Small Cock Frustration Pt. 02

Story Info
Jim becomes Janet and finds new meaning to life.
3.2k words
4.59
21.2k
16

Part 2 of the 6 part series

Updated 06/09/2023
Created 09/24/2019
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
jamtby
jamtby
297 Followers

Despite the relatively short distance to my home from Mistress Alexa's club, it seemed like it took hours to get home. The bulge in my pants demanded release but remained restrained in my new panties. It felt strange but all I wanted to do was get out of my clothes. Finally, after what seemed like hours, I arrived home. Once inside I stripped off everything except the panties Mistress ordered me to wear.

Being naked is a wonderful feeling especially when you are sexually excited. Moving to the bedroom I had to admire my panties in the full-length mirror mounted on the closet door. While I did not see myself as a beautiful woman, the increasingly feminine look that I seem to be achieving pleased me. My breasts seemed a bit larger and firmer. My ass a bit softer. I was seeing myself change after only a few hours with Mistress Alexa.

Finally, removing the panties, my small, insignificant cock appeared. Buried in the course hair of my bush, it seemed smaller. Suddenly a wave of doubt washed over me. "How could anyone respect someone with such a small useless cock?"

Mistress asked me to check around the house to see if there were any toys or other indications as to my wife's sexual interest. Carefully searching through the dresser drawers used by Carla, I found nothing. Several pairs of thong panties were found in the back of on drawer. I had never she her wear them. Continuing my search, I checked the master bedroom closet, nothing out of the usual was found. One pair of 5-inch high heels were new, but I had never seen her wear them. About ready to conclude Carla was not hiding anything, I decided to check one room I seldom enter, her office. A grey storage cabinet behind her desk was locked. Being curious I wanted to see inside. Why would Carla lock her storage cabinet? I started to search for a key. After 20 unsuccessful minute searching, I was ready to give up. Ready to leave I noticed something small on the top door molding. Pure luck provided me the key to the cabinet.

Opening the cabinet, I found the usual office supplies on the bottom two shelves. The top shelf had a significant surprise. It contained several black lingerie items, a leather corset, and some pictures. These were not pictures of the girls visiting a restaurant or museums. The first one that caught my attention was Carla wearing a strap-on penetrating a nude woman. Other pictures showed similar scenes with different women. The final picture was the most shocking for me. There was my wife, naked, on all-fours being fucked by a big woman. Devastated, I carefully replaced the pictures, locked the cabinet and returned the key its hiding place.

Angry and swearing I spent 15 minutes coming down. Now more dedicated to the adventure with Mistress Alexa, I followed her instructions. Jumping into the shower a razor and shaving cream, I started removing all my body hair. The under arms and legs were very easy. The moment of truth came when I had to shave my pubic hair and balls. That required greater care than other body parts. As I watched the shaving cream and hair flow to the shower floor and drain, I felt increasingly submissive. How would I explain to anyone why I had shaved my pubic hair? After admiring my new, nude look in the mirror, I got in bed.

As the morning light streamed over the top of the bedroom drapes, I awoke. A quick shower, a shave, and getting dressed, I grabbed a quick cup of coffee. The car started and I was on my way to Mistress Alexa's club. A Dunkin Donut along the way provided another coffee and a donut. I arrived at the club about 8:45. The front door was unlocked and a note indicated I should go in and prepare for Mistress at 9:00. At five minutes to 9 I stripped off all my clothes except the panties and proceeded to the white line.

At 9:00 I heard someone entering the room. A hand on my right shoulder and warm breath on my neck let me know Mistress was present.

"Very good Jim, you are obeying my orders. That is very good. The panties look fantastic on you."

Shaking my head, I said, "Thank you Mistress"

Her next action was to pull the panties down and told me to step out of them.

"You look very good." Her hands slowly stroked my back, ass, and legs before moving to look me in eye. Moving down my chest, she stopped to feel my cock and balls.

"You did very well. You are smooth and soft. You followed my instructions well. I told you that I would shave your ass, so you look like a soft woman. That is next."

