The Payback

"What's this?" Tara said sliding to her knees. "It seems like you enjoyed that. Now relax, I am going to enjoy this." Her mouth slid over Rob's erection slowly and languorously bringing it to a hardness Rob had never felt. When he finally shuddered in climax deep in Tara's mouth, she was looking at him with in ecstasy. She kept him there with slow sucking movements until he was totally flaccid.

"Can I do...?" Rob began.

"No need. You'll get plenty of opportunities when this is behind us. I promise. Well, enough for tonight," Tara said standing up and helping Rob up. She kissed him softly. "You had better leave or this will go further."

Rob got dressed and started for the door amidst several stops for kisses. "Be ready for tomorrow. You'll try some clothes and we may want to experiment back there." Rob's startled look was interrupted with another kiss and a quiet closing of the door behind him.

That night and the following day Rob's mind was on what had happened and what was to come. He had not enjoyed the initial thrusting into his mouth and he knew that Debby would be even more forceful. He was very happy to have support in Tara but wondered if he was crazy or stupid or both to have committed to this. He didn't feel he could back out. With Tara's help, he would see it through and not feel guilty about breaking with Debby. Then, he wondered why as he never had a relationship with Debby. A kiss on the cheek wasn't quite what he expected on a second or third date. The few times they had taken a drink or a meal, Tara was always there and he was glad. He wasn't sure how Debby would react. He knew that he had found a soulmate in Tara. In the short time they had been close, Tara had been more responsive and understanding than Debby had been. It was also a mystery that Debby had never trusted him enough to disclose her anxiety and history to request his help. Instead, she had used Tara as a shield and then as a go-between.

Again at lunchtime neither Debby nor Tara was to be seen. He could understand Debby's reluctance but missed Tara's conviviality. Perhaps they were shopping again but he couldn't imagine what else he would need. This was a one-time deal. In his mind, he thought that the relationship with Tara was more than worth any pain or discomfort he would suffer. He was hoping to hear from Tara this afternoon.

Tara did send Rob a message and asked if he could drive her home. They could meet as usual after work in the car park. Rob readily agreed. The afternoon was a blur. He put the thought of what he would experience next to the back of his mind. He was happy to be with Tara. In only a few days he was consumed with thoughts of her.

Tara met him with a kiss on the cheek. When they entered the car, hidden from co-workers, she gave him a deep kiss with her tongue exploring his mouth. "Can we go to that bar, have a drink and a snack maybe and then go back to my place?" she asked.

"Of course," Rob replied. "Great idea. Missed you at lunch."

"Yes, Debby wanted me to make arrangements at that salon. Rob, we need to make sure you are ready for this."

"What more does she want now? I agreed to do this. You were there."

"I know. I have been thinking about this and what you have to go through. We said Saturday in one week. I would love for this to be over quickly so we can put this behind us."

"What are you suggesting?" Rob asked.

Tara looked at Rob. He was driving so she couldn't see his full face. "Would you mind if we did it this Saturday? I want to get this over quickly and be with you normally," Tara replied softly.

Rob thought for a moment. "Tara, I have no idea what to expect. I will do as I promised. You are right though. Putting this behind us quickly is best for all. I need your help of course."

"I'll send Debby a text. We'll have to get you dolled up sooner then. I am looking forward to see you in a dress. With your figure, you'll look better than me."

"That's not funny and no way would I look better than you. I'm happy I won't be dragged out somewhere for people to see."

Tara laughed. "First of all, you have to go to that salon dressed. Debby will tell the salon the story but you can't scare their other customers away by dressing as a male and then having a makeover. That would make you a laughing stock. Then you have to leave the salon like a lady, come back and get dressed as Debby wants. Then you know what to expect."

"Yes," was Rob's mumbled reply.

"So, still want to go through with it?"

Rob was just parking and didn't respond instantly. He looked at Tara. "What do you think I should do?"

Tara grabbed his hand. "These last few days have been magical. Finally, I have found a happiness I didn't know before. What I am trying to say is that I would like us to be together and see where it takes us. But, this is asking a lot to assuage our guilt. Whilst I feel for you, it is you that has to go through with it. I will support and help you and all fun aside, only you can decide. I will accept you any way you decide." She leaned forward and kissed him.

