Ann's Surprise Ch. 01

Ann's Party

"So its Saturday, Date night, did you get all of the details worked out?" Ann asked excitedly.

"Do you want to know the details or just go with the flow?" Jack could tell she was excited by the thought of what might happen.

"I guess it will be a surprise date night" Ann giggled.

"Just remember this is all about you and you control the situation. Stop go, don't, it's up to you. But I get a say in it too, I can stop it if I don't like it and nobody gets mad or upset." Jack said as he held up his hand to shake on it.

"Deal"

"Deal" Jack said as they shook "And now on to the surprise, lean your seat back and rest because it will take a couple of hours to get there."

It didn't take long and Ann fell asleep in the passenger side of his sedan, one that he liked because of the room, and he was glad she fell asleep because she needed the rest, she worked long hours in the law office. It also gave him time to think about how their relationship was going. Because of the long hours she didn't have the energy to help keep it going and exciting. But one day Ann came home from the beauty shop after getting her hair done and said that a friend of one of the customers had a friend that took her husband to a local parking spot and stripped down while they were making out with each other. Before they knew it there was a crowd of men watching, so then she decided to put on a good show and she even let a couple of them touch her. She said it really spiced up their marriage. After talking it over they both decided to give it a try, both of them thought that it might spice up their marriage.

Jack pulled off the highway at a motel that had separate little cabins with an old gas station out front that was converted into an office. Right past the entrance to the motel was a barbecue restaurant that boasted the best barbecue in town. He turned in and parked in front of cabin number five.

"Oh, sorry I fell asleep, where are we?" Ann asked sleepily.

"You told me to keep it a secret, so I will. That way if you get mad at me I can leave you here so you won't know how to get home." Jack laughed. "No really I rented a cabin so that if you get real horny we won't have so far to drive to finish the night. I packed the cloths that I want you to wear, along with a brand new toy! Lots of new things for this date, but first let's get something to eat before you get ready."

"Ok" Ann exclaimed "but after this I am in control"

Ann went in to shower while Jack went out and moved things around in the car for what he said was Ann's party. When she came out of the shower on the motel bed were the clothes that Jack wanted her to wear. Ann bent down and picked up the blouse, if you could call it that. It was a shear chiffon crop top, no buttons or zippers just a couple of ties to hold it together. The skirt was a little thicker so you couldn't see thru it as easy, but if you looked you could see through it, it only wrapped around and fastened with a tie at the waist. Ann was shaking because she was very nervous, but yet very excited. There were no panties, no nylons, no bra, and just two very small pieces of cloth. She put the skirt on and it was just long enough to cover the cheeks of her well rounded ass. She didn't think of herself as large breasted, but she loved showing off her deep cleavage with sexy tops. When she put the crop top on it hung off her nipples causing the bottom to flair far from her firm stomach, the top only hung half way down her stomach, so not only was the top thin enough to see her dark areoles but also you could see her hard nipples as if she didn't have any thing on. She was known to wear the smallest bikini she could but this was more like a night gown than clothes you would wear out in public.

"Good thing it's warm or I'd freeze in this outfit!" Ann sat in the passenger seat of the car looking down at herself while Jack drove back onto the highway. Jack had explained that she needed to wear this outfit for what he had planned, knowing full well that Ann was a bit of an exhibitionist and she was all for it. She felt so exposed because the slit wouldn't stay closed as she rode in the car, her milky thighs open and her freshly shaved pussy out in the open, her firm breast jiggling with each bump. As Jack drove he handed Ann a package saying "Here are the rest of the toys you'll need for tonight"

Ann took the package and opened it pulling out a blindfold, one like people wear to block the light while they slept. "And what is this for?"

"You said you didn't want to see who it was didn't you? But don't put it on yet, I'll let you know when, and I am sure you know what to do with the other."

Ann blushed as she pulled out a dildo that looked almost like a man's real dick or at least what all men wanted to look like, made of a soft silicone material it could have been real, it even had a pair of real like balls on the base that was flat, her pussy started to get moist just holding it. The tip looked so much like the head of Jacks dick but larger there were veins on the side, this could be real. As she held it up she gave the head a kiss and teasingly said. "Is this my new boy friend? Oh my, I'm not sure it will fit, so big."

"Did you notice on the bottom you can turn the switch and it will vibrate?"

Ann examined it and found the switch, jumping slightly when she turned it on. She giggled and said "Oh shit, this is going to feel so good," as she took the dildo and parted her pussy lips, slowly rubbing her clit, "this will make a fine show."

"Ok we are getting close, are you sure you want to do this? Remember this is your show, so you take control, OK?" Jack asked as they pulled into the rest stop on the highway at mile maker 238.