Grabbing my cock, she said, "Follow me and lay face down on the massage table."

Getting on the table and laying on my stomach as ordered, I felt embarrassed. What was she going to do? Within a minute I felt a warm, wet cloth being run up and down my crack. Then the cream was applied. Finally, the razor started its work. Any pretense of masculinity was being removed. I soon felt totally naked and very submissive.

"Now you really look good. You are very fem looking right now. I love your smooth body and firm boobs."

Still on my stomach I said, "Mistress, I feel very naked and vulnerable."

She simply said, "Yes, I know and you are a true submissive. You are going to receive a butt plug to stretch you out. You will keep it inside until I give you permission to remove it. Is that clear?"

Nervously I said, "Yes, Mistress."

Within a minute I felt a lube on my anus and then pressure. It hurt at first but after is was pushed totally inside, it strange and perhaps erotic feeling took over.

"Get off the table", was her next order. Sliding off the table the butt plug felt strange.

"You no longer have a cock Jim; you now have clit and I own it Do you understand?"

Shaking my head yes, I was getting aroused.

"Good. Now we need to give you a proper name. Jim is not a feminine name. When you are with me you will be Janet. Do you accept that name?"

As the arousal was gaining strength, I only shook my head in affirmative and said, "Yes, Mistress"

Once again, she grabbed my cock--I mean clit and led me into her office. Ordering me to sit facing the wide screen TV.

"Yesterday I asked you to look into your wife's private life. What did you find?"

After hesitating and getting emotional I replied. "Searching the bedroom, closets and in all the usual places, I found nothing. Finally, I went into her office where she has a metal storage cabinet. It was locked but only through luck I found the key hidden over the door. I found things I never expected and worse it destroyed me emotionally."

Looking very sympathetic and concerned she said, "Please continue."

"There were thong panties, black corset, and most hurtful were pictures."

"Pictures? What type of pictures?" she asked.

"They really deflated my ego and made me feel very insignificant. There was my wife wearing a strap-on fucking a nude woman. There were other pictures of her fucking other women. The final picture was a Carla on all fours being fucked by a large, tough looking woman. It destroyed me."

"I see your wife is a lesbian then. How does that make you feel?"

I replied, "Hurt, angry, and emotionally drained. To see my wife being fucked by this big bitch made me both scream and jealous."

"That is understandable. Your wife is a lesbian and apparently enjoys both dominating and being dominated. I wonder if she is a sub of the woman who fucked her. But clearly she is a lesbian."

"I think she still loves me at least a little. What have I done to hurt you?"

"Listen to me, you did nothing. You wife has had an interest in other women. I suspect this goes back to a much earlier time in life. How long have you known her?"

"I have known her since our junior year in college. Why?"

"I am only going to make a guess, but I suspect her interests in women occurred long before she met you. Who did she hang out with in college?"

Responding, "I don't really remember but she was a member of a sorority which seemed to have a lot of girl only parties. I was invited to several parties with other men."

The thoughtful look on Mistress' face indicated she was thinking. "I can not say for certain without spending some time with her, but your wife probably had an interest in women at an early age. When you and she got married, you provided her cover for lesbian activities while looking like a family woman. You have been a meal ticket and provided respectability."

She continued, "The woman who fuck your wife, can you give me a better description?"

I said, "Not really she was big. Her buzzed hair cut made her look more like a man than a woman. She appeared to have Carla fully under her control. But who knows base on one color picture? It did seem strange that someone was taking pictures of her in that position."

Mistress replied, "Not necessarily. I can only speculate but I would guess on one outing with the girls your wife met the woman who seduced her and made her into her submissive. That woman then used your wife to recruit other women into their group. This could either be a very willing relationship or one based upon black mail. Again, without talking to her , I can only guess."

The look on my face communicated total frustration that I had been working to support her extra marital affairs.

Mistress then said, "Let's not talk about your wife but rather how you can become a happy person. Before we go further, I want you to suck on this."

