had already cum in you."

She looked at me and said "What if they had?"

"I'd have gone down on you and licked you clean before fucking you now," I picked up speed, ball banging speed now.

She began to breathe fast and replied "I'll hold...you to it from... now on. Oh fuck!"

Holy shit! She was cumming again! Her pussy grabbed my cock tight and I lost it. Bam! I shot my first of three huge gobs of cum into her pussy as she kept cumming. After many more pumps, dry firing all the way, I pulled out and looked down at her.

"Bring me some cum Tom," she said.

I dropped to my knees and started to lick her cum drenched pussy, my cum already oozing out. I brought it up to her mouth, she pulled my head close and I slipped it into her mouth. Our tongues fought over it, both of us trying to swallow as much as we could. I went down and back up to her two more times, after the third one I had licked her clean. She pulled me close and held me in her arms.

"You are one crazy good fuck," she said.

"So are you Debbie, so are you," I replied.

"Ding!"

"That yours or mine?" I asked.

"I think it's yours," she said.

I grabbed my phone and it was a text; from Cyndee.

Cyndee -- "Meeting Lori at 6 at her place. Can I talk to you before we get together?" Seriously?

Debbie began putting her clothes on and said, "I'm sorry Tom, but I have to get going."

"That's fine," I replied.

"Geez, that was a good fuck," she continued as she jumped in place pulling up her jeans. "I can see why Scott loves being with you."

"He's a good guy," I said.

"Oh yeah he is," she said as she finished getting dressed. "I'm lucky. In the past the guys and girls I went out with were too possessive. They didn't like me seeing other people. But Scott's good with it."

Ahh, I thought. Guys and girls she went out with, other people. Okay, I see where she's coming from. Debbie leaned in and gave me a kiss, a sweet one on the cheek, a "between friends" kind of kiss.

"Thanks again Tom and hope I can see you soon," she said. I walked her to the door. "I'd like that," I said it and I meant it. Debbie was a sweet girl; hell of a fuck too, but a sweet girl. As she stepped out the door she turned and asked "Do you really have a friend with a black cock?"

"Oh yeah," I said. "Why?" I asked, knowing the answer.

"Well, you thinking me sucking your cock with a black cock in me was hot, and I'd like to make that happen for you."

"I'll keep that in mind, I'd like that to happen too," I said with a smile. "And knowing you, I'm sure Marcus would like it too."

"Marcus," she said. "I like that name. Take care," and off she went.

I looked at the text and wasn't sure what to do. Fuck it, I sent Cyndee a reply.

Me -- "You bet. Now work for you?"

Cyndee -- "Be there in ten."

Oh shit! I went into the bedroom, tidied up and put the "toyz" away. No time to shower, I threw on some loose fitting jeans and a T-Shirt. Fuck the shoes.

"Ding!"

Fuck, fuck, fuck!

Marcus -- "Hey man, what's good for you after 5?"

Me -- "5 o'clock on is fine."

Him -- "What kind of pizza you like?"

Me -- "Anything with meat."

Him -- "That figures, LOL. 6 work for you?"

Me -- "Great. See you then."

Knock, knock, knock. I went to the door, it was Cyndee. I let her in she went to the kitchen and asked "Okay if I have some wine?"

I followed her in and said "Of course babe."

She looked at me and smiled, "I like it when you call me babe."

I pulled out some glasses and she grabbed a bottle. It was already open and she filled the glasses up. We clanked glasses "Cheers! Then we sat down at the dinner table.

"So what's up?" I asked.

"How well do you know Lori?" she asked.

"Pretty well," I replied.

"I mean besides fucking her; you do fuck her right? I mean I would, she's really good looking, something different about her too," she rambled on.

"I trust her completely, we've went through some interesting times together," I said as I took a sip of wine.

"Well, I thought I could trust Kathy and look what that got me," Cyndee said.

"You know, the heart wants what the heart wants," I replied.

"Oh fuck that," she said. "The cunt just wants a man and constant fucking."

Wow, that was harsh. "What about you?" I asked.

Cyndee looked at me and said matter of factly, "I'm happy with who I am. I don't need a man to "complete" me; but I do like the constant fucking." She finished her wine, quite quickly as a matter of fact, and continued. "I appreciate your help and if you trust Lori, I'll trust her too."

"Good, glad I could help," I said.

"Thanks, now want to fuck?" she asked.

"Let's go!" I grabbed her hand and led her into the bedroom. She went to the nightstand and pulled out the lube, Mr. Pink -- gave it a quick turn on to check the batteries -- and the big black dildo. She stuck in in her mouth, licked it and asked "Lori?"

I laughed, "No, not Lori."