Hit the Button Pt. 04

Part 4 continues. This story is a Cross-dressing and Loving Wife genre, so if that's not of interest, please don't continue reading. I don't want to offend any of the readers.

Thanks for the nice reviews. This has been fun, as the story seems to write itself. (Sorry for any grammar errors, I haven't found an editor for this genre)

Part 4: Back from the Beach Weekend

The night after we returned from the weekend with Dawson and Peter, Lisa and I shared a bottle of wine after dinner and discussed everything that happened over the weekend and how we would move forward.

"That was an amazing weekend, don't you agree, Lisa?"

"Yes, I think we both had a good time, but I'm glad to be home and back to normal."

"Sweetheart, one of the greatest things about our lives together is that we are always honest with each other, and we both know what the other is thinking or feeling. But to be honest, after this weekend, I can't say that I'm really sure what you're thinking or feeling.

Seeing how happy you were to be with Dawson this weekend, and how you explained your feelings for him, has me concerned. If I had not agreed to dress as a female, I don't believe your friendship and feelings for Dawson would have ever happened. I blame myself for putting you in that situation, and I think it's time for Jason to come back. The thought of you having feelings for another man has troubled me, and I don't know how to deal with the pain."

"Oh my god, no. I was afraid you might feel this way after what happened this weekend, but I don't have those feelings for him or anyone else. It was only because of our situation over the weekend. Please let me explain, honey.

I was so excited about us just roleplaying as girlfriends that I too found myself thinking that way. When I convinced you that we should act as my girlfriend this weekend, I let myself do things I would never have done, and I feel so guilty and bad now, especially now that I see your pain.

Coming back as Jason because of the weekend we just had would be a terrible decision. Amanda, have you enjoyed living as a girl since we started?"

"Yes, it's been wonderful. I know it never would have happened without your help, and for that, I will be forever grateful, but I won't jeopardize our love, and I'll be happy to give it up to keep things as they were."

"You don't have to worry about that, and I want Amanda to stay around for a little longer. I can't tell you how fun it was to have you as my girlfriend this weekend, and I want to spend more time that way if you'll give it a chance."

"I admit, it was an incredible weekend, and if there was a way to continue that would allow me to feel confident about things, then I'd love things to continue a little longer.

But there's something else that I'm having a hard time getting over and I know I had a lot to do with it. When I heard you describe Dawson's cock, how big and beautiful it was, how you had to have it in your mouth, how you loved the taste of his cum, and that you had to do it again that night, has given me so much to think about.

All day I've been thinking about it and concluded that I've been depriving you of your basic female needs. Think about it, I can't even get hard anymore and give you that natural pleasure. You said he's bigger than me, and from what you said, you really loved his cock. As Amanda or even Jason, I can't compete with that. Can you understand why I'm concerned?"

"Baby, I don't want you to compete with him. I never intended to have any feelings for him. But when we were alone, my body responded and the sexual feelings were overwhelming. There was never a thought about him sexually until we were alone in that romantic cove. I realized then, at that moment, that I missed being with a man that way. I'm sorry I said those things about his cock, but I haven't seen a hard cock in many months, and never one that big. There's no way for me to explain those feelings or understand how I felt unless you were in my position.

Please believe me when I say I don't want to be with him, you're my only love and I don't want Jason to come back just yet. This is probably me being selfish, but I love having you here as my girlfriend, and I want Amanda to stay around for a little longer. Be honest, do you want Jason to come back?"

"No, I enjoyed every second and our time together, but if you need a hard cock, I don't want it to be anyone's but mine. I know you need that connection, I understand, and I'm partly to blame for putting you in that position. But it hurt to hear how much you liked it, and how wonderful it was in your mouth. I can't get those words out of my head."

"Baby, you know how much I love you, don't you? I need you to know that I only want you, and what happened was because of the situation we put ourselves in. We both got into roleplaying as girlfriends, and I know that had everything to do with my behavior."

"Of course, I know you love me and I'm not mad, it's just difficult to explain my feelings. I'm not jealous, I guess I'm scared of losing you."

