Chloe
Copyright© 2023 by kadudu
Chapter 2
Romantic Sex Story: Chapter 2 - Crossdressing leads to accidental with wifey.
Caution: This Romantic Sex Story contains strong sexual content, including TransGender Cuckold
She felt so guilty about the incident at the bar with Ricky and wanted to make sure I wasn’t hurt and explained that the only reason things went that way was because of the heightened sexual tension that was happening between her and I that night. She explained that with their sexual foreplay, all the drinks she had, things just got away from her and when Ricky showed up she wanted to tease me even more. She did admit that she enjoyed her time with Ricky but really didn’t mean to hurt me or make me jealous in any way. Kate really wanted to make me sexually crazy and enjoy my release as much as possible.
After the sixth time she apologized for that night I had to admit that I wasn’t that upset. Yes I was upset to see my wife go off with another man and it did hurt to see the photos of them kissing on my phone but I explained that all I really thinking about was being able to get out of this cage and finally get some sexual release.
I also admitted that I wanted to continue to dress as Chloe and that I also understood that doing so wasn’t fair to Kate’s needs. One night after dinner we sat on the couch having with a glass of wine and just chatting.
“Kate, I know you feel guilty about that night with Ricky but to be honest with you, I’ve given this a lot thought and to tell you that I want to live with you as Chloe but you can’t enjoy the company of another man is selfish. I know you’ve turned down several dates with Ricky over the last few weeks because of how guilty you feel but I think you should go out with him for two reasons. One reason is that I’m a little concerned about his threat to tell people about our arrangement but the real reason is that I want you to be happy and I saw the way you looked at him and how happy you were when he kissed you that night. I really want you to be as happy as you’ve made me so please consider going out with him next time he calls. That is, of course, if you want to you. I’m not trying to force you but after everything you’ve done for me, I want to do this for you, Kate.”
“Oh Chloe, I love you and thank you for understanding. I never want to hurt you and I’ll think about it if he calls again. I do want to continue to make you happy and make our sex life even better so I want to continue with keeping you locked up. Are you still good with that, baby?”
“Yes, wearing it is a love-hate thing but I really love when you have that control over me and make me do things I would never do willingly. I’ve never been so excited as I was that night at the bar when you forced me to thank Ricky for taking care of you that night. I hated it but at the same time, I had never been so turned on as I was at that moment. Yes, I trust you and I will wear it for you besides, it really does keep me from getting hard and hides me clity under my tighter dresses and skirts.”
Now living full time as Chloe my feminine skills improved and became more natural. Kate now had me in charge of the household which included cleaning, laundry, food shopping and cooking all the meals.
As promised, Kate helped me find my fashion style and I was now in dresses and skirts all the time. The styles were designed to show off my long legs and round butt. The skirts were always short and tight which meant I had to get used to wearing them and not exposing my panties or stocking tops. I learned how to pick things up, how to sit and stand properly, and as trivial as it may sound, I had to learn how to get in and exit an automobile without exposing myself. Kate taught me some tricks and I practiced until I became proficient. She was still very helpful and encouraging me to strive for perfection.
She had easily convinced me to get back into my pink chastity device and agree to let her control my orgasms. After the night of my first release, Kate was so upset with me because I came so quickly that I needed more training and demanded that I wear it all the time and would only get released when she thought I was ready. I noticed that I grew used to the device and was now able to control my erections. I also noticed after 2 months of training that my penis wasn’t tight in the cage any longer and I realized that my penis must have somehow gotten smaller. Between my small soft penis and the small chastity cage, it was very easy to keep it hidden under my control top pantyhose. Wearing it gave me much more confidence when I wore all my short dresses and tight skirts knowing I wouldn’t be discovered.
Kate and I became very close girlfriends over this time and she treated me like a girl at all times, never her husband. She was helpful with my transformation and we constantly shopped, had our nails done, and went out to movies and dinner every weekend. Since my hair grew out she made an appointment at her salon for me to get hair extensions and the results were amazing. When I left the salon I now had a wonderful head of hair, with super sexy highlights. She always doted over me and told me how nice I was coming along but now with the extensions, she was very happy with how I had progressed and became even more encouraging.
As I predicted Ricky did call and ask Chloe out again. Ever since that night Ricky and Kate communicated often. They talked and texted all the time and the amazing part was Kate made it all seem normal to have a male friend even though we were technically husband and wife. At first, I was upset but after our talks I never let it bother me again. I was at peace with being Chloe and Kate having her life to live at the time.
We were shopping for some new bras when Ricky called Kate. She looked at me and asked, “It’s Ricky, should I answer it?”
“Yes, I’ll keep shopping,” I answered. She went to a quiet spot in Victorias Secret and spoke with him for about five minutes and came back to where I was still shopping.
“Everything OK, honey?”
She looked down and kind of shy and said, “Well yes but I’m not sure you’re going to like what he asked.”
“Tell me, what did he say?”
“He wants me to go out with him next weekend.”
