The Meeting Ch. 03

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Something new to try today.
8.2k words
4.82
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Part 3 of the 3 part series

Updated 10/11/2022
Created 04/20/2006
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Upon awakening the next morning, he found her still curled tightly against him, her head lying on his leather-covered chest. Slowly, softly, he began to caress her long dark hair, causing her to stir.

"Good morning sir," he said as she opened her eyes.

"That was yesterday's game my dear, I have a new one for us to try today," she told him, lifting her head, yawning and stretching.

"What time is it?" she asked as she laid her head back on his chest.

"It's just a little after 8:00 now my dear," he told her as he caressed her soft brown hair.

"Then it's time for us to get up and get going." She lifted herself up until she was sitting cross-legged on the bed next to him, her pussy fully exposed to him.

She slapped his hand away as he made to softly caress her naked lips.

"No, you don't, I have a plan and I want to stick to it, and it does not include us fooling around until much later," she got off the bed as she spoke.

"Stand up my dear and I will help you out of your outfit, so we can take a shower together."

He stood, with his back toward her, as she began to untie the laces of his bustier.

"First we will take a shower and get clean and then I will tell you the rest of my plan."

Following her into the bathroom, his cock long and hard, sticky straight out from his body, like a divining rod looking for water, he got into the shower with her. The commanding tone she had used on him last night was still there in her voice. As the hot water cascaded over them, he began to gently soap her firm beautiful body, paying close attention to her breasts, ass and pussy.

As he was soaping her, cleaning the same places over and over again, she was doing the same to him, focusing on his stiff, hard cock as well as his ass. As she soaped his ass, he was both relieved and surprised that it did not hurt, she had fucked him very hard and long with her dildo the night before and he was afraid that he would be paying for the pleasure he felt then today. Turning off the water they slowly towel each other dry.

"Yesterday it was your turn to serve me. Today it is my turn to serve you, in a way." As she spoke, she could feel the heat building between her legs.

"What am I to be wearing?" he asked her as he stepped close to her. Reaching his hands between her legs, he covered her dripping hot pussy with his hand, pressing his long stiff cock against the soft warm flesh of her lower stomach.

"You of course will be dressed as a woman; I don't want you any other way from now on," she told him as she took hold of his wrist, pushing his hand harder against her now swollen lips.

When he tried to insert a finger into her hot steaming hole, she removed his hand from her pussy and brought it to her face to lick it clean of her juices.

"So what will it be my dear, am I to be a man or a woman tonight."

"I liked you as a man," he bowed his head slightly as he spoke. "I liked it when you fucked me, when you slid your big hard cock into me, spreading me wide. I liked it when you fucked my face, filling my mouth with your hot thick cum."

His cock was standing rock hard out away from his body as he relived what it was like to have her take him for the first time, to make love to him like a woman, like a little cock whore. He reached out his hand trying to put his hand between her legs, as he continued, "But tonight I think I would like it if we made love as two women."

"Later my dear," she took hold of his hand and pushed him backwards.

"I want you to save yourself for later. Right now I have to get you out of the house for a while so that I can clean up around here and get things ready for later," she told him as she stepped away from him, and began to pick up their discarded clothes from the floor.

Disappointed, but more than willing to wait, if it was anything like last the night, it would be well worth a little disappointment. He set into his closet to get dressed. Picking out a sweatshirt and a pair of old jeans, and nothing else, he began to get dressed.

"Oh, no you don't," Beth said as she stepped into the closet with him.

"I wasn't kidding when I told you I don't want you to dress in any other way. From now on you will always be dressed as a woman in front of me or I will leave. Do you understand?" she took the clothes from his hands and threw them into the corner of the closet.

"But you can't expect me to go . . . " he began to stutter, shaken by the idea of going out of the house dressed as a woman, he could feel his heart racing and his face turning red.

"Oh, yes I can expect you to dress as a woman, and I do. If you want your sex life to be wild and include me, you will have to dress as I tell you, or I will leave. You have started something here, something I do not want to give up or change. The next couple of weeks we will figure out exactly how this relationship is going to work, but one consent will be how you dress; like a woman. In fact, I am thinking that you need to get your nails done on a regular basis, starting next week. I am also thinking that maybe we should have something done about your breasts, or should I say lack of, but that can wait until later. For now just resign yourself to the fact that if you want to keep me around you will have to dress like a woman."

"What should I wear?" he asked her after she was done, looking at the floor, as he was unable to look at her directly.

He was turned on and scared at the same time. He loved the way she was taking control, telling him what and how to do things, but the thought of going out in public dressed as a woman scared the hell out of him. He was not sure how to take what she was saying about their relationship, he was not sure he liked her threatening him that she would leave, but one step at a time. All he knew was right now his cock was the hardest it had ever been in his life thinking about Beth being in charge, whether total or partial, and him dressed as a woman all the time. It was almost too good to be true.

"Seeing as I expect you to be gone for a while, and we don't want you scaring too many people, lets put together something somewhat conservative," she answered him as she began to look through his clothes.

After much searching, she finally picked a knee length tight black skid with a slit all the way up to the waist on one side, and a white blouse that was so shear it left nothing to the imagination.