"That won't happen, you're stuck with me forever. Now, will you let Amanda stay around, baby? "

"Yes, for a while. We'll see how it goes, but you need to tell me if any of those feelings you had for him come back. Promise?

"Of course, I promise, you know I tell you everything, and I'm so happy Amanda is going to be here for a while longer," she said with a big hug and a kiss.

"One thing I think we need to do is to go shopping for some toys to play with. Now that we both realized that those needs have surfaced, I want to make sure you're satisfied and not looking elsewhere. Let's go shopping for some toys after work tomorrow, I think it'll be fun.

"Oh, my goodness, that's a great idea, and shopping for toys with my girlfriend will be a hoot. I love the idea."

XXXX

Amanda's thoughts:

After hearing her describe his cock and seeing her sexual desires, I knew we needed to find a solution. Either I came back as Jason, which I wasn't ready for, or come up with a way to give her what I wasn't able to supply. For my own sexual needs to overcome my lack of erections, I read how others in my situation could use devices that allowed relief with prostate play or milking. My solution was to get some sex aids to help both of us in order to enhance our sexual play and satisfy our deeper needs.

The next afternoon after work, we dressed in cute skirts, stay-up stockings, and our highest heels, and headed to the adult store across town. We walked in holding hands as two girls, and in our short skirts and heels turned several heads as we shopped for our toys. After telling Lisa about prostate milking, we shopped for a solution and found a section with several options. After reading several packages, Lisa picked out two items and handed them to me as we headed for the dildo section.

There was an extensive selection in all sizes and colors, and this time I picked out two of them I think she would enjoy. I selected a seven-inch vibrator with realistic skin and a large 1ten inch cock with a two-inch girth. While on our way back to pay for our choices, we passed a section with some costumes and Amanda pulled me over the rack.

"Amanda, look at these cute outfits. I just had a great idea, and let's see if they have what I'm looking for." That's when the older saleswoman came over to help.

"What are you looking for, honey?"

"Do you have Playboy Bunny Outfits?"

"We do, but it's on the other rack, follow me."

Amanda found two in our sizes, one in Red and one in Purple. The one she tried on fit perfectly and then got the red one in my size, knowing one size larger would fit, as always.

"Honey, you're looking at our costumes for Halloween. In less than 8 weeks, you and I will be Playboy Bunnies for the Halloween party. Won't that be fun?"

I had to agree because it was something I always wanted to wear. "What a great idea, you're so much fun and this is another reason I love you so much."

"On the way to the register, Amanda saw a French Maid's outfit on display, turned, and smiled at me. I just had another good idea, and I'm treating you to that outfit."

We couldn't wait to get home with our new toys, and when we got back, we rushed up to the bedroom and opened the packages, cleaned the toys, and sat on the edge of the bed, putting batteries in the seven-inch dildo.

After making sure it worked, I smiled and gave Lisa a sexy kiss as I ran my hand up her skirt and under her panties. She was already wet, as my fingers easily slipped inside her pussy. I had her stand in front of me and remove her skirt and blouse, leaving her in just her panties, bra, and heels.

"You look like an angel, Lisa." I said as I removed her bra and started sucking on her breast and playing with her pussy. She pulled my head to her chest and moaned with anticipation. For the next ten minutes, I teased her pussy, sucked on her nipples, and then laid her down on the bed. I removed her panties and tenderly licked her cute pussy lips and her clit, which was now poking out from her pussy lips.

After years of kissing her pussy, I knew exactly how far to take her and brought her to the edge several times, until she was begging me to let her come. That's when I picked up the dildo, turned on the vibrator, and placed it gently on her clit.

Her reaction was fun to watch. She tensed up and had a big smile on her face as her moaning and wiggling increased. After a few minutes of this, I placed the head of the dildo at her entrance and gently pushed inside, as it continued to vibrate. The sounds she was making told me she would not last long, and that was when I pushed the cock inside her pussy. She opened her eyes and let out a yell as I started fucking her with the vibrating cock. I saw tears fall from her eyes as an intense orgasm overtook her, and then watched her buck and scream for almost a minute until she collapsed on the bed with her head thrown back and her eyes closed.

