Play Date With Cindy

Preface and disclaimers:

I wrote the 3rd story first with no plans to write more. But I like Cindy and decided to add more. It became obvious that I needed some background. As I wrote the background it took on a life of it's own now labeled parts 1 and 2. The voice is Cindy's. I edited minimally at her request. Ok? Part three is where I come in. I wrote it in my voice. Hopefully not too confusing...

This is work is copyrighted. It is published on Literotica.com. Protections apply. I like comments on my work. Critical ones are fine as long as they are constructive. I'm not expert at this game. Unfortunately, Literotica attracts trolls who get some sort of thrill by anonymously posting unconstructive and rude comments. Sad but true. The delete function eradicates them.

Usual disclaimers apply. This is pornography. If it is illegal for you to obtain or read then please do not. Also, I elected not to add elements of safe sex. I am a fan of safe sex. Characters in my stories do not contract diseases like real people do.

Lastly, like a lot of fiction, some of this is real and some is not. Readers are encouraged to enjoy guessing what is real and what is fantasy.

3 - Play Date With Cindy

We had agreed to meet at the local restaurant/pub at noon. I was a about 15 minutes early, partly eager and partly to get a table with enough privacy. Out the window I saw Cindy drive up through the beautiful fall sunshine.

I suppose I should explain my relationship with Cindy so that what follows will make more sense.

Sometimes when I am bored I read personal ads on Craigslist and other places. Once in a great while I'll find one that seems genuine and interesting. In this case I got a response. She was witty, bubbly and flirty. She was confident. Infectious. She was looking for something discrete... I generally do not date women that are married unless the hubby knows and approves but in this case I made an exception. Our first meeting changed things a bit. For one she turned out to be a curvy, chunky hottie -- exactly the type of women that turns me on the most, standing about 5'3" with a nice round tushy and big breasts that she showed no tendency to hide under baggie clothing. She had medium length, straight brown hair and sparkly blue eyes along with a creamy Irish complexion. I was smitten to say the least.

Another change happened as we talked. I allowed that I did not generally play 'discretely' with married woman and asked her about her feelings. She explained that her husband actually encouraged her to date, as long as they agreed that things were safe and controlled. She loves her husband and had no intention of leaving him. This was just something that added spice to their life that they both seemed to enjoy. By this point she was actually blushing which made her that much cuter. She said writing personal ads that tried to explain all this had not worked out very well. So she had tried to make it simpler by not going into these details.

So I pressed her a bit. At this point I do not think she realized that her home life worked just fine for me. After chatting a while the picture began to emerge. They were both sexually playful but both a bit submissive. Nothing extreme but after several years of marriage they had discovered that he was very turned on at the fantasy of her being a willing slut for another man. When they discussed this in bed it always resulted in hot sex and strong orgasms for them both. This was often followed by hubby going down on her to clean up the mess, and share some juicy kisses. That would turn them on again and off they'd go...

By this point in the conversation she was permanently flushed. With lunch eaten it was nearly time to go. We had agreed that this was simply a casual meeting to see if we liked each other. After telling me her story, she was definitely embarrassed and turned on at the same time. I'm sure she would have agreed to fuck me senseless at that point but I decided to wait a bit and ramp up the pressure. We parted with a lingering kiss that us both boiling. And a big smile from Cindy as she realized how turned on I was by the potential of this relationship. I left her with one request. Since I knew her hubby was waiting at home, and excited, and Cindy was clearly excited, I told her to give her hubby a slutty and kinky good time and to email me this evening with the details of what she did for him.

After dinner I found an email waiting:

________________

" Nick,

Lunch with you was the hottest sex I have ever had without actually having sex! Jim was waiting in the bedroom when I got home. He was naked and hard. As I took my clothes off I told him how much you had turned me on and everything that I had told you. When I was down to my panties, my rock hard nipples telling him how excited I was, I took his hand and put it between my legs. Wet hardly described my condition. Sopping might be a better word. I nearly came as he rubbed my soaking wet panties against my open pussy.

Remembering your instructions, to be naughty and kinky, I took my panties off had Jim put them on. His rock hard cock clearly visible through the wet cotton, I laid back and told him to lick me. I came hard and fast. It was amazing. I never cum that quickly... But I kept him working. I occasionally stroked his rigid cock with my toes over the panties, but not enough to take him over the edge. After 3 or 4 more orgasms I needed a break. And I wasn't sure how long I could keep Jim from going over the edge.

His absolutely favorite fantasy way to cum, something that we don't do very often, is a combination titty fuck and blow job ending with him cumming in my mouth and all over my face. With a very horny smile I wrapped my big breasts around his cock and licked the tip each time he thrust forward, I stayed in control enough to tease him for a good ten minutes. Jim was clearly reaching the point of no return, so with one arm I pushed my breasts up to cradle his cock and balls with my warm tits and I sucked his cock deeper into my mouth. I reached around with my other hand a started to tease his anus. That sent him over. After the hours of waiting and teasing and sex he started squirting forcefully. I caught a few spurts in my mouth but most went all over my face. After his last spurt I moved up and kissed him with his cum still all over my face and tongue. His still hard cock told me exactly how much he was enjoying what I did to him.

Jim helped write this and he says thank you! Now I NEED to fuck him again. God we hope I can see you soon!

Cindy"

______________

I had to masturbate twice that night before I could sleep.

It took two weeks for us to work out a date. Same time and place but this time Cindy had clear instructions about being my willing slut for the day. Earlier in the week I sent her and her hubby out to buy a new outfit. I also told Cindy to make Jim wear a pair of her panties on the excursion and to tease him as much as possible. She wrote back that they did not even make it to the bedroom when they got home. Jim had taken her from behind on the stairs and then again after they finally made it to the bedroom. She said that she was amazed, with nothing more than a few emails and one lunch the two of them had been going at it like teenagers for a week and half. But I had still more in mind.

