Their First Play Date

"I don't know what to say. This was not what I expected. So far you and I are the only one's who have fucked." He said, looking at Jan.

"You can see why I wanted that? I couldn't have waited to fuck her and both of you if I'd tried this first!"

They let Anna rest for twenty minutes. When they uncovered her she opened her eyes and Jim could see she had been crying. Jan asked, "Slut, why were you crying?"

"I've never felt anything that powerful, that overwhelming before, Mistress. I cannot describe it. I still feel it. Thank you, all of you."

"You also have made a mess. There is a puddle on my nice massage table. I think since it came out of you, you should lick and suck it off the table. Don't you?"

"Yes, Mistress." She was a bit wobbly when she stood but by holding on she got the job done. Pete said he was getting hungry. Jan asked the men to watch Anna and she went inside. When she returned she had shorts and t-shirts for both men and a t-shirt for Anna.

"Please, get dressed. We'll go get lunch." Anna looked at the t-shirt and realized it would barely cover her and was thin enough that her red bra and stockings would show. She looked at Jan who was in tiny shorts and a bikini top.

"Put it on or go without, but you are going." Jan said. Anna pulled the shirt on and stood beside the massage table. All of us were aware that if she bent at all her bare ass would be exposed. The stockings were completely exposed. They walked to Jim's SUV and Jim drove, with Jan up front, Pete and Anna in the back. Pete had picked the lipstick vibe up as they walked to the SUV.

"Spread your legs, slut." Pete said. Jim noticed that Jan spread her legs too.

At the shopping center Jan had Jim pull in and park by the Subway. She handed Anna a piece of paper and two twenty dollar bills.

"Get the sandwiches and chips and bring them to us. Then go back for the drinks."

Anna gulped and said, "Yes, Mistress."

As she opened her door Pete got out as well and slid the lipstick vibe into Anna's pussy. He did not turn it on. "Keep it inside you. Now, get our lunch!"

"Yes, Master." Anna walked as fast as she dared. She was glad there was no one in the Subway except the three employees. She handed the paper to the woman behind the counter and all three employees went to work. Twice they sent Anna back to Mistress Jan to ask about things. "Did she want the sandwiches toasted?" "Did she want the regular mustard or the spicy?" Jim, Pete and Jan noticed she was holding the vibe in with pussy power and on the second trip back to the store she used her left hand to push it farther back up inside her pussy.

She paid for the sandwiches chips and drinks and brought the sandwiches and chips to the SUV. The more she walked the harder it was to walk and hold the vibe inside. As she turned to go back for the drinks Mistress Jan said, "Pull it out! Now!"

Anna's eyes flared and she looked around as she reached in and got the red vibe. She held it towards Mistress Jan and heard, "Turn it on and put it back inside. Do not spill our drinks."

She pushed it deep up inside her pussy and walked quickly into the sandwich shop. They had put all four drinks in a carrier. She picked it up and thanked the three employees for their service. She hurried back to the SUV. Jan took the drinks. Anna said, "Oh God! Thank you Mistress. May I get in please?"

"Yes. Take the vibe out, suck it clean as you get in." Mistress Jan said.

She pulled it out as a car drove by. They watched and almost had an accident. She stuck the wet vibe in her mouth and ran around the SUV to get in. As soon as she was seated she thanked all three people in the SUV. She thanked Jan for teaching her. She thanked Pete for being patient with her. She thanked her husband Jim for loving her.

Pete started the vehicle and drove home. Mistress Jan turned and asked, "Anna did you cum?"

"No Mistress! I was so close but you told me not to cum."

"What do you think would have happened if you had cum?"

"I would have dropped the drinks, Mistress and I would be punished."

Jan asked, "Master Jim, what would have been the punishment?"

He thought and then said, "She made a mess. She would need to clean it up. Paper towels or napkins, on her knees in the parking lot until it was cleaned up and the paper goods thrown away."

"Very good, Master Jim. Now aren't you doubly glad you didn't spill?"

"Yes Mistress." Anna said. She wanted to glare at Jim, but dared not.

Pete offered, "For me, she would have had a straw and sucked it all up. All four drinks."

Anna moaned, but said nothing. When Pete parked in the driveway Anna carried the sandwiches, chips and drinks to the picnic table. She unwrapped all four sandwiches and the bags of chips. She put the straws into the drinks. Pete, Jan and Jim sat down. Anna stood.

"Anna, feed Master Jim a bite of sandwich. Use a knife and cut off a bite sized piece and feed it to him."