"I'm sure. I'll show you I'm not chicken!" Ann answered as she put the blindfold on, lowering the seat back so she was laying back. She reached up and untied both ties holding her top together allowing it to fall free and expose her firm tits, than she pulled the skirt the rest of the way open and started rubbing her slit with her new toy. Ann could feel the car turn and could make out that Jack was backing into a parking spot.

"This should be a nice spot, you don't have to say anything except stop, and I'll be telling a story so no need to correct it, and remember its all bullshit." Jack explained watching hungrily as Ann played. He could see the glistening on the toy as she was getting wet with her cum but she was careful to only put the tip in.

After five minutes or so Ann heard Jack call out to someone, she couldn't tell who it was because the blindfold blocked everything out. "Hey buddy, want to see something nice?"

There were footsteps and then she heard from Jack's side "I'm an Uber driver and I picked up this beauty and they told me she was hypnotized. Not sure what they told her but all she did was open up and start playing with herself when I picked her up."

"Wow, nice, I love the show?" answered the stranger.

Since Jack had put the window in the halfway open position, Ann was able to hear him walk over to it, so with her free hand she started rubbing and pinching her nipples so they would get hard and stand up for him to see. She could hear his breathing quicken from her window, she opened her thighs and slipped her new toy between her wet lips, pushing the head in and because it was so big it took more pressure than she thought it should but as it slipped between her pussy lips she let out a small moan.

"Beautiful, you are one lucky dude to have picked up this fare, what are you going to do with her man?" he asked.

"Not sure but I hope the spell doesn't wear off soon, I'm enjoying the show." Jacks answered "someone is playing a joke and when she wakes up she's going to be pissed?"

Ann opened wider yet and rubbed harder letting it vibrate. She could sense, that the strangers head was at the window as he said "So beautiful, do you think she would mind if it touched her boobs?"

"I don't know, might snap her out of it, I didn't want to touch because I was afraid to wake her. You know what a great show." Jack tried to explain but didn't move from the driver's seat.

Jack pushed the button and rolled the window all the way down so the stranger could put his arm into the car and started stroking and gently squeezing Ann's breast, spending a lot of time caressing her hard nipples and running his fingers around her large areole, her breast fit nicely in his large hand as he cupped first one than the other.

Ann couldn't see the stranger not just because of the blindfold but because she had her eyes closed tight. She couldn't believe what she was doing. He said all she had to do was say stop and her lips started to open to scream but the only sound that came out was a moan because just then her breast were being squeezed and kneaded and her nipples were as hard as rock, begging to be pinched. She couldn't help herself because it felt like a bolt of lightening shooting through her body, tingling and ending at the end of her clit. Ann had forgotten all about her new toy resting in between her wet pussy lips. The stranger leaned into the car and put his hand on her tit again this time he was getting a little rougher. He was squeezing and slapping her tits, pinching her hard nipples making them harder, they were begging to be pinched, and he did, rolling her nipple between his thumb and finger, just hard enough to feel good but not hurt. She still didn't scream because it felt so exciting, and she couldn't believe it but she felt her pussy juice running down the crack of her ass. This was so not like her, with out realizing in her excitement she pushed her new toy a little deeper

Ann's head was spinning, she couldn't believe how nasty and exciting this felt. Ann wondered what Jack was doing, was he stroking his cock? Oh god she wanted to open her eyes and see what he was doing. She could feel the strangers hand leave her breast and now it was lightly brushing her stomach. Then he was stroking the inside of her thigh, she opened wide as he made his way up to her dripping pussy where her new toy was stuck between her swollen lips. The stranger slid his fingers past the toy and parted her lips, ever so lightly stroking her clit. Again Ann wanted to scream stop but instead she took advantage of the movement and pushed on her toy sliding it in a couple of inches, again she let out another soft moan loud enough to be heard. He kept fingering her clit making small circles, she raised her hips to show him she wanted more. He took her new toy into his hand so Ann took both of her hands away and caressed her tits making sure to pinch both nipples, spreading her legs as wide as she could so she could accept what was to come. With that he pushed the toy in and her hips came up to accept the thrust. He pulled it out and she pulled back, the next time he pushed harder and Ann rose up higher. Her new friend was now buried and Ann could feel the stranger's fingers around its shaft so that they were in the folds of her pussy. Oh shit, how many times will I let him do this, it felt so good, and she was so full. He pulled it back again just enough so that the toy was still in her, Ann pulled back pulling the toy out of her dripping wet pussy so that just the very tip of the toy was between her lips. After what seemed a minute but was only a mille second the stranger started to push the toy back in and Ann bucked up to meet the thrust, burying the toy and the stranger's fingers deep in her pussy. He let it rest deep inside of her then pulled it back a little only to shove it back in harder and deeper. While it was buried he tried sliding his fingers along its shaft into her pussy, and he manage to slip some of them in, instead of pulling it back out he push it in and rotated it deep inside of her. Oh my god, it hurt but felt so good Ann thought as pure pleasure swept her body making her shiver all over with pleasure, she had such a large orgasm that her cum ran from her pussy covering his fingers but it scared her really scared her.