On Friday I sent some more instructions to the horny couple. Jim was carefully shave Cindy's legs and pussy. He was told to pamper her and make sure she knew how much he loved her. Saturday morning he was to help her dress in her new outfit and send her off on the adventure. I did not tell them to abstain from sex. I was enjoying the effect I was having on the two of them.

She was stunning when she arrived for lunch. Calf high black leather boots, black tights, a pleated denim skirt that was short, maybe mid-thigh length, and an amazing red turtleneck sweater. The sweater was a soft and a bit snug. It left nothing to the imagination. I had suggested her going braless but she was not quite ready for that in public. Given the size of her breasts I could understand. We had compromised on one kinky detail, however. She and Jim had carefully cut nipple holes in the bra. The result was that her hard nipples protruded slightly through the soft, red fabric of the sweater. The entire effect was better than I could have imagined. She exuded sex. Several of the shallow guys in the pub followed her progress across the room, confused at being turned on by a 'bigger' woman. Call them clueless.

Her hair worn loose and her slightly flushed cheeks completed an image that had me hard before she reached the table. As we kissed she made sure that I felt her breasts pushed against me. She knew her role for the next several hours was to be my wanton, kinky sex toy. To be willingly and eagerly used for my pleasure.

We were in my bedroom within an hour. As I sat on the bed she stripped for me. First, she played with her nipples through the sweater, making them stand out even more and then touched herself through her tights, all the while watching the large bulge in my jeans. When she finally pulled off her tights she paused to tease her clit. She was a sight to behold, her huge breasts flushed, her nipples rock hard. Her pussy was obviously wet as could be. She rubbed some of those juices on her lips and proceeded to kiss me. Wow.

Then she set about taking my clothes off. When I was naked she whispered that she loved my cock, telling me that it's a bit thicker and longer than Jim's. As I lay on my back Cindy proceeded to massage me with her breasts, paying lots of attention to my cock, pausing ever now and then to put her wonderful nipples into my mouth or to kiss me. This couldn't last forever. Her lush body was going to take me over the edge. I told her to sit on my cock. She wasted no time, taking me deeply. As she leaned forward rubbing her breasts against my face I told her how amazingly wet, warm and slippery she felt. She whispered that she had let Jim squirt a large load of cum deep in her pussy just before she left home. She said that it made her feel incredibly sexy and slutty knowing it was there while I was in her. As you might imagine this set me off. And my nearly uncontrollable, pulsing orgasm set her off too. After we caught our breath I sent her down to clean our three combined juices off of my cock. I was hard as a rock again within minutes.

Grabbing a firm, large dildo I rolled her over and began fucking her slowly and deeply with the toy. Teasing her clit with my fingers and kissing her brought her close to orgasm again. Before she could cum I replaced the now messy dildo with my cock and as I fucked her I slowly pushed the dildo into her mouth. Watching her suck and lap at the mixture of her own liquid and the cum from two different men brought both of us over the edge again, her heaving and trembling, her muscles clenching my cock as I spurted in her for the second time.

Warm and exhausted we kissed and fell asleep cuddled on the bed.

Awake, warm and relaxed and hour or so later, I headed down to the kitchen for a drink. A few minutes later she joined me with a naughty grin on her face. She had put her hair up in pig tails. She was wearing the sweater and the pleated skirt, and obviously nothing else. No bra. No tights or panties. Yummy.

"I'm really sorry about me behavior in class Mr. Nick" she said. "You be quiet while I decide on your punishment young lady".

Taking her by the wrist I walked her into the den watching her full breasts sway enticingly under the soft, red sweater. Sitting in the middle of the couch I told her that a spanking was in order. Pulling my sweat pants down I told her get over my lap immediately.

Cindy knew her job. She positioned herself so that her breasts, in the soft sweater, were directly over my throbbing cock. And then she carefully laid down with lots of wiggling and rubbing. Placing one hand on her back I pulled up her skirt, baring her full, round ass. "Miss Cindy! I'm shocked! You're not wearing panties and you're all wet!". "I'm sorry, sir" she responded impishly. "At lunch, Johnny and Danny and I went for a walk in the woods. I lost my panties. I'm sorry".

Spanking her firmly, I made her tell me exactly how she had sucked them both hard and let them take turns fucking her. And how she had cum each time they ejaculated in her pussy. As her ass cheeks reddened I made her confess to being a cum slut. All the while the sneaky wench was rubbing her clit and squirming around with my cock enveloped between her soft, sweater-clad breasts. And as she confessed to enjoying it when the boys had their way with her she had and enormous orgasm. Even before her orgasmic contractions ended I had her on her knees and entered her from behind. As I fucked her with hard deep strokes she just kept right on cumming. I was close but managed to stop and pull out, holding off my orgasm.

I handed her my cell phone and told her to dial Jim. I could only hear her end of the conversation. She kept saying 'yes' and 'yes I am' and 'yes I did' and 'twice, so far'. Still on her knees her arms and face on the couch, I told her to tell Jim how she was dressed and what she was role playing and what had just happened. As she was describing being spanked by the teacher, I slowly entered her again. She sucked in her breath and whispered to Jim that I was fucking her again. As she told him that she was being a very naughty slut she started to cum again. And then I was cumming. Pulling out I roled her over and squirted on her face and sweater. Before I was done she had my cock in her mouth, sucking greedily, with the cell phone still pressed to her face.

I sent her home just like that. In her skirt and sweater. The rest of her clothes in a bag. My cum still on her face and staining the soft fabric over her braless tits. Her cunt still a mess of juices, with clear instructions to take very good care of Jim and to email me with the details later.