“What did you say?”
“I told him I had to ask you if you would agree to it.”
“Kate, I told you I want you to be happy and that you should go on a date with him. I think it will make you happy make us even closer.”
“Wow, I feel funny going on a date with you home alone. Are you sure you would be OK with that?
“Yes Kate, I’ll be fine and home waiting for you to come back to me.”
“Did you think it through? You know we used to be lovers and very close. What if things get heated up between us and well, you know how things can happen.”
“I’m willing to take that chance, Kate. Since I’m living as your girlfriend I know I can’t give you the things you need as a man and I would understand. I can’t be selfish with you anymore.”
“Wow, you really are understanding and a very special girlfriend. I love you and thank you for giving me the freedom to be with a man again. You know what I mean baby. No offense.”
“Kate, I get it and if I were you I would want to have a man to take me out and treat me like a woman all the time. It hasn’t been fair for you and I want to make it up to you now.”
“You’re too sweet, Chloe but now that you’re living a woman full time maybe we need to find you a date to take you out and treat you like the woman you’ve become as well. It would only be fair.”
“As nice as that sounds, I don’t see that happening and I’m OK with the way things are because I still have you, Kate.”
“You do baby, but if you’re really going to live as a girl and totally understand what being a female is all about then we’re going to have to introduce you to some men that will help to complete your
transformation.”
“Well, I’m not sure about that but let’s do some shopping and pick out a nice outfit for your date next week with Ricky.”
“OK, Chloe. That sounds very sexy, I’d love for you to pick out an outfit for my date. I have some ideas about finding you date but let me worry about that and I’ll surprise you.”
I helped pick out a cute thong and lace bra while we were still at Victoria’s, and then found a cute black silky dress that fell to midthigh for her date night. With the push-up bra, we bought the low cut dress revealed her ample breast and with some four-inch heels, the short dress helped to emphasize her sexy long legs. She looked very sexy and would be eye candy for Ricky.
It was fun shopping for a cute outfit for her to wear but at the same time, I had a pang of jealousy thinking that he would be enjoying Kate and her sexy body as I sat at home waiting for him to bring her back. Nevertheless, I stayed positive and encouraged Kate to buy the sexy dress and matching high heels.
On Friday afternoon Kate had a salon appointment and came home looking like a supermodel with some new highlighted extensions and sexy hairstyle She also had a makeover and the evening look was extremely sensual. I felt myself getting hard in my cage just looking at her and I knew that when she was dressed in that sexy outfit that it was going to be impossible for Ricky to keep his hands off her.
“Chloe, it feels so good to get all pampered with a new hairstyle and makeover. I’m so excited to get into that dress and lingerie you picked out. I forgot how much fun it was getting all dressed up and ready for my date.”
Her expression of happiness of getting dressed for her date with Ricky didn’t make me feel overly confident and I’m sure I had a sad expression on my face when she said that. She must have noticed because she took my hand and said, “Chloe, I didn’t mean anything by that except it was fun getting all dressed up pretty. Surely you can understand that. You know how fun it is to buy new clothes and get pretty and I haven’t done it for quite a long time so I was just enjoying the feelings. I didn’t mean to make you feel bad.”
‘Kate, I’m OK, it’s just that you look so pretty and sexy I was just feeling a little lonely. You deserve to get all dressed up pretty and be taken somewhere special. I want you to have fun and as sexy as you look, I know you will.”
“I knew you would understand. I love when you get all dressed up and we go dinner of a movie. You can just see how happy and excited you are when I tell you how pretty you look or some guy flirts with you. You have to admit that being admired by a cute guy or being told how pretty you look is part of the fun of being a girl. You and I will be doing a lot more of that in the future.
Now, this is your last chance because Ricky will be here any minute. Are you sure you’re going to be OK with me going on a date with him tonight? Speak now and I won’t go but if you let me go then you promise that you won’t be upset or pout when I get back? You promise to be my girlfriend and act like girlfriends do after they get back from a date? I’ll expect you to be happy and excited to hear all the details”. “Yes Kate, I’ve already made up my mind and I’ll be OK. I never thought about what to do when got back from your date. How would you expect me to act?
“Oh silly, we are girlfriends and girlfriends always talk about their boyfriends and their dates. They talk about how he looked, how he treated you if he held your hand if I flirted with him if he put his arm around me when we kissed. If he was a good kisser, and well you can fill in the rest.” I then realized it was going to be an interesting night and didn’t answer as the bell rang.
“That’s him. Now be a good girl and let him in and tell him I’ll be right down.”
“You want me to let him in?”
“Of course, you’re my girlfriend and roommate and that’s what girlfriends do, now go answer the door. It’s not polite to make him wait,” she said running back into the bedroom. I stood there frozen in fear and not knowing what to do when the bell rang again.
“Chloe, answer the door. Stop playing around,” she yelled from behind the closed door.