Ann shook her head and yelled in a panic, "What the fuck! Stop! Stop right now"

The stranger jumped back jerking both of his hands back, hitting the back of his head on the way.

"Oh shit. Just go, run, I'll deal with her!" Jack yelled as he reached over to start the car.

Jack put the car in drive and pulled away as the stranger ran to the rest rooms. When Ann felt the car accelerate out of the parking lot she pulled off the blindfold and sat up looking over at Jack. First checking out his crotch then looking at his face, trying to read what was on it. He was checking traffic but glanced over at her, seeing her lying next to him, beautiful breast bouncing with the bumps and her new boy friend just barely sticking out of her pussy, covered in a puddle of cum. He turned back just as Ann's hand started to find his cock that was still hanging out of his pants and hard.

"I see I wasn't the only one enjoying myself" Ann said as she stroked his shaft. After a couple of quick strokes she leaned back in her seat that was more upright now and grabbed her new friend and began riding it with enjoyment, surprised at how deep it was while they drove in the car. She keep it up all the way to the motel, moaning and thrashing until the car stopped and she let loose with a loud climax.

"Wow I hope your not wore out by all of that excitement." Jack said as he reached over to take over and started to rub her clit while her new toy was still buried deep inside her. " Damn it's hard to hold on to it now that you have it soaked in cum"

"There's not a chance of that, I'm so horny, only your cock will satisfy me now." She said as she reached for his cock. "Now do you believe I'm not a chicken? Just wish I would have opened my eyes and watch my new friend playing with my tits, and I would have loved to have seen your face when his hand was in my pussy. What were you doing?"

"Well for you information I had the dash cam on so you can watch yourself when we get inside, and I think it caught me." Jack answered. "I mean if you really want to watch yourself chicken out"

"What! I didn't chicken out and you'll see if it's on the camera, I let a stranger maul my tits and he walked away with pussy juice on his hand." She angrily answered as she got up pulling her toy out. It made a popping noise which made both of them look at her crotch and then at each other, seconds later laughing hysterically.

"I couldn't believe you actually went through with it and let some passerby play with you. And I know you were excited because I could see how wet everything got. Wasn't real sure what I was going to do if he pulled his dick out and wanted to fuck you. Not sure if I was ready for that, but I got so damn hot watching what he was doing to you that I almost came but you screamed and I knew I had to get him off you"

"I'll have you know he wasn't on top of me, he wasn't even in me. Well he was just barely in me I mean my pussy lips were wrapped around his finger tips and damn he sure knew how to use a dildo. No I can't believe I did that either, I can't believe I let him go that far. He went further than I was going too let anyone go. I was just going to let someone play with my tits and then yell stop and damn that new toy was so nice, it felt so real and it made me so hot it could have been his dick." Was Ann's answer, "It was so exciting, forbidden, I think that is why I let him go so far, and why I was coming the whole time. Your right in the moment I'm not sure if I could have stopped him if he opened the door and pulled me too him. I was so wet and open he could have easily fucked me. I need you to make love to me."

"Only after you cover up, I'll grab your wrap from back, there is a group of guys over by the grill and it looks like they've been drinking, don't want them to think you're for hire."

Ann reached down and grabbed the door handle and said "What! Some stranger is licking pussy juice off his fingers and you're worried about how many people will see all of me. Ha, maybe my next customer will be watching and offer enough for a fuck, hell maybe I'll give it to them for free." With that she opened the door and jumped out letting her skirt open. She closed the car door and showed Jack what her outfit really looked like in the lights of the parking lot, looking at Jack exclaiming "Maybe I should just go and say a friendly hi, you know see what comes up." Giggling like a school girl she took a couple of steps away from the car, stopped and turned to Jack so he could see all of her. Then she walked around the front of the car from her side to Jacks before he could get the door open. She made sure to shake her tits causing the thin material to dance on her belly, and you could see right through it. As Jack got out of the car she got close and rubbed up against him and said "Do you give discounts for gangbangs," after a pause she said "you know I was only kidding."

"Ok you made them look at you, I got the door, let's go"

"Ok, maybe next date night, Stud" Ann yelled over her shoulder just loud enough for Jack to hear but not the street corner "and maybe next time he won't go home with a bad case of blue balls." She put in for Jack. They went inside and made wild passionate love well into the early morning.