"I don't know, Tara, I just feel I have to help her. I also would feel less guilty because once she knows about us, we will lose a friend."

"You told me she has not sucked you off and not even kissed you on the mouth, so where does that guilt come from? Do you want her?"

"No, no, no. I told you that Debby and I haven't even talked much. I only met her with you and sometimes alone at lunch. Over the last few days we have grown close and I want that to develop very much - if you want that is." Ron turned to Tara who hugged him and kissed him hard.

"I want that very much too." Tara squeezed Rob's hand. "Let's have a drink and get some Chinese. We can eat in the apartment."

"Deal.." They held hands as they entered the car and drove to the bar. Rob ordered two white wines. He gulped his down and ordered another round quickly.

"Take it easy," Tara cautioned. "It's just 6 pm and we need to do some things tonight. You can drink at my place but you have to drive - or stay," she added as an afterthought.

They sipped their drinks, each deep in thought. "Let's go," Tara said and grabbed Rob's hand.

Tara guided Rob to a take-out Chinese restaurant and ordered two dishes. She had Rob wait for her in the car. It was less than ten minutes to her apartment. They drove in silence again. Tara opened the cartons and served Rob and herself. They still had wine from the day before just enough for two glasses. They clinked glasses.

"So what are you thinking? You've been silent for the last 45 minutes," Tara asked.

Rob looked up from his noodles. "I really don't know what to think. I only know that I would like to spend more time with you without guilt. That may not be the right word, I want to help Debby, but the price she is asking is high. "

Tara looked at Rob for some minutes. "OK, Rob. You have to decide what you want to do. I will support you and be with you whatever you decide. I have told you that. I know how you think and I admire your willingness to help. What Debby is asking is not simple. It is a personal decision. I can't take away any pain or hurt, but I will be with you and try to kiss away your hurt. So decide! Neither you nor I want regrets."

Rob looked at her with confusion on his face. This was the most difficult decision he would ever face. He didn't feel he owed Debby anything, yet he didn't want the responsibility of what she might do to herself. It was made worse by the fact that he didn't want any relationship with Debby in the future. Whatever happened with Tara, he knew he could never have a normal relationship with Debby.

"OK." He said finally. "No more talk. I'll do it if you help."

"OK, finish your wine whilst I get organized in the bedroom. I'll be back soon." Tara left Rob to finish the last sips of wine. He got up and put the dishes in the sink and disposed of the remnants of food. He was determined not to re-examine the decision.

Tara came back into the room a few minutes later. "I laid out some stuff on the bed. So undress completely and wear what's on the bed. I'll be in to help you in a minute." She gave him a hug.

When Tara walked back into the bedroom a few minutes later Rob had undressed completely and was wearing floral panties. The bulge in front indicated his arousal. "Turn around and put your arms through these," Tara commanded and help Rob into a bra. "I don't have anything to stuff those cups with but I can use some panties of mine and pantyhose." A few minutes later Rob had a bust. It wasn't perfect but would get him into the mood. Next came a skirt that was well above the knee and a blouse. Tara kept the top button open and wrapped a broad belt around his waist, hanging low on his hips. "This next part will be difficult at first but you'll get it quickly." She pointed out some shoes with a two-inch heel. "Sorry, I don't wear corsets and stockings just pantyhose. I never had anybody who wanted to see me in them," Tara said shyly.

Tara helped Rob into the shoes and with her arm around his waist made him take a few steps. It didn't take long for Rob to get used to the heels. His gait was not feminine but he was steady on his feet. "I don't know if Debby wants you wearing higher heels but these are good for practice," Tara said. Whilst Rob would not be mistaken for a lady, his slim figure was reasonable. Some makeup and a wig would make a big difference. "Now, this isn't perfect but I am trying to get you used to what Debby would want to see. Open your mouth, please." Tara took out a tube of lipstick and applied it carefully to his lips. It wasn't the dark red she normally wore but a much brighter color. "Not bad but you'll look great on Saturday." Tara paused for a moment. "Do you trust me, Rob?" Tara asked

"Yes, of course. I couldn't do this without your help."

