The Payback

"Yes, she was clear about that. She was willing to pay for a makeover. I don't have skills in that area but I can help with choosing a dress and getting you dressed, I guess. And anything else you need. I am sorry you have to go through this."

"Hey, if this is what I need to do to get a nice girlfriend and more, it'll be worth it." Rob smiled. The decision was made. Now to execute the plan so he and Tara could be free to develop the relationship. "Tara, please chat with Debby and get her ideas down exactly. This is a one-time thing. No room for errors."

"I know. I'll see what I can do. Will you meet me tonight?" Tara asked hopefully.

"Well now, I'll have to drive you back too. So let's say at least two hugs and kisses should do it." Rob sounded much more cheerful now.

"I don't want a cheap ride. I am willing to pay more in kisses, starting now. I'll try to be there at lunchtime in the canteen." Tara leaned toward Rob, gave him a hug and a light peck in the lips. "I don't think you want to start wearing lipstick to work just yet so I'll save the heavy stuff for later."

"I can't wait," Rob replied as he walked jauntily to his office. He wondered how his conversation with Debby would proceed. Nothing could be discussed in the canteen but he would need to confirm his willingness.

Rob grabbed his soup and sandwich and went to the table he occupied regularly. He wondered if Debby would show up. He only had thirty minutes for lunch. Ten minutes into his break, Debby picked up her salad and joined him. Tara was nowhere in sight.

"Hi," Debby said in that same tone of voice. There was no emotion.

"How are you?" Rob asked politely.

"OK," was the short reply. It was hard to have a conversation with someone who replied in one-word answers. "You talked to Tara." It was a statement rather than a question.

"Yes, we need to work out some details but..."

"Rob agrees," like I told you. Tara just joined the conversation and sat down. "Sorry I am a little late my meeting overran."

"I was just confirming that I agree to do it but we need to work out details."

"Yes, I will discuss the details with Debby. You can drive me home and I'll tell you all. 5.15 at the entrance to the car park?"

"Yes, sure. I'll see you later." Rob picked up the tray and left them. He knew he would be the subject of discussion. He tried to put it out of his mind. He couldn't believe what he had committed to.

There was plenty of work to wade through all the customers that Rob dealt with. But he couldn't concentrate and found his thoughts returning to Tara. She seemed genuinely interested in him and she was easy to be with. It was hard to concentrate with so much on his mind.

Rob kept an eye on the clock and finished on time. He didn't want to keep Tara waiting. He rushed out. To his shock, he saw Debby and Tara. He had no choice so he approached them and greeted them.

"Ready?" he asked Tara

"Debby wants to tell us something," Tara replied.

Debby was looking in her purse and took out a pack of cigarettes. She tried to light one but her hands were shaking. Tara took the cigarette from her and the lighter, lit it inhaling lightly a few times and gave it to Debby who took several deep puffs.

"Rob, Tara told me you agreed to help. I know that what I am asking is not normal but I am at the end. I told Tara that I can arrange everything and we can do it anywhere you are comfortable."

"Yes," Rob said softly. "Debby, to be honest, I don't know how I will feel after this."

"Well, yes, it may take some time. But if I can get over this I'll be able ..."

"Debby," Tara interrupted. "I can take care of the clothes and things with Rob. Send me a picture of a dress you think you'll like. You said there is a salon that could do the makeover so he will look great. We need time to do this so I think Saturday in one week is right. Is that OK? Rob is that OK? So we have some time to arrange this."

Debby was smoking rapidly and had almost finished her cigarette. "OK," she said finally. "I'll text you the salon number and a picture. See you tomorrow." Debby walked away to her car not looking back.

Rob and Tara got into the car. Tara turned to Rob to kiss him. "Sorry," Tara said. "I saw how nervous she was. Her hands were shaking. I know how anxious she is. I was nervous too that she wanted to meet us tonight. I didn't want that."

"OK. So what else did she have to say?"

"Let's stop somewhere and buy some wine. I have a pasta dish I can bake. Is that OK? I can make a salad too."

The journey to Tara's apartment was mostly in silence. Rob stopped at a small liquor store and bought a bottle of white and red. He also purchases some crusty bread and a block of cheese not paying much attention to what kind. Whilst Tara put the lasagna in the oven, Rob opened the wine. He poured out two glasses.

"So, what did Miss Debby demand now?"

Tara looked at Rob. "It'd not too late to change your mind. Debby will have to deal with it. I don't want to be blamed for encouraging you to do this." Tara's eyes never wavered from Rob's.

