The Payback

Tara suggested they meet around 5.15 pm in the parking lot as before. Rob looked forward to that and completed his work promptly at 5. His boss needed to talk to him and Rob rushed through his questions and dashed out to the car park. To his horror he saw Debby standing with Tara. It was too late as Tara waved to him. He wondered what surprise she now had for him.

"Hi," he greeted them anxious to avoid hugging and kissing Tara in front of Debby who was nervously smoking a cigarette. She stamped on the butt as Rob approached.

"Hi Rob," Tara replied. "Debby wanted to suggest something and I thought you needed to decide."

"I wanted to ask if..." Debby paused for a moment searching in her bag. She found her pack of cigarettes and lit one. Her hands were not shaking as much as the last time. Silently Tara grabbed the pack and took one herself and Debby lit it for her. Her nervousness was apparent as she inhaled and rapidly blew out smoke. Rob knew Tara was not a regular smoker.

"I wanted to know if I should reserve a hotel downtown for Saturday. After your makeover and dressing, we could meet in the bar, have a drink and then go to the room."

Rob looked at Debby and then at Tara who appeared really upset. He understood. Tara didn't want Debby to spend more time with Rob than necessary. It wasn't a date. Her looks showed her anxiety.

"Debby, I promised to help you," Rob said finally. "I will dress and do as you want but I don't want to be seen by strangers. It seems I have to come back from the salon to the apartment in a dress. I have never done this before. I think an apartment is best. I don't want to be seen in public." Rob paused. Tara was looking at him and taking a deep drag, blowing out a cloud of smoke. "I would prefer it to be at my apartment then I can change back easily."

"Or we can do it in my apartment," Tara interrupted. "You can change into the clothes you went to the salon in. I promised to go with him."

Debby looked at both of them, smoking for a moment. "I understand. You both can decide where we meet and I'll plan to be there for about 7.30 pm."

"I don't want to be in the apartment when you both meet," Tara said. "I promised Rob to help him remove the makeup etc."

"Yes, I don't want that either," Debby said. "You can wait in my car. I can text you as I arrive so you can sit in my car. Keep your front door open. When I return to the car you'll know I am done." She ground out her cigarette. "I talked to the salon and will give them all that you need. Tara gave me the sizes." Debby left abruptly and Tara and Rob stared after her.

Tara took one last drag on the cigarette. "I know why people smoke when under pressure," she said. "Sorry, but I didn't expect that." She went up to Rob and hugged him and kissed him lightly on the lips. "I am so glad you didn't want to be seen with her in a bar. What the hell was she thinking? She wanted a date with you in a dress?"

"There was no chance of that," Rob said.

"You will only be Robin for me, right?" Tara said linking arms with Rob. "Let's go. I need a drink and some food."

"I told you I'll tell you after Saturday. Yes, I could do with a drink and food. Pizza?"

When they got into the car, Tara gave Rob a long lingering kiss. "Thanks," she whispered.

"For what?"

"Not wanting to go on a date or whatever with Debby. I still can't believe she would want to be seen with you in a bar and then rape you or whatever the word is."

"Yes," Rob replied. "There is more to this than her boyfriend experience. I am sure she has other issues. So you don't think I'll look good enough to go out on Saturday? Robin will not look good?" Rob asked with a smile.

Tara looked at his profile and smiled back. "I think you'd look great with your figure and what all the salon will do to you. I would be happy to go out with you in a dress if you wanted. But then I'd take you home and make love to you, not rape you."

"I think the technical term would be abuse. Since I agreed to let her do it, I don't think it is rape. Either way, it would be what she wants not what I want."

They stopped at a small Pizza parlor on the way. They each had a piece of pizza and a glass of wine. Their talk was about their day and the office. The subject of Debby would come up later.

"Are you coming back to the apartment?" Tara asked hopefully as they went back to the car.

"Yes, if it's OK with you. There is something I need to do," Rob replied.

"Of course. What do you need to do?"

"I'll show you," Rob replied mysteriously.

They entered the apartment and Tara pulled Rob to her and gave him a deep kiss. "This will be over soon," she said. "So what do you need to do?"

"I want to pay you back," Rob said with a smile. He took her hand and led her to the bedroom. "Just sit on the edge of the bed and relax," he said. Tara watched in silent amazement. Rob raised her skirt and tried to pull down her panties.