Walking towards the front door I stopped and looked at myself in the mirror to make sure I looked presentable. My makeup was good and the outfit I wore looked nice so I gathered up my nerve and turned the handle and opened up the front door. There was Ricky dressed in a very stylish suit and I had to admit, looking very handsome. He walked in and towered over me as he said, “Hello Chloe, you look lovely tonight. Is Kate about ready.”
“Thanks, Ricky, you look nice as well. Yes, Kate will be down in a few minutes, please come in.”
He confidently walked past me and into the living room and sat down on the couch. He looked over and waved me over to him, “Sit with me for a minute, Chloe.”
Nervously I walked carefully in my heels on the wood floor and sat on the couch next to my wife’s date.
Ricky smiled and looked deeply into my eyes and said, “I wanted to thank you for letting your wife go out with me tonight. She told me all about your desire to live as a female and I respect that and honor your choices. I know it must be difficult to know she will be with an exboyfriend but I want you to know I will treat her with respect and I promise to make her happy and keep her safe. I don’t want you to worry.”
That was something I didn’t expect and was stunned by his knowing I was really her husband and not her live-in girlfriend. I sat there for a few seconds in shock without saying a word and after an awkward moment said the only thing I could think of, “Thank you.”
“Your welcome Chloe and I have to tell you I was shocked when she told me about your current situation but after seeing you I can see you really were meant to be a woman, I mean you’re beautiful and a completely passable. Even your mannerisms and voice are naturally female and if I didn’t know you were Kate’s husband I would have thought you were really her roommate and girlfriend. Well, I’m happy for you and we’re happy to support you. I’m not sure when we will be getting back tonight but I’ll make sure that Kate sends you some text messages so you won’t worry.
Just remember, she’s in good hands and since I dated her for a long time, I know exactly what she likes and needs so I’ll be taking good care of your wife tonight,” he said with a wink and a smile.
Before I could answer Kate came into the living room and Ricky quickly got up to say hello. When he saw her in that short dress with her exposed breast pushing out of her bra he just smiled and took her in his arms as I sat there.
“Oh my god, I forgot how sexy you can look,” and then kissed her as she put her arms around his neck. After a what seemed like an eternity they broke the kiss and Kate looked over at me and said, “Don’t wait up honey, I’m not sure when we’ll be back. Have a good night and if you get a chance can you please do a quick wash of my laundry basket?”
“Of course and have fun. Love you,” I said as they walked out without looking back. My heart was heavy as I watched as he immediately took her hand and walked her to his car. It was clear that my desire to dress and live as a girl had taken its toll on our marriage and I always knew that if I continued to live this lifestyle that there would probably be an impact in our relationship so even though I felt that I was giving my wife up to another man it was always my choice.
Being selfish and depriving Kate of her needs would eventually make her resentful and most likely end in either her leaving me or having to give up my life as Chloe. I realized that living as Chloe was more important and given the opportunity of Kate dating someone she knew and trusted, made us both feel safe.
It was getting close to 3 am and I was starting to fall asleep on the living room couch when I heard his car pull into the driveway. I was waiting up for her to return safely and her text said she would be late and not to wait but I had to be there for her to welcome her home. After about fifteen minutes of waiting for her to come in, I started getting worried and then realized that they were probably talking and maybe even giving each other a good night kiss. For some reason, it didn’t bother me as much as earlier in the evening. Was I already getting used to her being with other guys? I contemplated my feelings when the door opened and Kate came walking into the hallway.
“Hi Kate, welcome home,” I said in a happy tone.
“Oh hello sweetie, I told you not to wait up. We had such a good time that we decided to go dancing after dinner and we ended up having such a fun time at the club,” she said with a big smile on her face.
“Was it like old times, like when you used to date him?” I asked trying to get her to talk.
“Wow, it was much better. I forgot how fun he is to talk to and he was so attentive all night. He opened my car door, pulled my chair out at the restaurant, and made me feel so special all evening. It was so much fun going out like that. We danced and danced for hours and just laughed about old times and really had a good time.”
I hadn’t seen her this happy in a long time and that wasn’t what I really wanted to hear but I really was happy for her. I was happy she got to enjoy herself and get the attention all of us girls crave and long for. To be told how pretty we are, to be treated special, and to have fun with someone you enjoy being with.
“I’m so happy for you, Kate. I’m glad you had fun, you deserved it.”
“That sweet, baby. I’m happy you’re not upset or jealous and I appreciate you waiting up for me tonight,” Kate said as she held my hand on the couch. Ricky told me he had a chat with you while he was waiting for me and told me how nice you were to him. Thank you for being so sweet and I want you to know that you’re the best girlfriend ever. Ricky wants to take us both out to dinner one night this week. I think it would be fun and told him it would be OK, but I can always tell him know if you don’t want to.”
“You two can go without me, you really don’t want me along.”
“Well, it was his idea, baby. He wanted to thank you for being so understanding and special. He knows that there aren’t many guys that would let their wife go out on a date with an ex-boyfriend. I’ll make the plans for us, baby.”
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