"Well, you may not like what will happen tonight but I assure you it is for the best. "

Rob looked at her glumly and nodded. He didn't understand what Tara meant as she opened d a small draw in her dresser and took something out. She also put on a think rubber glove. Rob's mind wasn't accepting what he was seeing, Tara took out a tube of something and had Ron bend over the foot of the bed holding on to the low wooden frame. "Trust me, this might be uncomfortable but you will be grateful later," Tara slid a well-lubricated finger into his anus. Rob jumped but the finger sawed in and out. "My college roommate advised that this was the best preparation for what is to come. I haven't had this experience but I don't want you to hurt." Even as she was talking rubbing Rob's cheeks with her left hand, her right hand thrust a hard object deep into Rob. He grunted in surprise but wasn't really in great pain. Tara rearranged his panties and skirt leaving the case of the plug seated firmly against his rear hole.

"Now walk around a few minutes and then sit on the edge of the bed. I need to change. When we get into this, I am going to try and act aggressively like Debby might. Sorry, but I don't want you to be surprised and upset. OK?" Rob just nodded and Tara left the room.

Rob could taste and smell the lipstick. It felt strange and exciting at the same time. His erection had grown and he remained hard causing a big bulge at his crotch. He walked around the room and got used to balancing on those heels. He sat on the edge of the bed and waited for Tara. The plug settled itself deeper, but he felt little pain. It was discomfort.

She entered the bedroom completely nude with a big smile on her face. Her hand was stroking that strap on and Rob knew what she expected. "Open wide and suck me off, bitch," she said in a gruff voice. The tip entered Rob's mouth and he tried to salivate and take it in. "Deeper," she grunted and thrust hard. Her hands held Rob's head. Tara pushed in deeper and for an instant, the dildo was buried fully in Rob's mouth. It touched the back of his throat. After a few minutes of this, the thrusting stopped and Tara withdrew leaving Rob almost in tears, lipstick smeared and spittle dribbling down his chin. She leaned down and kissed him lightly on the lips. "So sorry but we don't know how long or wide Debby's strap-on will be. But you can assume she will thrust in hard and impatiently." Rob just nodded glumly. There was nothing to say as he had agreed to this.

"You know what's coming next, don't you?" Rob looked at her with a mournful look on his face, scared. Tara looked at the strap-on. The lipstick marks showed how deep it had been in his mouth. "Not bad for the first time," Tara said with a sly grin. "It was the first time, wasn't it?" Rob looked at her glumly. "Just joking."

Tara applied more lipstick to Rob's lips. She took his hand and lifted him and kissed him very briefly and led him to the foot of the bed. "Hold hard onto the frame," Tara said, raising his skirt and pulling down his panty. Suddenly the plug was removed. Rob then felt something small at his hole and then felt a cooling gel. A moment later the hard tip was at his hole and Tara thrust somewhat hard and in several thrust was deep inside. Except for a grunt, Rob made little sound. Tara moved faster although her movements were not smooth. She was not used to wearing and using such a device. In less than ten minutes Tara withdrew turned Rob around and before he could say anything, kissed him hard. This was the first kiss for Rob wearing lipstick. It felt different and any pain or discomfort was forgotten.

"Oh Rob, I am so sorry," Tara whispered. "I would never hurt you. I just wanted to prepare you for the worst. Are you OK?" she said with her arms around Rob in a strong clinch. "Until yesterday I had never used a strap-on. I don't know what experience Debby has with one or what size it will be."

"I guess I know what to expect," he replied softly. "Can you please keep your promise?"

Tara looked at him with raised eyebrows. "What promise?"

"You promised to kiss away the hurt,,," Rob never got to finish his sentence as Tara pounced on him thrusting her tongue deep into his mouth.

They stayed like that for some time. "Know something?" Tara whispered.

"What?" Rob asked kissing her lightly.

"If you can look this good with my inexperience, I think you will look fantastic with a professional makeover and better clothes - all courtesy of Debby."

"What do you mean?" Rob asked still holding on to Tara. Her hands wandered down and she felt the hardness at his crotch. She pushed him onto the bed. Within seconds she was on her knees.

Tara lifted her head from Rob's hard penis. "I can't talk with a mouth full." She continued to suck and blow, squeezing his sac until her rapid movements caused a massive eruption deep in her throat. She kept sucking softly until he was fully flaccid.

"I mean that Robin could turn me bi," The smile on her face was broad. "Will you be Robin for me too? Not just for Debby." Tara looked up and invited his kiss. Even though she had just swallowed his juices, Rob was not put off. He kissed her tenderly.