"I think I saw something in your dresser that will work with this," she told him as she exited the closet, crossing the room to his dresser.

As she began to open drawers looking; he stepped out of the closet to stand silently beside her. She wanted so badly to take him right there and then, she was so wet after her little speech to him that her legs were now sticky with her own juices. Finally, finding what she was looking for, she turned to show him.

"You will wear this lace body suit underneath your skirt and blouse. It should not only hide the fact that you don't have much of a chest, but it should also keep that thing hidden. I have also picked out a garter belt and stockings for you and a will get you a nice pair of heels while you are dressing," she grabbed at his stiff hard cock as she spoke giving it a hard squeeze. "Now be a good girl and get dressed. Once you are done I will apply your make up for you."

As she spoke, she turned her back on him, bent to pick up her dirty clothes from the night before and left the room.

As he got dressed she herself changed. There were still a few things in her case that he didn't know about yet. Pulling out a pair of black seamed crotch less pantyhose from her briefcase, she slipped them over her smooth soft legs, before slipping into the high heels she had worn the first day she had arrived. Now that she was 'dressed', she deposited her dirty clothes in the laundry room and headed back to the bedroom to finish helping him get ready for his adventure. She really needed him out of the house so she could get everything ready for the evening she had planned.

As she entered the bedroom, she found him fully dressed waiting for her sitting at his vanity table. Stepping over to where he sat she began to apply his make-up, making him look risqué but not too much like a slut.

"Now my plan is to have you out of the house for at least two hours."

It did not hit him at once what she had said, it was hard for him to concentrate on anything but her exposed breasts and smooth crotch framed by shear black nylon.

Stepping back, she admired his make up as she picked up his wig and set in on his head.

"There my dear, you should have no problem passing as a woman, as long as you don't talk to much," Beth told him as she stepped away from the mirror so he could see himself.

Staring at his reflection in the mirror, he could not believe it was him. He thought he had gotten good at doing his own make-up, but with Beth's expertise, he could truly believe himself a woman, if not for the raging hard on he now had pushing against the white lace of his body suit. As he continued to stare at his reflection in the mirror Beth knelt beside him and slipped on the shoes she had picked for him; the highest set of black pumps he had so far in his collection.

"Now Bobby I need at least three hours to get prepared for your arrival. I would like more, but if you get to uncomfortable on the outside, alone, I will understand." She leaned forward kissing him gently on the forehead, so not to mess up his make-up. "You get going now my little girl and I will see you later."

He stood to leave, swaying slightly on his heals, his heart pounding, his whole body washed in a cool sweat, not sure where he would go, but he would at least give her the three hours she needed; he wanted desperately to know what she had planned for them.

"Now don't forget, when you come back, use the front door and ring the bell. You will be my guest tonight," she told him as she walked him to the back door, opening it for him.

"Here," she handed him her purse, "I noticed you didn't have one. I put all your stuff from your wallet inside and put some lip stick and some other makeup so you can touch yourself up while you are out."

After he was safely behind the wheel of his car, opening the garage door only, he decided he would try to go shopping. His head was still spinning. He might not be thinking too clearly, but it seemed like a good idea. There was a new mall a couple a towns over that he had been wanting to go check out, figuring this was the perfect time to do so, he headed out in that direction.

At every light he had to stop, he would break out in a cold sweat at the idea that someone would recognize him for what he really was. But no matter how his heightened state of anxiety made him feel, he made it to the mall without any problems. Parking his car as close to the front doors as possible, still not trusting himself to be able to walk all that far in the heels he was wearing, his first stop should be to get a pair of more comfortable shoes. He stopped the engine, got out of the car and made his way into the mall.

As he passed the first group of people he saw, a group of young girls, he kept looking back to see if they would stare at him. They passed him without giving him a second glance. The more people he passed, the less they looked at him, except a few men who admired him as he passed, the more confident he became. Determined now to make the best of his little outing, he decided to get down to some serious shopping.

Deciding to keep his current heels, he had gotten more used to walking in them. They still hurt his feet a little, but made his legs look so good, so they would stay. He picked a somewhat crowded store of up to date fashion to begin. Stepping in he began to look through the racks, picking out things to try on as he went. Finally finished with his browsing, his arms full of clothes to try on, he mustered all of his courage and headed for the dressing rooms, knowing he would have to make some contact with a sales clerk.

As he closed in on the dressing rooms, a very young and pretty sales clerk moved to intercept him.

"Would you like to try those on?" she asked as she pulled next to him just as he was at the entrance to the dressing area.

Unable to bring himself to speak, knowing that it would give him away. He nodded his head, while at the same time laying his hand against his throat.

"Sore throat?" the clerk asked.

He nodded, thankful that she had pick up on his signal at once, saving him from speaking at all.

She smelled so good. She was young and very firm in body. She was wearing a tight little mini and a white blouse similar to his, but she was wearing a black lace bustier underneath, forming her breast perfectly. He could feel himself stiffening as she continued to stand next to him.

"I know how that is," she said as she led him back into the dressing area, unlocking one of the booths for him.