"Sorry, I am getting more nervous about this. It was my decision only but I need your help." Rob looked at Tara and again repeated. "Sorry."

Tara came over to him and hugged him tightly. "You have a right to be nervous. This is not something a man normally wants. Especially when someone else is dictating the action. You know I will help but it is you that must endure her aggression."

"Thanks. So what does she want exactly?"

"She wants you dressed to the nines as she was on that day. You would have to look good. She will come in and see you waiting for her. Something triggers a reaction and she will then attack you. I am sure you know what that means. She has already described what that guy Brad did to her. So I think she will want to do the same except..."

"Except what?" Rob asked impatiently

"You only have two openings... she has three," Tara replied softly. "But don't think about that now. Let's eat and then I need to measure you so I can get the right size of stuff."

Over their dinner, they avoided the event that they were both dreading. They talked about family and friends; their jobs, interests and lives. It was the first time they had exchanged such details. They had met several times but always in the company of Debby. Even if their kisses had turned passionate, and they shared a deep personal interest to help Debby, they realized they knew very little about each other until now. Whilst the conversation was light, and in parts intimate, the story of Debby was never far from their thoughts.

Dinner over, they stacked their plates and glasses into the sink. Tara held out her hand to Rob. "Need to measure you so we get the right outfits." She led Rob into her bedroom. "You need to take off your clothes down to your boxers. Remove your socks too. I'll be right back." Rob slowly unbuttoned his shirt and removed it together with his undershirt. He removed his socks and shoes and dropped his pants. Tara returned with sheets of paper and a pen.

"OK. First, step on the paper and I'll outline your feet so we get shoes," Tara said.

"Why do we need shoes? I am not going out dressed like that. People will laugh at me."

Tara looked at Rob with a smile. "OK, in that case, you'll have to come back from the salon fully made-up wearing your jeans and T-shirt. People will laugh at you then, right?" Tara laughed. "Sorry, but I think that will look funny. You have a slim figure and with the right clothes, we'll go to the salon, get your makeover and then come back here to dress. You can go to the salon wearing a simple blouse and skirt. We don't need you messing up the makeup pulling a T-shirt over your head. So what's it to be?"

"You'll come with me to the salon?"

"It's the least I can do. I'll see if they can do my hair at the same time. You'll be wearing a wig."

Rob appeared relieved. Tara had a cloth tape and took his measurements from neck, bust, waist and hips. For good measure, she even measured him from neck to knee. "Good job you're not so hairy but we'll need to depilate your body and legs. It'll grow back soon. Now the shoes. Step on the paper."

Rob stepped on the paper. Tara knelt at his feet and outlined the foot. "Your feet are not that big but the width is important. As she straightened up, the growing bulge behind Ron's boxers was evident. Tara looked up at Rob. "Does talking about dressing get you so excited?" Tara asked pulling down his boxers. Rob stood there silent, embarrassed at his now fully erect penis at 90 degrees to his body.

"All the ladies I know don't have this type of thing sticking out," Tara said wrapping both hands around the rigid shaft. "I think I know a way to make it go down. She kissed the tip and moved one hand to his sac, Her eyes never left his as she slowly took it in deeper, salivating to make it slide in and out. It didn't take more than two minutes and Tara's hands went around Rob's behind as he erupted. She kept him there until it was soft. She licked the tip clean and looked up at Rob. "See that's another way I can help you. I hope it was OK. This was just my second time only." Tara rose and kissed Rob lightly as she didn't know if he would be repulsed by the taste. Rob pulled her to him tightly and kissed her deeply. "Thanks," he whispered. "My second time too."

"You've given two BJs already?" Tara asked with a smile. "You're ahead..." Tara never got to finish the sentence as Rob's tongue was deep in her mouth.

It took some time to untangle. Rob pushed Tara onto the bed, lips still locked. He pushed up her skirt and met little resistance. He dove down and found Tara's nether lips enlarged and very moist. Rob inserted his tongue into the slit and slowly licked up and down, then taking her little knob and sucking on it gently. Tara's hands were on his head pulling it into her groin. She moved her hips up as if his tongue were a penis. She exploded with a copious amount of fluid that Rob drank down. He stayed in that position although Tara's hands were no longer holding his head. He raised his head, saw Tara smiling at him and dragged himself up to kiss her. She accepted his tongue with the remnants of her juices without hesitation. Tara could feel Rob's penis growing against her stomach.