Rob looked down at her. She was stroking his penis which speared to be growing. "Are you serious?"

"Well? What do you say? Your little guy appeared to enjoy it."

Rob thought about it whilst Tara gently stroked his penis. He had never had a girlfriend who would bring him to a rise moments after he had erupted. Then again, he had had just one serious girlfriend with whom he lost his virginity. After one or two dates, a couple of kisses, all these girls disappeared from his life. He wished so much that he had met Tara first.

"I'll tell you after Saturday," he replied softly. "Is that OK?"

"I think I'll get a better answer if I ask this little guy. He seems to like my mouth," Tara said with twinkling eyes. Her mouth swooped down on his now very erect tool. "I like him filling my mouth too and can't wait to have him fill my other holes."

Rob couldn't speak he was full of sexual tension, excitement and trying to control himself so he wouldn't end too soon even though he had just erupted. He felt it wouldn't be long. Sure enough, it didn't take long for him to erupt. Tara had managed to get him so deep in her mouth that her nose was buried in his pubic hair. She kept it there until he was soft. "Two nice loads," she finally said.

"I'll send Debby a message to ask if she can do this Saturday. I would like it behind us quickly."

"Thanks, Tara. That would be great and I appreciate the help. I am still trying to digest all of this,"

"I know. Let's get you changed or the little guy might wake up again. I really don't mind but there is a danger he won't want to go home."

"I haven't done anything for you," Rob said hugging Tara. "Can I?"

"I promise you that I will want a lot more after this is over. I want you to relax and even if this is difficult, we will get it behind us," Tara kissed Rob back and helped him remove his clothes. When he was naked, she bent down and kissed his penis. "Till tomorrow, little guy," she whispered taking the head back into her mouth briefly.

Rob dressed and after several more lingering kisses left. He was still thinking about the experiences of yesterday and today. He had not felt the pain as he had expected. He was dressed as a girl today for the first time but he certainly didn't look nor feel like one. He knew he had to look better for this to work with Debby. This was his only experience with a strap-on but he suspected that Tara was being gentler than Debby. Still, he felt better able to imagine what he had to endure. It wouldn't be a loving experience. Yet, with Tara's coaxing, he felt good to simulate what he would experience if he were to fuck any of her openings, especially her mouth. He loved how she got him erect in minutes.

On the short drive back he heard his phone ping. He saw that it was from Tara but he would have to wait to read it. He entered his apartment and read the message. 'Debby says Saturday works if the salon has time for you. She'll know tomorrow. Sweet dreams.'

Today was Wednesday and Rob was pleased it would be over. Whatever the pain or humiliation, he was glad it would be over. He very much wanted to experience more with Tara. He knew she was someone he wanted to get very close to. Rob fell asleep dreaming of himself in a dress and makeup making love to Tara. She seemed to like Robin. He wondered if she would let him fuck her in the arse.

Rob had a hard time concentrating on his job. He wanted to spend more time with Tara and develop a normal relationship. He enjoyed the time with her but there was Debby always at the back of his mind. He had no idea why.

Lunch approached and Rob waited to see if Debby or more especially Tara would be there. He knew sometimes meetings overran and lunchtimes were affected. To his surprise, Debby appeared a few minutes later. She sat at his table and said a brief 'Hello'. As usual, in between bites of her salad, she had that same penetrating look which disturbed Rob. He hadn't realized it before but Debby's stare would put off many a man. He understood her history and wondered if this was the result of her experience or her normal look. She never spoke much so her silence was not a surprise. Just as Rob finished his sandwich, Debby looked at him.

"The salon can see you at 3.30 on Saturday. They will need about 2 to 3 hours to do everything. So we can meet at about 7. I'll talk to Tara." Debby got up and left. There were no surprises but he didn't understand what would take that long. Tara would know.

Rob sent a message to Tara and asked if he could drive her home. Tara didn't have a car and normally took the bus. Lately, Rob had driven her back as they spend evenings together. He wondered what more she was going to make him do tonight. In her company and with her loving help, Rob felt he could do anything to put this behind him. The prize was that he could have normal relations with Tara and she promised to allow him a normal sexual relationship. It sounded exciting.