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Caught And Wondering Where My Life Will Go

"I was sitting at home alone feeling very sorry for myself. My wife and I had not been getting alone lately – constant arguing and absolutely no sex."

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2.4k words 2.4k words

Author's Notes

"This story is fiction although it is based on the experiences of people I know."

I was sitting at home alone feeling very sorry for myself. My wife and I had not been getting along lately – constant arguing and absolutely no sex. It was not a busy day at work, so I decided to take the afternoon off and come home. I had hoped we could sit down together to talk through our problems. I had not called to say I was coming home and thought I might please her with a surprise bouquet of roses. When I arrived home, she was gone. There was no note - she was just gone. I wandered around the house looking for her and all I could see were the leftovers from her dressing – makeup out, hair things out on the counter in the bathroom, and several outfits that didn’t make the cut for her planned activities. Also on the bathroom counter was her wig.

I got myself some lunch and sat in the family room to read, but I had no concentration. At some point, I went back upstairs to the bathroom. I looked again at her wig over on the counter. I had always liked the way she looked when she wore it, and actually a little glad, she had not put it on for this afternoon trip. Then, out of the blue, I decided to try it on myself. I had never done anything like this. My own hair was short, so I easily slipped the wig onto my head. Looking at myself in the mirror, I actually looked good – different from my wife, but definitely feminine and actually attractive. I wondered what I would look like with her makeup but was very much afraid to try that.

Wearing the wig, I wandered the house. First, I tried on a pair of her mules and walked around. I was very surprised that I could walk in the heels. Then, I saw her discarded things on the bed. I had to try them. I discovered that her skirt fit although it was very short on me. Then I tried the matching blouse which was too – tight but I could get it buttoned. I felt so different. I walked around the upstairs. I swayed. I pranced. I got into one of the bedrooms with mirrors so I could see myself. Wow, I was not myself, but I looked very much a woman.

By now, I was very much excited. I moved over to a stool in front of my wife’s makeup table and sat with legs crossed like a perfect woman. I have no idea why I say it like that, but it just seemed natural. I looked at myself in the mirror and I was actually pretty. At that point, I was completely aroused and excited. Sitting on her vanity stool, I slipped my underpants down, and started stroking my very hard cock. I was so ready, and it wouldn’t be long. I stopped stroking to get a towel from the bathroom. Returning to the bedroom, I started stroking again. I could see myself in the mirror but was lost as to who I was seeing - I was a woman but I had a cock!

I was just about ready to cum when I heard the garage door opener start. Wow, was I in trouble. Here I sat wearing my wife’s things, stroking my cock and she was coming in. There was no way I could ever hide or get out of these things before she found me. As I stood to go to the bathroom, she appeared at the bedroom door and screamed. Horror, I was caught, and she was even more upset than I had ever thought – well, actually, I obviously had not thought at all about what I was doing but rather wanted to cum.

Of course, I tried a lame explanation; but she was having nothing of it. At that point, I was so ashamed and embarrassed. I would have done absolutely anything to appease her. She calmed a little, removed her cell phone, and took several pictures of me wearing her things. Thankfully, I had enough sense to get the skirt down and not expose my cock. Then, she told me to stay in the bedroom and stay dressed. She was going out to think and we would deal with this situation later when she returned.

I was at a total loss as to what I should do. My initial thought was to get out of her things and perhaps she would be calmer when she returned. However, she had been very specific that I was to stay dressed. I stayed in the bedroom. Time moved by very slowly. It was now over two hours since she had left with no sign of her return. Finally, the garage door opened again. I also heard another car pull into the driveway. I heard her talking to someone - there must be someone else with her.

She called for me to come downstairs reminding me that better still be wearing her things. I fixed the wig in the mirror, slipped on the shoes, arranged the skirt and blouse, and maneuvered the stairs. She was standing by the fireplace and obviously had her hair done. It was very different and very sexy. I knew this was a tease for me and I was so afraid it would make me hard again. When I got into the family room, she called to someone who I could not see. Her comment was, “Well, what do you think?” Two guys came out from the kitchen, and I recognized them from the salon. They both whistled catcalls at me. I was so humiliated and embarrassed. All I could do was stand there.

She told me that since I wanted to wear her things to look like a woman, she thought she would give me the opportunity to actually experience womanhood. While she was having her hair done, she told them about what she had caught me doing. Together, they came up with this plan to introduce me to the sisterhood.

My wife pushed me to my knees in front of one of them. As I awkwardly kneeled in those mules, she told me to take out his cock and give him a BJ. I was warned that I better do it right and quickly. I was shaking and totally embarrassed. I had never done this and wasn’t even sure I could. As I hesitated to even touch him, I discovered she had brought a small stick in with her from the yard. She hit me on my bottom until I complied with her wishes. As I looked up to find the guy’s fly, I discovered the other one was taking a video of everything that was happening.

