Ann's Surprise Ch. 02

This is second in series, thank you for comments but please remember this is a story. But keep them coming.

Ann's Surprise

Jack and Ann didn't see much of each other after that wild weekend, with her working late and his work being so demanding. It wasn't until after eight the following Sunday evening that they were on the bed upstairs and they finally got the chance to talk about what happened. Jack was lazily rubbing Ann's inner thighs when he asked, "So did you have a good time Saturday night?"

Ann gave him a quick kiss and said "hold that thought, I need to do something first." She jumped out of the bed and headed to the spare bedroom. When she came back she was standing in the door way of their bedroom striking a sexy poise. Her right hand was up high on the door jam and her left was on her hip, letting Jack see that her dress, which was very short and very sheer was open exposing her waxed clean pussy. As his eyes lifted to her chest he could see everything, her tits were so fantastic, large enough to over flow from his hands, with large areoles and nipples that were very hard and sticking out. When his eyes finally got to her face she was smiling and said "I bought this hoping that you would let me have some more fun soon."

"I don't know, come closer and model it for me." Jack said because he just wanted to look at her beautiful body. She took a couple steps forward and turned around modeling her new outfit, showing Jack all of her well sculptured body. She looked like a goddess, with all of the right proportions, he knew that men looked at her with desire and he was turned on watching her enjoy herself.

"All I can say is wow! But where do you plan on wearing some thing like that?" Jack asked playfully "I mean I can't take you to a restaurant dressed like that."

"It's all the fashion this year, but most women wear something under to cover up. I could wear a nice sports bra and those bike shorts you like so much so we can go out to a nice restaurant before hand. Or I could just wear a pretty bra and panty set with a jacket over, you know something easy to slip out of before we park and have some fun."

"Your making me want to take you out right now, it's a shame it's so late." Jack said as he pulled her to the bed. "Next weekend I'm out of town and the weekend after you're out of town. Damn work keeps us from having fun!" Jack said with disappointment in his voice.

Ann wrapped her arms around him and tried to comfort him the best she could. "I know it'll be at least three weeks before I'll be able to wear this for you, but I promise I'll make it great date night. Don't worry baby it'll be ok, I'll make you happy tonight."

"I still can't believe what you did and how much it turned me on, I just hope you liked it. I mean I don't want you to do anything you don't want to do, or anything you will regret later!"

Ann playfully rubbed Jacks cock "I wouldn't have done it if I didn't want to. I did it because I want to please you and you know what I'm glad you let me do it, and I'm glad you're not jealous or mad. I think that was the wildest thing that I've ever done, you were spectacular, going on and on, until early the next morning. I couldn't count how many times I came. It was a good thing that check out time was in the afternoon that way we both got some sleep. You know I think I'm still sore. I just feel bad for him, he left with a bad case of blue balls, I wonder if he had to stop and rub one out on the way back to his car?"

"I've got a question for you, what would you have done if he opened the car door and pulled out his dick, you know he wanted to get off too. What would you have done if he decided to slip it in and drop a load? He could have done it real easy." Jack asked as his fingers slipped between her pussy lips, feeling her moisture.

"Well thank god the door was locked, but I guess when you fucked me later it would have been sloppy seconds for you. Maybe that would have made you happy, sloppy and used, full of man cum. Now that would have been nasty." she answered while she took the head of his dick into her mouth. "Of course I could have always jacked him off," she said moving her mouth away from Jacks engorged member stroking it making it harder. "Or maybe I could have done this for him." She said as she parted her plump lips and took his cock in her mouth, gently sliding up and down on it, taking it deeper and deeper in her throat until she gagged. Pulling away she said "I'll bet you'd like to have seen that."

"Damn, you know I would, but would you be finished for the night, I mean would that satisfy you, or would you want more. I know if I saw a show like that I would've finished about the same time he did."

"Hell no, but I wouldn't let him go home with blue balls again and I would have to finish with your hard cock," with that she climb on top of his fully engorged cock and made love, both of them giving in too each other bonding their love for each other. They both fell fast asleep, exhausted dreaming of things to come.

As the weeks past, the thought just wouldn't leave Jack, what would she do, every time he thought about it his cock got hard, did that mean he wanted to see Ann ride someone else. Did it mean he wanted to fuck a sloppy pussy? "I'm glad we're both free this week end. Let's set a date for Saturday night, thought we might go back to the motel, you know just to see if the guys are hanging around the lamp post again." He asked Ann on the phone.

"Sure sounds good, how much are you going to charge, did you think about gang bang discounts?" Ann answered laughing at her own joke. "No really sounds good, are you going to pick my out fit or can I pick it?