"I am very happy you want to do that but I suggest we undress a little first, don't you? Then we can relax." Tara stood up and unbuttoned her blouse and unzipped her skirt. Tara was down to bra and panty. She watched as Rob too undressed and was now in his boxers and socks. The tent in his boxers showed his excitement. "What the hell, take it all off," Tara said releasing her bra and dropping her panties. Rob dropped his boxers,

Tara pulled him to her and hugged him tightly. "I can't wait for Saturday so we can do what we want. I am sorr...," Tara started but never finished as Rob thrust his tongue into her mouth. "Rob, I have a feeling Debby knows we have grown close and she will be more aggressive. I saw the way she observed us today."

"You think I should back out?"

"I told you, that's your choice. But expect her to be rough."

"OK, you have shown me what to expect so I guess I'll have to suffer through it."

"Yes, I can't take that away. But it may help if we put that thing in you so you get used to having something in there. If you want, I can do what we did last night."

Rob looked at Tara with a puzzled look. "If you think. It sounds weird. "

"It is, but you may be grateful that you prepared. We'll have to lube you there too so it is easier on Saturday. Don't look so glum. It wasn't so bad yesterday, was it?"

"No, I suppose." Rob looked confused.

"OK, let's do that and..." Tara paused.

"And what?" Rob asked when Tara didn't continue.

Tara looked at him shyly. "When this is over, if you want, you can take me back there too. I never did that before. I have one condition though."

"What condition?"

"First you have to make love to me normally. Then you can do what you want. You don't know how badly I want that,"

Rob smiled. "You mean you want it badly back there?" Tara threw her skirt at him.

Tara lubed and inserted the plug into Rob. It was not comfortable but there was no pain. He knew what to expect on Saturday. Tara sat on the edge of the bed as Ron knelt between her feet. They kissed hard. Rob suckled her breast taking each nipple into his mouth. As his tongue traveled down her body he inserted his tongue into her navel cavity which caused Tara to pull him into her hard. He left a trail of spittle down her body through her pubic hair to her very wet and swollen lips. At the mere flick of his tongue, Tara shuddered. She was close as Rob inserted his tongue between her lips moving upward and finally sucking on her knob. Tara exploded pulling Rob's face deeper into her groin.

"Oh my God," she exclaimed. "That was a volcano. I've never cum like that." She lifted Rob's head, looked at him and kissed him hard. It was the first time she had tasted her juices from a partner. They hugged for a moment and Rob forgot he had something inside his passage. He felt it but there was no pain or discomfort.

Tara stood up and helped Rob stand. "That was incredible," she said kissing him lightly. She then pulled him onto the bed and got on top of him. It didn't take long for them to be in a 69 position. It took some time but they savored the moment and exploded again. They lay like that with their mouths still at the base of the other's groin.

"I'd better go," Rob said rolling off Tara.

Tara didn't say anything and just hugged Rob. "Turn around and bend over," she said. "Can't have you going home with that thing inside you." As Rob leaned over the bed, Tara gently pulled on the disc at his rear passage. The plug came out with a soft squish. "We'll have to lube you well on Saturday but need to make sure the lube doesn't run and stain the dress. The panty can be washed. I may need to get a pad." She slapped his backside lightly. "Nice," she uttered softly.

Debby did not turn up at lunch the next day. Tara did take lunch sitting across from Rob. Except for discreet, accidental touching of their feet their contact was normal. They ate slowly each thinking of the events to come.

"Meet 5.15?" Rob asked.

"Yes, as usual."

Rob looked forward to meet Tara. They had grown close and Rob knew they were well matched. Tara was interested in him, looked after his interests and seemed genuinely to want his company. She also enjoyed sex with him and on Saturday they would break their self-imposed abstinence. Rob looked forward to that. Without Tara, he would never have agreed to this act. He wondered if Debby would have asked him directly.

It was Thursday now and just 2 days before the big event. Rob and Tara did meet and decided that they would just go to that bar where Rob first invited Debby. It was the second time they were alone in the bar. They found a parking spot a ten-minute walk from the bar in a corner by a large dumpster.

"So have you heard from Debby today?" Rob asked quietly. "Any surprises?" Rob was drinking a small beer. Tara wanted white wine.