I was able to easily get the guy’s cock out and into my mouth. I had my hand on his shaft and stroked it while I rubbed his pecker head with my tongue. He was responding to me, and I could feel him getting harder and harder in my mouth - he was flexing and responding. Then I felt him start to throb, so I knew what was about to happen – my mouth was filled with warm cum. He immediately put his hands on my head holding me while he pumped so much cream into my mouth. I didn’t know what to do with it, so I sealed his moving shaft with my lips and swallowed – over and over until the throbbing stopped. When he was done, he said to my wife that her sissy husband was a very good cock sucker and pushed me away roughly.

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I started to get up, but my wife stopped me with a tap of the stick saying, "You are not done yet."

Now, she pushed me down to my hands and knees. She lifted my skirt to discover I was not wearing anything under it and hit my butt several times with the stick. The other guy had removed his pants and shorts. He moved to my head and ordered me to make his cock good and wet. I obeyed taking his cock into my mouth. I felt him getting very hard.

He withdrew and went around behind me. I felt him separate my cheeks for my wife to spit into my anus. I was even more embarrassed now, but I didn’t have time to think about it as he forced his cock into my virgin anus. There was no gentleness in his actions at this point. He pushed all the way into my body until I felt him against my legs and bottom.

At this point, he placed his hands on my hips to hold me still as he began to fuck me – in and out, over and over. It seemed like this would never stop. To my own surprise and horror, I started to respond to his thrusts - I wanted this. Finally, throbbing began. I could feel him cum – my body was filled. He withdrew.

My wife slapped me with the stick to punish me for being "such an easy whore."

My eyes were closed, I was crying. My wife seeing his cream leaking from my body, took a tampon from her purse and inserted it into my anus. She then moved to the couch. I watched her remove her panties, lay back with her legs apart, and beg the guys to fuck her. When they were done, I was brought over to clean her pussy with my tongue.

At that point, the guys left. I was told to remain dressed. For the rest of the evening, I was her sissy. At various points, I was ordered to eat her to an orgasm. At first, she was slow, and she cried some. Eventually, she got her emotions under control and would cum quickly. Finally, I was given one of her nightgowns and ordered to sleep alone.

In the morning, I woke and got dressed for work. As I was leaving, she stopped me in the kitchen. She was watching the videos of me sucking the cock and them my virgin fucking. She said that she had not decided what to do with me yet, but I was hers. I would be her sissy slave.

When I came home that night, I dressed in the same outfit and wig. She said she would never wear any of those things again.

That evening after I had fixed dinner and was cleaning up, someone rang the doorbell. I was of course still dressed. I heard voices and recognized a couple of guys from her office. I was told to stay in the kitchen until called. They went up to the bedroom. I could hear the movement and knew they were having sex.

At some point, I was called upstairs and told to lick the cum from her pussy. She referred to me as her “cum bag”. I was told to leave but was called back again later to clean her out. This time I was also ordered to clean off each of their cocks.

For the next week, the evenings were all the same. I would come home, get dressed and cook dinner. During dinner, I was continually insulted. The doorbell would ring, and she would take her guests to the bedroom. I was called to either lick out her pussy or to suck a cock.

Finally, on Saturday morning, she packed her things and left. It has now been over two months and I have neither seen nor talked to her.

In the mail, I received a letter from her lawyer with divorce papers. I signed the papers giving her everything and moved to a cheap apartment.

Then, in the evenings, one of both of the original two guys, both hair stylists, came to my door. After the first visit, I knew to dress and be ready for them. Each visit started with them giving me pills. They taught me how to style the wig and wear makeup. Sometimes they would style it femme, so I did not have to wear the wig. I was expected to go shopping and buy different outfits to wear during their visit.

It was becoming more and more difficult for me to maintain my job. With the things I was expected to do to prepare for their visit, it was hard to hide things as a guy at work. On a Friday night, they showed up with their salon kits. This had not happened before. I was told that they were going to do my hair. Actually, I was happy about it because I was looking very rough without a haircut in over six months. Of course, I had no say in what they would do. It was colored several times. My natural dark hair was now quite light and many different shades. I learned I was now a blond with highlights and lowlights. It was cut into a spikey pixie style - very trendy. They also pierced my ears.

They spent the night. Apparently, they were very pleased with my new look. I got no sleep - one or the other of them wanted either a BJ or to fuck while the other slept. Saturday morning, we all went out to breakfast followed by a visit to their salon. That's when they told me that starting Monday, I would be quitting my job and coming to work for them at the salon. They gave me a couple of black skirts with white blouses - the shop uniform. I would start as their shampoo girl and would immediately be apprenticing to become a licensed stylist. I was in such shock that I couldn't say a single word.

It has now been almost a year. My name is now Gail. The pills I was taking were hormones. My boobies have grown, and my cock has shrunk and is always in a chastity cage. I always wear femme clothing and my makeup, nails and hair are salon done every day. I am a licensed stylist and have a following. Even with all these changes, I don't know where my life is going. Although the guys don't know it, I own the salon we all work in; but still, I am their whore.

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Written by Mitzie
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