"How was that, baby?"

"It was fucking amazing. I didn't realize how much I missed that. Thank you, I needed that."

I didn't have a chance to undress, and I was still in my skirt and bra as we lay there and cuddled as she played with my padded bra. We kissed and touched each other as she came down from the feeling of having that cock inside her pussy.

Later that night, after showering, we watched some videos and figured out the best way to use the toys for my prostate milking. It took some time and with some practice and patience; I learned how to relax and take the penis-like device inside and allowed it to vibrate my prostate. After several tries, I had my first prostate orgasm. We watched several drops of fluid drip from my soft cock as I sighed in relief. Lisa loved this and as soon as I started to leak, she put my little guy in her mouth and took all I had to give.

After that night, we spent lots of time at the gym and worked on our legs and butt. I dropped a few more pounds, which allowed me to wear some tighter jeans and dresses. Lisa looked drop-dead gorgeous, with her thin waist and perky tits. We both had long legs most girls would kill for, and now our butts were getting tighter and looked even more inviting.

Lisa purchased some new outfits that were much shorter and sexier than before. She said she wanted me to experience what it's like for girls when they wear those types of clothes. She also wanted me to understand how men treat us differently.

Last week she had me wear a tight leather skirt that was over six inches above my knees. Since the evenings were getting cooler, I was now wearing pantyhose all the time, which I loved. After I told Lisa how much I enjoyed how it felt wearing them, and how I liked how my legs looked, I came home to a draw full of a dozen packages of pantyhose in different colors and denier. Lisa never missed an opportunity to support me and do special things like that for me.

Friday night at the club, wearing our new sexy outfits, Lisa and I got so much attention from the men that it became comical. We never paid for a drink, and we danced all night. I told Lisa that my ass was pinched and rubbed so much that I thought the leather on my skirt was going to wear off.

There were several times when we were sitting with a guy and allowed them to run their hands over our legs. I admitted to Lisa that I loved the feeling of a powerful hand running over my nylons and that several men commented on how sexy they felt. Yes, I discovered I loved wearing pantyhose, and that was something that I would do more often.

Lisa had several men coming on to her, and I watched in amusement as they tried to seduce her. Several times I caught them touching her breast, and since she didn't wear a bra that night, they were quite inviting. Seeing her nipples poking through her thin top, and being dressed as I was, made it an interesting and fun night.

We always finished the night lying in bed in each other's arms, kissing, fondling, and experiencing mind-blowing orgasms. We were all smiles.

Things were great at work, and at the office, and I became one of the girls. At lunch, they often asked me about make-up ideas or fashion tips, because I was now considered the diva of the office. They teased me but always complimented my appearance because of the amount of care I put into my clothing and overall feminine presentation. Just dressing as a female was not the goal. Lisa and I wanted full transformation and acceptance in my new role.

I had noticed how the other girls started dressing nicer for work and even started wearing dresses and nylons. My boss Tom was pleased, and even mentioned that my appearance had created some competition with the other women and had elevated the overall appearance in the office. Tom put me in for a promotion because of the amount of work I was handling and being the only trans-engineer in the company helped get it approved by corporate.

Lisa was doing well at her firm but was not interested in putting in long hours or becoming a partner. She was content with handling cases and the work that allowed her to spend more time at home. Things were going perfectly, and all my concerns and worries had melted away.

For the next six weeks, since our weekend on the beach, Lisa avoided lunches and spending any time with Dawson. When we first got back, she explained how she started having feelings for him and realized she had to stop seeing him for a while.

Dawson knew she had feelings for him on that trip. The two blow jobs she gave him that day gave him hope for a closer relationship. He was disappointed at hearing that she needed to cool things for the time being, but he understood how that could happen, knowing how close she was to her husband. He was going to wait and be patient. I noticed the decreased communication with Dawson and brought it up one evening.

"Lisa, I noticed that you haven't had lunch with Dawson lately, and you haven't been texting him, either."

"You're right, I haven't, because I realized I didn't need that in our lives. The only feelings I need are the ones I have for you, baby. I told you everything would work out, and I'm so happy you continued to keep Amanda around for a while longer.