"Rob, that was wonderful. Where did you learn to do that? The same place you learned to enjoy BJs?" There was humor in her voice. "I liked it a lot. But..." Tara paused.

"But what?" Rob asked worried he had done something wrong.

Tara held Rob tightly. "I am very happy we did this and I want more. But can we wait till this thing with Debby is over before we go further? "

Rob stared at her blankly, his erection subsiding.

Tara's hands wandered down to his penis. "I would be happy to use my mouth again...and again."

Rob kissed her hard. "You're right. Not long now and we can then relax and enjoy without guilt." He kissed her again. "I'd better go or I will forget what I just said." Rob dressed slowly.

"You have a slim figure and very little hair, "Tara said looking at a naked Rob. "But we'll need to make sure there is no hair anywhere. I know what to get and we'll try that tomorrow. We have time but you'll need to get used to things. I will buy the clothes and stuff at lunchtime tomorrow when I get Deb's pictures."

"Don't go over the top. This is a one-time thing," Rob reminded her.

"Yes, even more reason to make this look good. I know what you have to go through but we can have some fun on the way, can't we? Is that wrong?"

"Not if we both are having fun," Rob replied, kissed Tara hard once more and left.

The next day at lunch Rob was left to his own. He saw neither Debby nor Tara. He wondered if that was a coincidence or planned. He was sure Tara would want to meet tonight. He was amazed by the connection to her and how his life has changed. Whilst he had initially just sought company with Debby in this new town, he had never been excited by her. Sure, he would have gone as far as Debby would have allowed him, but that was a kiss on the cheek. It was a stark difference with Tara. There was a bond that was going stronger by their common goal to resume a normal boy-girl relationship. Rob knew he was in for some pain by Tara's description of Debby's intended action. The dressing up part was like a Halloween exercise although he had never been interested after the age of eight or so. He was comforted by the fact that he wouldn't have to venture out and make a fool of himself. He had to suffer the salon visit but if Tara was with him, perhaps he could pull it off. He desperately wanted this behind him so he could act normally with Tara. He wouldn't feel bad not asking Debby out again or even seeing her again after that.

Mid-afternoon Rob received an email from Tara that she still needed to do some shopping. She suggested they meet at the mini-mall around 6.45. They could have dinner together after that. Tara didn't have a car so Rob assumed she might be with Debby. He wanted to avoid meeting Tara and Debby together as Debby would certainly see the changed relationship between them. He was pleased Tara had made contact.

Rob was there a few minutes early and watched from a corner if Debby was with Tara. He was pleased to see Tara with several shopping bags alone. She greeted him with a one-handed hug and a kiss on the lips. She had several bags without logos so Rob couldn't identify the store.

"So, did you get everything you wanted?" Rob asked. "Was Debby with you?"

"No. We met at lunchtime. Debby will get the dress but I needed some other things so I came alone. Disappointed?" Tara asked with a smile.

"Don't ever say that. I just don't know how I should react if I see her. Maybe OK at lunch with others but alone or with you, I am not sure."

"Don't worry. Debby said she had some calls to make to her home and so would be busy. Frankly, I know she wants to do this but she too is embarrassed she had to ask you."

They chose a small Pizzeria and ordered a pizza they could share with half a bottle of wine. "So what did you get?" Rob asked losing patience.

"Most things to turn you into a beautiful girl. Just a few more things. Will you come back to the apartment and we can take care of the body hair?" Her smile would melt hearts.

"Yes, I'll take you home," Rob replied.

They went to Tara's apartment and she went immediately to the bedroom and put the bags in the closet. "You'll see them soon enough," she said with a laugh. "You'll be wearing them."

It wasn't long before they were in a clinch and deep kiss. "I think we had better start or we'll never get this done." Tara unbuttoned Ron's shirt slowly. His pants were next and soon Rob was standing in boxers and socks. They came off too. Tara removed her blouse and skirt and was now sown to a bra and panties. It was the first time that Rob saw her body almost naked. She didn't have the tall slim figure of Debby but had a nice set of breasts and no fat. She was a very pleasing sight. Tara grabbed his growing penis and led him into the small bathroom.

"You don't have much growth but let's do it right," Tara said donning a plastic glove and rubbed a lotion all over Rob, from neck to toe. Rob didn't see her face but found her gloved finger in between his cheeks right around his puckered hole. "You better keep this area clean and lubricated. You know what she will try," Tara said humor in your voice. She inserted her index finger into his hole and Rob jumped. "Just checking if you had some experience down there," she said. "Now, we'll have to wait a few minutes and then please shower when it starts to tingle."