"Yes, Mistress. She cut a small sliver off the end of Jim's sandwich and fed it to him. Then she looked at Mistress Jan.

"You didn't thank him for letting you feed him? Are you ungrateful to be allowed to serve your Master?"

"I'm sorry Mistress, Thank you Master Jim for allowing me to feed you."

"Are you going to ignore Master Pete and me? Aren't we going to be served?"

"I'm sorry Mistress! I didn't know." She quickly moved to Mistress Jan's sandwich and cut off a piece and lifted it to Mistress Jan's face. "Do you think I have a hippo's mouth?" Jan screamed, "That piece is huge! Cut it in half!"

Anna was flustered and followed instructions. Before she picked up the smaller piece she asked, "Is this the size you want Mistress?"

"Yes!" Anna picked it up and slid it into Mistress Jan's mouth. She quickly moved to Pete and held the knife against his sandwich, but didn't cut. "Please Master, teach me how much sandwich you want in each bite."

His hand covered hers and he moved the knife blade where he wanted her to cut. She did, thanking him for teaching her. She fed him and thanked him for allowing her to serve. For twenty minutes she ran from person to person, cutting and serving. The thanks were given with every bite, of sandwich, every chip and she held the cups for each person to drink.

When she fed Master Jim's last bite to him he slid a bigger vibe into her pussy. It wanted to slide right back out. She held it in with her left hand as she thanked her husband Master. She moved to Mistress Jan and fed her the last bite of her sandwich. Jan slid the lipstick vibe into Anna's ass. She thanked Mistress Jan for allowing her to serve and for putting the vibe in her ass.

"Remember, Pet, you are not to cum." Mistress Jan reminded.

She fed Pete the rest of his sandwich. She thanked him for allowing her to serve.

Her sandwich had not been touched, her chips bag was unopened and her drink sat full in a puddle of condensation.

Mistress Jan said, "Master Jim, please turn on both vibes. Anna you have until you cum to enjoy your lunch. Before you can eat you need to hydrate. Drink half the cup of your Gatorade, then eat."

"Jim pulled the vibe out of Anna's ass first and twisted it, then shoved it all the way inside her ass. He didn't pull the other vibe out, just moved the control to "ON". Anna held it inside and drank half the twenty ounces of Gatorade. Then she cut the sandwich in pieces and ate quickly. After three bites she was holding the vibe inside her pussy with one hand and grabbing the table in between bites to help hold her self upright. When she had swallowed half the sandwich Mistress Jan asked both men to withdraw the vibes. Master Jim used a napkin to catch the vibe from her ass.

Anna looked at Mistress Jan and said, "Permission to speak, Mistress?" Her body was quivering. She held the edges of the table with both hands.

"Speak." Mistress Jan said.

"Please Mistress, I want to cum for you. Do anything to me and I beg you to let me cum!" Tears of frustration ran down her cheeks.

Mistress Jan stood and pointed to her pussy. "Anna, have you watched me cum? Have I given in to my desire to cum?"

"No, Mistress."

"Get on your knees and lick me, Anna. Taste how wet I am." Anna dropped to her knees and crawled to Mistress Jan's pussy. Without using her hands she pushed her face into Mistress Jan's slit and sucked. Mistress Jan's body rebelled for a second and her back started to arch and the beginnings of a moan escaped her lips.

She stepped back. "Am I wet?" She asked.

"Yes, Mistress."

"Who do you think should cum first, you or me, Anna."

"You Mistress, if that is what you want."

"It is what I want. I want Jim to fuck me to an orgasm, then Pete until I cum again and then I want you to lick and suck me to my third orgasm. If you do well, I may let you cum."

"Yes, Mistress. Thank you, Mistress."

"Clean up our lunch then come to my bedroom. Do not touch your ass or your pussy!"

"I won't touch them, Mistress." She took a breath and said, "Thank you Mistress."

Mistress Jan walked into the house with Jim following. Pete stayed to watch Anna clean up.

When Anna had all the wrappers and cups into the trash Pete said, "Stand here and bend over at your waist and suck my cock."

Anna did not hesitate. She bent at the waist and took Master Pete's cock in her mouth. He fucked back and forth into her mouth until he flooded her mouth with his spunk. He held her head as he unloaded and said, "Swallow it all. Don't forget to thank me."

She cleaned him with her mouth and when he pulled out she said, "Thank you Master Pete for fucking my mouth and for giving me the gift of your seed."

"You did good. Now, go find Mistress Jan and Master Jim."