In fact, I want to play a little this weekend, if you're up for it. This week, I want to stay in on Friday night and get up early Saturday. I'm in the mood to be pampered by my housemaid, Fiona. By the way, you're going to be Fiona, and you'll be wearing that cute French Maid's outfit all weekend. Are you up for some fun?"

"Of course, you know I'm up for anything."

"Well, I hope so because as my maid, you'll be doing all the housework and whatever I ask. I'll be your mistress for the weekend, and you'll get to dress up all pretty and spend the entire weekend as my servant. I can't wait."

Friday night, we watched movies and made love before going to bed early. She had me up and in the shower by 7:00 am and helped me into my uniform as soon as I was done. The uniform called for a black corset, with six clasps for stockings.

Lisa held it up and I could tell she was excited to help me put it on. After she tightened the laces, my waist was smaller and my now swollen breasts were pushed up, which gave me the appearance of cleavage. In the mirror, the corset gave me a nice hourglass figure.

"Wow, with that corset you actually have breasts, and you look amazing. You need to start wearing that with some cute tops, and let you show off a little more skin when we go out next time."

The fluffy white lace panties slid up over my seamed stocking tops and looked so cute in the mirror. The white lacey crinoline slip was next and fluffed out at least twelve inches all around. When the black French maid's dress was in place, the slip pushed the skirt out far enough to give the appearance of a very sexy maid. Lisa handed me my black high heels and then sat me down at the makeup table.

For the next twenty minutes, Lisa did up my face and added dramatic eye makeup, added some earrings, and pinned the lace maid's cap into my hair. After spraying some perfume on me and examining her work in the mirror, she handed me a gift box.

"This is for you, Fiona," she said, smiling and handing me the box. She watched all excited as I opened the box to find a gold necklace. When I held it up, the necklace displayed the name Fiona in large fancy lettering.

"Fiona, you're going to be the prettiest maid in the neighborhood."

"Well, I do look cute, and thank you for the pretty necklace."

"OK, Fiona. Until tomorrow night you are my maid and right now, I want you to go down and prepare breakfast while I shower and get dressed."

"OK."

"No. My maid will address me as Miss Lisa."

"OK, Miss Lisa."

"I love it, this is going to be so much fun."

After I cleaned up the kitchen from our breakfast, Lisa asked me to vacuum the house and do the laundry while she went out shopping and to the gym. That night, Lisa lifted my slip, removed my pantie, and for the first time ever, used her seven-inch dildo on me.

She had me on the bed on all fours and said she wanted to milk me again. With my head on the pillow and my ass up in the air, she lifted the dress, and the crinolines, and lowered my panties. She was off the bed and told me to stay in that position.

"Stay like that while I get the lotion for your little toy."

I stayed there for a few minutes, exposed and waiting for her to come back. She got up on the bed and started putting lotion on my opening, and started teasing my hole with her fingers.

"Do you like that, Fiona? Does that feel sexy?"

"Yes, oh my god it feels great. Please keep doing that."

And she did, she put two fingers inside me and started stroking them in and out as I moaned in pleasure. Then she pulled her fingers out and put more lotion in my boi-pussy. I was loose and lubed and ready for my toy, but Lisa had other ideas.

I felt her move between my legs as she pulled my ass higher into the air, and then felt pressure at the opening of my rosebud. It felt much bigger than my toy, and I soon realized she was pushing her seven-inch dildo into my opening.

"Just relax baby, I want to do this, and as my maid, you have to do what I want. Isn't that right, Fiona?"

"Yes, Miss Lisa," I said, as I was waiting to see what she was going to do.

She continued her pressure until the head of the dildo slipped inside me and I yelled in pain. She told me to just relax and didn't move until the pain stopped. After a few minutes, she started with more pressure, and then I felt it slide all the way inside. I felt her body pushing against me and realized the cock was completely buried inside me. She pulled back, and the dildo slid out, and that's when I realized she had a strap attached to the dildo and she was now fucking me.

"Do you like getting fucked like a real girl, Fiona? Does my little maid like my big cock? Answer me, Fiona!"