"I'll let you pick it, because I thought we might stop at that fancy restaurant at the edge of town and your new outfit would fit in very nicely. We need to find some place closer this time. I was thinking about the rest area by mile marker 185."

"Cool I like that." She answered "but can you pick me up at Gloria's house? I promised her I would spend some time with her." Gloria was Ann's best friend from grade school.

"Sure, I've got to work Saturday till two so I'll pick you up around three."

The week flew by and Jack couldn't believe that he was actually nervous to go on a date with Ann, but all of the butterflies left the minute he saw Ann walking out the door. She was waiting for him, she was drop dead gorgeous, and oh my god what a dress. Her hair was pulled up in a bun and she had so much makeup on, lots of red lip stick. The see through dress showed off her strapless very low cut push up bra, not that her tits needed any help but it did accent her already deep cleavage. What surprised him is she wore a matching colored thong. Thank god her pussy was shaved because the front of the thong just barely covered her mound. She had dark thigh high stay up nylons and high heels on that made her legs long and slender. Over it she wore a long thin red jacket that came down to just above her knees, which she closed just as she got to the car. Wow she was gorgeous she could have been a high class escort tonight.

"Hello love" she greeted him as she slipped into the front seat letting her jacket fall open so Jack could have a better look at how she dressed, "how do I look?"

"Like a picture right out of the fashion magazine" he answered as he leaned over for a kiss, "or a high classed hooker, haven't made up my mind yet."

"I've been so excited for tonight, Gloria helped me pick everything out, and I had to tell her about what we're doing. She's my best friend, ever since grade school, I'll bet you didn't know that we practiced French kissing on each other to get it just right." Ann said. "I think she was more excited about my date than I was."

As Jack made his way to the highway he laughing said "Maybe we should invite her along, I could let both of you start by putting on a little show in my rearview mirror, with both rear windows down of course."

"Not a chance, she would never go for it. Beside why would I let you see her naked." Is what Ann said but in her mind she saw how it would go and she shivered with the thought of her and Gloria naked playing with each other than watching as strangers played with them. Then she thought it would go further they were taking strange men's dicks deep in their pussies while kissing each other. She shook as she had a small and quiet orgasm at the idea.

After dinner at the restaurant they left and headed for the rest area at mile marker 185. The rest stop was known for its prostitute activity so there would be some horny perverts there. You could see most of the area from the highway but the road made a couple of turns leaving one area well hidden. Jack pulled the car in the middle of the lot where a couple of the over head lights were burnt out, leaving the interior of the car dark but enough light outside from the other lights to see what was going on.

"Be right back love, going to the toilet and to show off on the way." Ann said as she popped open the door stepping out.

"Do you want me to come along and beat them off with a stick?"

Ann took off the jacket and tossed it in the back showing off her bra and panties under the sheer dress, "no I just want to see how excited I can make them, and walk off some of my nervousness"

Jack couldn't take his eyes off her exposed ass cheeks they seemed to be calling come and get it. As she walked all of the men's eyes followed her, he even heard a couple of cat calls. It wasn't long and she came walking back. Jack noticed that she had taken off her bra and panties. Jake couldn't believe she was naked under the sheer dress with only her stockings and high heels on. Along the way a short middle aged gent stopped her and tried not to stare but asked her a question. She was flirting with him as her hand unbuttoned her top button and then the second one, Jack didn't know what was said because she was shaking her head no, but when she motioned to the car it confused Jack, so as she got back in he asked her, "what did he want, as if I didn't know"

There was a giddy laughter in her voice "yes he did. Do you know he offered me a hundred bucks if he could touch my pussy, I told him I wasn't here for that but I would be making out with my boy friend over there if he wanted to watch he was welcome too" she answered while she was unbuttoning the rest of her dress.

With that Jack leaned over grabbing the back of her neck and parted his lips to passionately kiss her, he could feel her heat rising from her. Their tongues darted back and forth in a tug of war. While the only thing he could think about was how soft and moist her mouth and lips were, Ann was busy unbuttoning his shirt and running her hands over his chest. She pulled her dress open exposing her milky white breast so she could rub them against him. Ann pulled back and took Jack's free hand and put it on her so he could cup her tits which he did circling her areole with his thumb. Jack was still cupping her lushes' globes when they unlocked their lips Ann purred "why don't you turn the dome light on so you can roll down my window and see if anyone is interested in seeing a good show."

Jack pulled back so he could reach the switch and turn it on when he looked around to his surprise and saw that there were two men standing outside Ann's window watching what they were doing. He thought that was quick, as he sat back and readjusted in the seat. Ann saw them at the same time Jack did, one was the short gent that asked to pay and the other was a taller African American, both were very handsome thought Ann, both doable but not boyfriend material. Not tonight I am not that kind of slut!