She went inside and easily found them. They were making plenty of noise. When she stepped into the bedroom Master Jim was standing beside the bed holding Mistress Jan's feet high and wide apart. His hips moved back and forth as his cock slid into Mistress Jan's wide open pussy.

"Come to me, my Pet. Kiss my tits as your husband fills my cunt."

Anna stood beside the bed and bent to her task. Just before her lips touched Mistress Jan she said, "Thank you for allowing me to serve you, Mistress." Then her lips encircled her right areola and nipple. Jan opened her eyes and said, "Start with the other one!"

Anna ran to the other side of the bed and said thanks just before she sucked on Jan's left areola and nipple. Pete moved to Jan's face and she swallowed his partially hard cock. She made lots of noise sucking Pete.

Master Jim loved the scene he watched and participated in. The four were all aimed at bringing Jan off. Jim said, "Where do you want me to cum, Mistress?"

"In my pussy! Deep in my pussy!" Jim had been thumbing her clit and as he came so did Jan. Anna kept sucking on her tit. She had not been told to stop.

Jan calmed for a few seconds and said, "Pete, please fuck my ass. Anna put something under my ass so my pussy doesn't drain of your husbands cum. Then suck my other tit. Hurry!"

"Yes, Mistress. Anna folded a towel and lifted Mistress Jan's ass high enough to get the towel under her. As soon as she moved Pete stepped up and slid his cock into Mistress Jan's ass. She moaned and Pete grabbed her hips and began pounding into her.

Jan reached out and grabbed Anna's hair, dragging her face to her tit. "Suck me bitch! Suck me hard and long!" She held Anna's hair and Jim both saw and heard his wife's moans and slurping sounds.

Pete had cum in Anna's mouth not long before so he lasted a very long time in Jan. When he felt the stirrings of an orgasm he told Anna, "Let go of Mistress's tit and lick her clit." Anna moved quickly to comply, saying, "Thank you Master for allowing me to serve you and Mistress Jan."

Less than a minute later Mistress Jan screamed and came. Her body shook and she thrashed. Pete growled and filled her ass. When he pulled out he held Anna's face to his wife's cunt.

"One more cum and perhaps you can have one too, Pet."

Anna licked, sucked and fingered Jan as if her life and future happiness depended on it. Jan attempted to delay her third orgasm but failed. She screamed, squeezed Anna's head with her legs and pulled Anna's hair as she came. She flooded the bed, herself and Anna.

"Stop! Enough! Spread yourself on the floor." Mistress Jan almost yelled. Pete bent to her and used a towel to gather some of the cum she had spewed on the bed. Anna lowered herself to the floor and spread her legs and arms wide.

After Mistress Jan rested for a minute or two she slowly sat up then stood. She looked at Anna spread on the floor, wet, disheveled, looking up at her hopefully.

She held out a hand and said, "You have done well, my Pet. Come with me. We need a shower." Anna took her hand and as she rose she said, "Thank you Mistress. I'm happy I could please you."

They walked out of the bedroom and into the bathroom. Jim and Pete got busy. They changed the sheets, wiped up the wet areas on the floor and opened windows to freshen the air in the bedroom.

Jim asked, "Do most women react like Anna to their first experience?"

Pete shook his head and said, "Hell, No. She has been incredible! I don't know how or what she did to prepare for this date, but she has amazed me."

"What's going to happen now?"

"We have arranged to meet with three other couples for dinner at one of their homes. Jan let them know that we might not show. It depended on how Anna did. Anna will be the focus of the evening, and we get a great dinner."

"These are people you play with often?"

"Yes. Jan's sister, her husband, two girl-friends from high school and their spouses. We've been sharing dates for twelve years. How many times have you ever cum in one night?"

"Three, maybe four. That was years ago."

They spread fresh sheets on the bed. Pete smiled and said, "I think you may hit a new record before morning. Just relax and enjoy... and save some for me."

"I'd like you to save some for me as well."

Jan walked back into the bedroom followed by Anna nude. Jan handed Pete the red stockings and bra. "Would you toss those into the washer for us? We need them dry and clean before dinner, please. And, Jim's pants need to go in the dryer."

"Yes, Mistress. I will take care of these things."

Jan looked at Jim and said, "Your wife sucked me in the shower to another orgasm. She hasn't cum for hours! Do you think she has been a good enough Pet to be allowed to cum again?"

"She has earned it! I think I would enjoy being in her ass as she cums and Pete would love to be deep in her cunt. That is my suggestion, Mistress."

"I like it!" Jan slipped a finger into Anna's slit and brought it back, wet. "Anna likes the idea too!" Jan directed the trio into position and Anna watched as the two men got ready to fuck her.