Rob did as asked surprised that he didn't protest much. For a one time event, it seemed like this was way too much. He would accept the humiliation of dressing up and being 'raped' even. It wasn't rape technically, as he had agreed to be used like that. The tingling started and Rob felt good with the warm water cleansing his body. Tara had left him a large soft towel and the feeling on his smooth skin was intoxicating.

"Tara?" he called out. "I'm ready,"

"Come into the bedroom," came Tara's reply.

Rob walked into the bedroom towel wrapped around his waist. Tara was sitting on the edge of the bed completely nude. She looked at him with a big smile. "I thought you might like to see all after you've shown me all too."

The growing tent in Rob's towel indicated his surprise. "Wow," was all he could utter.

Tara beckoned with her finger and Rob shuffled forward. As he approached the tent became larger. Tara undid the knot and the towel fell to the floor. She rubbed his body with her hands. "Even though you didn't have much hair it feels so much nicer now," she stated. Her hands went to his erect penis and sac. She kissed the tip tightly, her tongue flicking at the slit. She looked up at him.

"Rob, do you know what Debby will expect when she walks in to see you all dressed up and waiting?"

"Will she want to kiss me?" he asked quietly.

Tara smiled. "I don't think so. Remember what she described? Her boyfriend forced his penis into her mouth roughly. Remember?"

Rob nodded. Tara continued, "Well, I have never been forced to do that and neither have you. So, let's see if we can get your mind on that. I want you to hold my head in both hands and then thrust hard and deep into my mouth. OK? Hard and deep as you can."

Rob held Tara's head and gently put the tip between her lips. He slowly thrust in hesitantly. "No," Tara said. "You're supposed to be raping my mouth so hard and fast." She took the tip back into her mouth and looked up at Rob. He looked down at her not really sure how to do this. Tara saw the look; his gentle nature didn't allow such an act. She grabbed his cheeks and pulled him into her mouth deeply, almost choking. She kept up the movement and felt his eruption slide down her throat. She kept it in her mouth, gently sucking as it grew soft. Rob stood there helpless staring back at Tara, embarrassed.

"Rob, I love doing this with you as I said before. I wanted you to know what to expect. Remember, Debby can only do this with a strap-on. It will be hard and never go soft. It may also be much bigger than your penis. I love your size but this will be different for you." She saw Rob's dejected look. He would not hurt anyone. "I knew you would be like this. You're thoughtful and kind and would never abuse a girl that way. But I want you to be prepared. Now, sit on the bed and don't look whilst I get something."

Rob watched as Tara rose and went to the other side of the bed. Her proud breasts and figure appeared in perfect contrast. A few moments later Tara walked in front of Rob who stared at her in surprise. Her right hand was stroking a deep red plastic penis attached to her crotch. "I talked to my college roommate who suggested I get one of these. You don't have to do anything of course but I want you to know what is coming. This will not taste as nice as the one I had in my mouth but it will probably be close to what you can expect from Debby. Interested?"

Rob's face was blank. Even as he thought of the promise he had made to Debby, he never realized that this is how she would look on the night of the planned event. "Remember, you will be dressed like a girl who, under normal circumstances, would be happy to suck her guy off. Try to imagine that your boyfriend gets into a fit and thrusts into your mouth to get him hard." Tara moved a step closer to Rob and positioned the tip at his mouth.

"Open your mouth and salivate and lick the head," Tara suggested. "Forgive me as I have no experience with a strap on. But I am going to thrust hard so you get a feeling. OK?"

The words were hardly out of her mouth when Tara began thrusting hard. Rob choked and tried to accept the unyielding object in his mouth. Tara thrust hard. The plastic penis was just seven inches long but caused Rob to gag. Tears formed in his eyes as Tara thrust several times hard and then withdrew immediately. She sat beside Rob and kissed his tears. "I'm sorry, babe, but it will be easier for you if you know what to expect. Debby wont expect you to enjoy the sucking and swallowing - like I do with your penis. She'll just want to get it wet and show who is in charge." She hugged Rob tight and turned his face toward her. She kissed him tenderly, her tongue slowly exploring his mouth. It took a minute but Rob relaxed and enjoyed the moment. By some strange coincidence, his penis became rock hard again. "Now I can imagine what it looks like from above when your cock is in my mouth." The kisses continued.