Tim was a typical husband. He worked a 9 to 5 job, didn't really like it but the job provided a decent pay. His wife, Janet, was a stay at home mom and she was active a lot of social clubs and activities for the kids. This arrangement worked great while the children were preschoolers but now, they are grown. One is in college and the other has graduated college and is living on her own. Janet has a lot of free time on her hands now.
Janet occupied her time by working out and getting together with her girl friends. One morning, over a cup of coffee at Starbucks, Janet was chatting with her friend Rose about their sex lives. Things have been so-so in the bedroom lately for Janet and she was expressing her desire to spice it up a bit.
"You know Rose, its just the same old sex every time. Even the time that we have sex is the same. Its like clock work... it's driving me insane!"
Rose replied, "Yes, I know, I was experiencing the same thing with Bobby."
"It is soooo frustrating! I find myself daydreaming about other guys when I workout at the gym. I have even been catching myself daydreaming about being with other women when I see a nice looking lady working out," sighed Janet.
Rose giggled and placed her hand on Janet's hand, "Janet, we've all gone through that! It'll get better, honey"
"Oh I hope so, I'm so bored with my sex life right now. What did you do to change it up? Did you have an affair?"
"Heavens no, Bobby and I found some fun things to explore in the bedroom. Lets just say that I control the scene and I love it!"
"Please don't leave me hanging, give me more details sweetie" begged Janet.
"Ok, Janet, but this is just between the two of us gals"
Janet eagerly responded, "Of course! My lips are sealed!"
"Well, one day Bobby was working from home and I went out shopping for clothes. I told him that I'd be driving to Short Hills Mall and that I'd be gone for the whole day. I mean, it is over an hour drive to the mall and you know how I get when I'm clothing shopping!" giggled Rose.
"Oh my god, of course I do! Remember the time we spent hours just looking for the best high heels for New Years Eve?" giggled Janet.
"Yes, I remember that trip well" giggled Rose, "so anyway, I ended up coming home much earlier than I told Bobby because I was getting a headache and just felt like relaxing the rest of the day. To my surprise, I found Bobby at home wearing a pair of my Yoga pants, my sports bra and a pair of high heels!"
Janet gasped, "Wow, that's a sight to imagine! How did you handle it? I had no idea that Bobby was into cross dressing. What did you do?"
Rose replied, "Well, it kind of turned me on, although he did look ridiculous! I told him to get changed into his normal clothes. I wasn't really prepared for that, in the moment. Later that evening, after I had time to process it all, I brought up the topic. I asked him what he was doing and how long he's been dressing in my clothes."
Janet asked, "And what did he say?" as she moved closer to Rose, almost whispering.
"He told me that he's been dressing ever so often for the past couple of years. I was shocked that he had this secret. But I was thinking to myself, Bobby boy, you are going to be in for a surprise now! It was at that instant that the plan started to formulate in my mind." smiled Rose.
Janet could see the smile on Rose's face and the twinkle in her eye, "Let me guess, this is where you spiced things up in the bedroom?"
Rose leaned in closer to Janet and placed her hand on Janet's knee, "Yes, but you'll never guess what I did!" Rose's excitement in telling her friend was contagious as Janet was all ears at this point.
Rose continued, "I decided that I was going to transform Bobby into Bobbi. Bobby was going to become my sissy husband, completely feminized. Of course, when I started to explain the details, Bobby protested, moaned and groaned. I finally told him to shut up and listen. I forced him to take the next day off by calling out sick. After a little bit of back and forth, Bobby agreed. He wanted to know what we going to do but I just kept saying that he'd like it."
"Oh my God, I can only imagine where your devious mind is going" giggled Janet.
"Well, I let his imagination run wild all night. He kept begging for me to fill him in. I juts kept saying things like"
"You'll find out soon sweetie"
"Oh honey, don't worry, you'll like it"
"Darling, don't worry, we'll have a great time tomorrow"
"Needless to say, he barely slept that night. The next morning, I woke up before him and I got to work. I went into the bathroom and laid out my pink bathrobe, pink thong and bra from Victoria's Secret. I also got out my eye brow tweezers, shaving cream, a few razors and some hot red nail polish."
Janet started to really get excited, "Holy cow, I think see where you are going with this."
"Just as I was finishing setting up, Bobby came into the bathroom. We was still a sleepy, especially since he didn't fall asleep easily. When he saw me in the bathroom, he started getting a little apprehensive, especially since I was so giddy with excitement."
"Good morning sweetie, are you ready to get started?"
Bobby responded, "I'm not sure, what are you doing?"
"Just sit down here on my makeup stool, I'm going to start by fixing a few things on your face"
Click here to read Part II