They sat on the floor with their legs spread. Jim's right leg over Pete's left. Pete's right leg over Jim's left. Their balls pressed against each other. Jim stroked Pete's cock and Pete stroked Jim's.

"Anna, here is some ass lube. Bend over and I'll get you ready for the boys."

Anna bent at the waist and spread her cheeks with her hands. Mistress Jan spread lube on her pucker and worked two fingers inside her, twisting and pushing in deep. When she was satisfied she pulled her fingers out and said, "Lower yourself until they are just inside your openings. No more than one inch. Understand?"

"Yes, Mistress. Thank you for letting me be fucked. Thank you, Master Pete for fucking my pussy and Thank you, Master Jim for filling my ass," She straddled the men and lowered herself. Pete positioned Jim's cock against her anus and Jim moved Pete's cock into her open vagina. She dropped down, just a little and looked up at Mistress Jan.

"I have done as you asked, Mistress. Thank you. This feels incredibly good."

"Boys, use your hands. Hold her just where she is as she lifts her legs off the floor." They held her at her waist and she lifted her feet off the floor. She was held by four hands and two cocks.

Anna looked up at Mistress Jan and waited. Both men stared at their cocks at the points of entry.

Jan said, "Drop her all the way down." Pete and Jim let go. Anna opened her mouth and gravity dropped her the six or so inches until she rested against the two men's pubic bones, fully impaled on both cocks. When sound finally came from Anna it was the sound of air rushing out of her. Her eyes were wide. Her hands grabbed on to Pete's shoulders.

"Listen to me," Mistress Jan said. "Anna, hold on to Pete for balance. Pete and Jim put your hands under her thighs and lift her up four inches or so. As soon as she is up four inches let her fall all the way down again. Do it until all three of you have cum. Quickly!"

Jim and Pete held her legs and lifted. They dropped her and as soon as she hit bottom they did it again. Jim calculated in his head. Anna weighed one hundred thirty five pounds. Each man was lifting almost sixty-eight pounds. In his head he counted the reps. He wondered how long he could last.

Jan said, "Who will be the last to cum? That one gets something special from Mistress Jan. Make this last! I wish I had a video of this! All three of you look so hot."

Anna finally spoke when the boys dropped her the fifth time. "Thank you all. Mistress for thinking of this. Master Pete and Master Jim for filling me completely! I have never been so filled. I can feel my body getting ready to cum!"

"I'm going to fill your cunt slut. You are holding me so tight I hope my cum can get out of my cock! Use your muscles to suck my cum into your cunt!" Pete was huffing as he spoke. They were at rep twelve.

Jim felt his mind reeling. He was attempting to count, to watch the erotic scene, to pay attention to what was happening to Anna as her protector/husband and he could feel his body getting ready to unload into her ass.

"How many stokes so far?" Mistress Jan asked.

"Eighteen," Pete and Jim both answered. "Eighteen, Mistress."

"Can you wait until twenty-five to cum for me?"

"Yes, Mistress" All three answered although none of them believed they would make it. Jan moved close and bent to Anna's ear. "When you cum, kiss my husband and feel him fill your pussy!"

"Yes," She gasped for breath, "Mistress." She could feel her control leaving, the shudders and spasms began. She heard Master Jim say, "Twenty-four!" and she bent to Pete and shoved her tongue into his mouth as hard and deep as she could.

Pete bellowed and Anna screamed while they kissed. Jim felt Pete's cock unload and that did it for him! His cum shot hot and wild into his wife's ass. Anna leaned back a little and felt pulse after pulse of his and Pete's cum shoot into her body. Her muscles gripped both men and all three slumped together.

Jan gathered pillows from the bed and put them on the floor by the three lovers. She helped them lean over and lie on the pillows. The men slid out of Anna and moved their legs for comfort, still holding Anna between them. Jan covered them with a blanket and all three slept.

Jan made a couple phone calls while the three lovers napped. She spoke to her sister about what had happened so far. Her sister hung up saying she had an emergency and had to go. Just about the time Jan was going back in to wake the three she heard a car in the driveway. Looking out the window she saw her sister running and taking her clothes off. She didn't wake the lovers. She waited for her sister.

She put a finger to her lips to signal Patti to be quiet. Patti dropped her clothes on a chair and followed Jan into the bedroom. Together they gently lifted the blanket from the sleeping lovers. Patti whispered, "She's beautiful! OOOh, so is he! Can I have some of both?"

"Tonight! But if you want to wake Pete you can suck his cock."

"What about his cock?" She pointed at Jim.