"No, don't think so. She told me she had dropped the outfit and stuff at the salon and made arrangements for you to change there. I asked what the outfit was but she wouldn't say. She said you would look good."

"If I have to walk out of the salon dressed, I hope I don't look like an ugly hooker," Rob said glumly.

Tara put her hand over Rob's. "First of all, I said I would be with you at the salon. I made an appointment one hour later than you. We should both be done by 5.30 or 6. I doubt Debby will want you looking like a hooker as that means she too would have looked like that. She said that she looked so hot that Brad lost it and attacked her. You may get some looks in the salon or on the walk to your car, but you'll manage it. We can say it's for a prank at a party if anyone asks. We'll take a low heeled shoe to the salon. If Debby wants you in matching high heels, you can wear then when you are back in the apartment."

Rob nodded but was still concerned and mulled over his decision to do this. It was bizarre, weird, crazy and a lot more things besides. But he was brought up not to break a promise. He wanted no guilt in breaking up with Debby but that was illogical: he had never had a relationship with her!

They had a light dinner at the bar. Most of their conversation was in short sentences. In some ways, it was a help to be amongst people. They had already talked about this bizarre plan for many hours. Rob could still back down but he wanted this behind him and there was no way he could face Debby after that in the office. He also worried if Tara might think he wouldn't keep to his commitments. Although she knew his motive and supported him fully, he didn't want her to feel he made such promises - bizarre as the request was - lightly.

It wasn't late when they left the bar and it was getting dark. Tara grabbed his arm. "It'll be over soon," she whispered. "You look worried and tired. You can come back to the apartment or go get some rest."

They reached the car, stopped for a moment and looked at each other. "You're right but I would like to come up..."

They got into the car. Tara turned to Rob, held his head in both hands and kissed him tenderly. "I would like that very much but you need to relax and be ready for this. It'll soon be over." She kissed him lightly again. If you come up, I might not let you go home." Tara's hands roamed down his body to his crotch feeling the growing bulge.

Whilst stroking his hair with one hand, Tara tried to open his pants. Rob didn't hesitate to allow her access and soon his growing erection sprang through the slit in his boxers. Tara stroked him slowly.

"Somebody might see," Rob interrupted.

"It's dark, there is no car near us and who cares," Tara replied licking the tip. Slowly it disappeared deeper into her mouth. Rob stroked her back and tried to thrust deeper. It didn't take long and Rob erupted with a load. Tara's lips were tight around his cock not letting a drop escape. She moved up and down and kept the deflating organ in her mouth. It took some minutes and Tara flicked her tongue at the slit extracting every drop. She looked up. "What a tasty dessert," she offered. "I hope you're a little relaxed now and within a few days, you don't need to go back. OK?" She reached up and kissed him. Some of the ejaculate still on her lips but Rob didn't mind.

"Oh yes," Rob replied.

"Sleep well. Just one more night and we can celebrate." Tara pecked him on the lips and sat up straightening her blouse. Rob pulled up his pants and started the car.

"I'll see you tomorrow. I can pick you up at 7.45 and get a coffee."

"Yes, that would be nice," Tara replied. Rob gave Tara a deep kiss and drove away. He couldn't wait for this to be over. Whatever he had committed to and he needed to endure, he was very sure he had found a great partner and lover in Tara.

It was a restless night and the thought he would meet Tara early cheered him on. She was waiting and greeted him with a kiss. "One more day," she said softly.

They stopped at a coffee shop for coffee and muffins. The short ride to the office was in silence.

"Please check with Debby for any changes. Try to see how long she will need." Rob went to his desk wondering how he could concentrate on the job today.

"Yes, I'm sure she'll call. Don't worry it'll soon be over. Car park 5.15?" Tara kissed him lightly on the lips and walked away. Their mood was polar opposites: Tara was glad it would be over and she and Rob could develop a normal relationship. She thought Rob was a keeper and they had experienced so much together in a short space of time that had brought them even closer. For Rob's part, he was nervous and anxious and unsure about how he would survive all of this.

There was no sign of Debby or Tara at lunch. This was not unusual but Rob's mind strayed to what else Debby might be expecting. He would see Tara after work and then this would be the start of the biggest weekend in his life. That thought made the afternoon bearable.