Ann looked at both of them as Jack rolled her window halfway down. Ann's hands went to her tits and cupped them just to see if they were watching. The black man had to adjust his growing dick, the short man was rubbing his, nice lets see what they do now was Ann's next thought. As she opened up her thighs, spreading her hips, she reached down with her left hand to finger the folds of her pussy. She was hoping they liked what they saw because she sure did as her fingers got sticky with her happiness.

She looked back at Jack and smiled sexily and nodded signaling him she was ready, as he rolled her window all the way down she pointed her long painted finger nail at the short man, "I'm going to call you Mat and your Will" she said finishing with the black man. She motioned to them that it was ok for them to go ahead and touch her body and they obeyed, first Mat reached in and lightly brushed her tits, gently rubbing her nipples. Will slipped his hand in and was rubbing the inside of her thigh, which made her open more. Ann felt her other tit being caressed, and when she looked it was Jack playing with it, he took her hard nipple and squeezed it between his thumb and finger. She could only roll her head and moan with ecstasy and shiver with delight, it felt so dirty to have three men groping her body and yet so exciting.

Ann knew that Jack was okay with ever she did so she reached down to take Will's hand and guild it to her dripping pussy, which he did, ever so gently opening her pussy lips and inserting his index finger into her wet slippery pussy. Stroking and flicking while he stuck it in and out her cum lubricating it over and over again. With her free hand she grabbed at Mat's cock, which was still covered by his pants. Mat took the hint and pulled his hands back so he could unzip and pull it out.

Jack took the advantage and squeezed first one than the other of Ann's nipples making them grow longer and harder after that he sat back and unzipped his pants so he could stroke himself. She reached out and found Mats member and held it while Will pull his sweat pants down exposing himself.

With that Ann said "Ok boys I am going to open the door just to get a better handle on you, doesn't mean you can take advantage, got it"

They both mumbled something but let Ann swing the door open, waiting and watching for her command. Jack saw her slid to the edge of the seat leaving her dress behind, he wasn't sure what she had in mind as she reached out and grabbed both of the men's cocks in her hands, holding them she was studying them. Both men stood there wide eyed surprised and not sure what to do.

She held Matt's in her closed fist with just the head sticking out and leaned over to kiss the head. She than looked at Will's the same way but Jack noticed that her hand was still at the head but there was enough room to put her other hand on it also. She seemed to study but didn't let on that there was such a difference as she leaned to kiss the head of his dick.

"Oh how nice these are, such nice strong hard cocks, which one will be first?" she said as she pulled on both of them, stroking and stroking as both of them got harder. "This one wins"

She let go of Will's dick and put that hand on Matt's ass while she took his head in her mouth. Jack could see Will go weak in the knees, thought he was going to pass out. She then let go of his cock and started bobbing up and down on it, but when she took it all the way, burying her face in his pubic hairs Jack could see the old man had never experience anything like that. Just then Ann pulled back and put her hand over the end of Matt's cock, just in time to catch him filling her fist with his cum. Spent and finished he turned and zipped up as he walked away.

"Now come here big boy" Ann pulled Will in. She didn't suck his cock right away Jack could see she dropped her hand to play with herself while she rubbed her beautiful tits all over with his member while she stroked it making it grow to its full length. Jack could swear that he saw her shiver, cuming on her fingers, after that her hand came up and she put her fingers in Wills mouth letting him taste her sweet cum. Ann then took his hard cock in her mouth only this time she had to keep one hand on it so it didn't go too deep while one of his hands went to the back of her head. Her head bobbed up and down slurping and making noise with each stroke, so much noise it sounded like a porn movie.

But than she did something wild she took her hand loose and put both of them on his ass and pulled him in, swallowing more and more with each stroke. When he was going deeper and deeper Ann would gag with each stroke, but she didn't seem to care. Jack couldn't believe how much cock she could swallow, but than Will tensed up and Ann pulled him in and wouldn't let go. Oh my god she let him cum deep down her throat, she gagged as he pulled out but she let him finish in her mouth, she bobbed up and down a couple more times cleaning his member for him as she said, "that was very nice, cum again anytime"

Will looked at Jack and said "If you don't take care of this lady let me know I would love to"

Ann hadn't paid any attention to where Jack was when she finished but as she stood up he was right in front of her, pushing her back into her seat. The door was open so her right leg was still out side when he climbed in with her pushing her left leg hard into the center console, she didn't mind. She lifted her hips just as Jack's member found her wet hole, and he pushed. There was no resistance because she was wet and she pushed back, they made love not sex, at least that is what Ann thought, she was hoping. Finishing a while later they dressed and drove home without talking much.