"I had the worst sore throat last week myself. It was days before I could talk right again. You're probably better off not even trying to talk. Me, I can't help but talk. Gab, gab, all the time. If you need any help, my name is Jennifer and I will be right outside, you can just come out and get me," she told him as she held the door open for him, before moving back out of the dressing area.

His arm brushed against her perk breast as he stepped passed her, making his cock spring to attention. She was very attractive; she looked very similar to Beth.

For the first time today, he got to see his entire reflection in the full-length mirror covering the one wall of the dressing room; he was beautiful. The combination of his outfit and the excellent make-up job Beth had done, he looked every bit a woman. Feeling much better about the whole thing he began to undress and try on the clothes he had picked out. He liked every outfit he put on but he knew he would have to settle on just one or two. He didn't have a lot of money to spend and he didn't what to explain why his credit cards had a man's name on them.

He finally decided on two separate outfits. The first was a dark blue spandex micro dress, very plain for the most part, but he loved the way it hugged his body. The other was a pair of skintight hip hugger blue jeans, which if he still had pubic hair, would show the top of it and a white half shirt that would show off his flat stomach nicely. Collecting his choices he exited the changing room, leaving the rest of the clothes behind. When he exited the dressing area, he found that the shop had cleared out and only Jennifer was behind the counter.

"You found something you like?" she asked him as he stepped toward the counter.

Nodding his head, he set his choices down on the counter, taking his purse from his shoulder.

"I have the exact same things," Jennifer commented as she rang up his purchase. "They should look just great on you."

He inclined his head to her, in recognition to her compliment. She told him the total as she put his purchases into a bag. Reaching into his purse, he counted out some money and handed it to her. As she went to take the money from him, she stopped for a moment, looking at his hands, before taking the money from him. As she counted his change from the cash register, she was staring at him, as if trying to decide something, causing him to break out in a cold sweat. Taking a pen from the counter, she wrote something on one of the bills before handing him the change.

Slowly she counted out his change, placing the bill that she had written on in his hand last, writing up.

"That's my phone number," she stated, again looking at him dead in the eyes. "Just in case you might like to get together."

He didn't know what to do. He took the change she had handed him and shoved it into his purse, breaking eye contact with her as he did.

"I sent everyone else to lunch, just incase I was right about you, and when I saw your hands, I knew I was," Jennifer told him as she stepped around the counter to hand him his bag, moving so close to him that her young pert breasts were pushing against his arm again causing his already stirring cock to harden; it was very exciting to be 'caught'.

"I know you're a man," she told him as she leaned closer into him. "And I really like men who dress as women, it's a really big turn on to me, and you have to be the prettiest man I have ever seen. I almost missed the fact you were a man. Your hands were the give away. They are slender and very feminine, but women's hands just aren't that strong and look that way at the same time." Moving back away from him, she held out his bag to him.

"So if you ever feel like an adventure, you can give me a call or show back up here, and we could have some fun, maybe."

He took the bag from her as she stepped back behind the counter, as a customer entered the store.

Turning quickly, he exited the store, not sure what to make of what just happened, but very excited by the whole thing, so much so he had to carry his bag in front of him to help hide his swollen member.

He spent the rest of the day shopping, trying on outfit after outfit, in store after store, repeating his sore throat routine to every sales clerk he met. Not one once questioned his gender, most barely took the time to talk to him, since he could not talk to them.

By the time he was ready to leave the mall, he had spent all of his cash and had wasted a total of six hours, Beth should be happy. She had called earlier to check on him, and when he had told her he was having a great time; he didn't tell her about Jennifer yet, they had agreed on a new time he should be home.

As he made his way back out of the mall, he realized that he was going to have to pass the store where Jennifer worked, throwing caution to the wind. He was now very comfortable dressed the way he was. He decided to stop by the window to she if she was still working. As chance had it, Jennifer was in the window changing the mannequin. Catching her eye, he motioned her to meet him by the entrance to the shop. He had decided, when he saw her in the window, that he would talk to her and tell her a little bit about his situation with Beth. Who knew maybe her and Beth would be open to a threesome with him in the middle.

"I just wanted to tell you thank you," he said as he leaned in close to her ear, making sure she was the only one that could hear him speaking.

The smell of her perfume, the heat of her body as he drew near to her, made his cock begin to stir for the first time, all afternoon, since seeing her earlier.

"Thank you for what?" she asked, also keeping her voice down, leaning closer to him.

"For the compliment you gave me earlier. Today is my first day out as a woman, and when you recognized me for what I truly am, I didn't know how to react, but your kind words and compliments gave me the nerve to shop all day. I just wanted to stop and thank you for that and to let you know how flattered I am by your invitation. I would seriously think about taking you up on it but I have a situation right at the moment that I am committed to."

Jennifer was standing so close to him now, her breast were pushing against his arm, making his cock so hard, he had to look down to make sure it was not showing.

"Well I tell you what, if your 'situation' ever changes or if she might like to add someone, give me a call or the two of you can come shopping one afternoon."

He could feel his cock throbbing, as she pressed hard against him to kiss his cheek

"Well, I've got to get back to work," she told him as she stepped away from him. "Just think about what I said."