Rob looked forward to spend the evening with Tara as he shut down his PC and walked to his car. He was feeling a little easier that Tara had not sent any messages with changes.

Thankfully, Tara was alone and they got into the car, Tara turned and gave him a deep kiss. "Soon it'll be over," she whispered. "Why don't we have a quiet meal and then go to my place," she suggested with a twinkle in her eye. "I want you to be completely relaxed."

Rob gave a hint of a smile at the thought. "Sure," he replied. "Any place in particular?"

"How about that food court in the mall? I need a couple of things," Tara replied with an enigmatic smile.

"What kind of things?"

"You'll see. I think you will appreciate it later."

It was hard to be nervous with Tara at his side. He was resigned to do this and put it past him. There were moments when Tara's words and actions caused him to get excited. He didn't know if this was done deliberately or accidentally but each day he was more sure that Tara would be a great partner in and out of the bedroom.

They ate at the food court in the mall. "Why don't you get some wine or whatever and we can meet back here in 15 minutes," Tara said. Tara left Rob to finish his meal whilst she went shopping. There was a small wine bar and Rob purchased a bottle of cold white wine and a bottle of red.

Tara was back within fifteen minutes with two small bags that had no logos. She took his hand as they walked to the car. They drove to Tara's apartment and carried their purchases in.

"You know it's Robin time tonight, right?" Tara asked giving him a small kiss. "You have to be ready and dressing will help. OK?"

Rob nodded glumly. His happy mood suddenly disappeared. "I know," he mouthed softly.

"Don't look so glum. It was fun last time and I remember very well how your little guy was. Think of it as a game between us where we're both having fun." Tara paused whilst unbuttoning Rob's shirt. "I know tomorrow will be different but think about how much nicer it will be for us to enjoy each other without that cloud of guilt. I can't be with you for those minutes but I will definitely be there in thought. OK? Now, let's try to enjoy it." She kissed him lightly and stripped him of his shirt.

The pants and boxers were next. "Your little guy likes the idea, it seems," Tara said holding the growing member in her hand. "Girls don't have these things growing so big and hard at their sensitive spot. We'll have to do something about this, won't we? Well, what I mean is that I can do something and you have to relax and enjoy it."

Rob saw Tara kiss his nipples, trying to take a nipple into her mouth. It was too small. She licked down his body until she was on her knees, looking up at him with his rampant cock at her mouth. A few tentative licks, the head disappeared between her lips and then he was all the way in. She certainly knew how to excite him and within a few minutes, he exploded down her throat. Tara was always insistent to let his member deflate in her mouth with gentle licks and then using the tip of the tongue to extract everything from the foreskin and slit.

"There now, he should stay down a little anyway." Tara rose and kissed Rob who was now used to the taste. "If you need to use the little boys' room do that and I'll get some things out.

Rob headed for the bathroom and Tara laid out some clothes for him. It was a simple dress, bra with panty fillers and shoes. Rob came back a few minutes later and saw the items on the bed. He started to grab the items when Tara stopped him.

"Turn around and hold the end of the bed. You need lubrication." Tara inserted her finger into his anus and pushed in a large glob of a cool gel. Rob couldn't help it and wiggled his bum and invited her finger in deeper. Tara smiled. "Before you pull up your panty put this in," Tara said wiping her finger on a panty liner pad. "I don't think we need the plugin tonight." Tara had a big smile on her face. "I'll be putting something else in there." She kissed him on the lips lightly.

Rob did as asked and felt the soft pad. "This will not only help keep the front flat but will also help absorb any lubricant spoiling your dress," Tara explained as she pulled the panty up and tight.

Tara held out the bra and Rob put his arms through the straps. "I think Debby will have some pads for you tomorrow but I only have panties and hose." Rob buttoned the blouse and pulled up the skirt. Tara had him step into the shoes. "I am sure it'll be a garter and stockings tomorrow but you'll manage fine."

"I wonder what kind of wig she has chosen," Tara said. "You'll look great. Now hold still." Tara applied some dark lipstick, which is what she usually wore. "We'll need to apply plenty of lipstick and gloss to make it easier tomorrow. Now, why don't you walk around on those heels and find your balance whilst I get ready."

Tara kissed Rob lightly on the lips. "Sorry, but I'll try to be rough as I think Debby will be. But I don't really know how to use the strap on too well."