At that she stuck a larger butt plug into my mouth. After a minute she had me standup. Removing the original plug, the larger one replaced it. The initial pain quickly faded and again I sat down as a strange arousal continued.

"Janet, your new pussy is being stretched to make it more receptive for future activity. Now watch the video."

As the screen came to life, I was shocked to see myself standing naked in the hall.

Mistress said, "I took this video this morning as you were standing waiting for me. You looked very exciting to me. You will want to watch the rest of the video and at the end tell me what you think."

The video stayed on me for about a minute then changed. A naked male was standing in the hall next to the massage table I had been on only several minutes before. At that point another naked male came in and ordered the first male to bend over the table. After playing with his cock and balls, the second man proceeded to penetrate the ass of the male who started to moan and became very excited and the man then fucked him and stroked his cock. The male started to beg, "Fuck me, fuck me." Suddenly the male erupted while moaning in pleasure.

Watching this made me feel aroused and my clit got hard. Mistress noticed I was excited.

The video changes to another naked male standing in the same place as the first. A naked woman wearing a strap-on entered. Taking control, she ordered the male to bend over. After a minute on rubbing his back and butt, she made him kneel and suck her strap-on. After a minute he reassumed the position and she penetrated him. Again, the male started to moan. The woman screamed "You need to be fucked faggot. I am going to make you my bitch." As he moaned and cried, she kept him on the edge than an eruption caused him to collapse climaxing.

This made me very horny and again stiff. I could only imagine Carla fucking me. I started to need to relieve the pressure building.

The next video again featured a naked male. This time a shemale entered the picture. Within a minute she had the male on his knees sucking her cock. This lasted until she erupted in the male's mouth. As he tried to spit out the cum, she pulled him to his feet, bent him over and proceeded to fuck him. How she recovered to quickly amazed me. As he moaned and begged her to fuck him, I became increasingly aroused.

After he climaxed, the video immediately changed. An attractive nude woman was now standing where the males had previously stood. A naked male entered picture and took control of her forcing her to her knees. Pulling her head to his erect cock, she started to suck. That finished the video at that moment.

Looking at me with a knowing look Mistress asked me, "Janet which one of those scenes excited you and who would you want to be of those cases.?"

Stunned at the question I couldn't immediately respond. The best I could do was say, "uhm...ahaaaa...uhm."

With a smirk she said, "I was watching you and more importantly watching your clit. While each scene excited you, the two that got you totally aroused were the women using the strap-on and the shemale. I could see your respiration and your skin turned red. Given you small clit, I suspect you wanted to be on the receiving end. Am I right?"

After another moment I responded, "Mistress, you seem to read my mind and know my inner fantasies. I would love to be the one receiving from the shemale. It is not clear why she is the most exciting, but she is. I must be a pervert."

"Yes, I know you and you are not a pervert. You have desires and needs that are not strange or wrong. You need to be who you are. Let me ask you. When the woman with the strap-on was fucking the male, did you think of your wife fucking you?

"Yes, I did. The picture of her being fucked by that bitch also is stuck in my head."

"Don't worry about your wife. My concern is you. I am going to take you to the next step. It is time for you to be properly initiated. To do that I want you to go into the hall and face the massage table. But before you leave my office, I want to pull that butt plug out of you. I want you to be totally free and uninhibited. Moan, cry, scream, or whatever you feel. You need to let go of tension and old thinking."

I stood up and Mistress removed the plug. The sudden departure of that device felt both a relief and arousing.

Entering the hall and facing the massage table I waited for what was to happen. I stood there for almost 10 minutes and nothing. Finally, I heard someone approaching me. This person was either bare foot or wearing shoes that did not make a sound on the bare concrete floor. A warm hand touched my right shoulder and it began.

"Janet, I am going to make you a very happy gurl. You are mine and I am going to make you feel wonderful". With that the person started to rub my back in a very erotic way. Slowly as she worked down my back, I began to feel more aroused.

"Spread your legs was ordered" Reaching between my legs the person (wasn't certain whether they were male of female) reached for my cock and started to play with it. They knew how to excite me. I started to moan as pleasure built. They continued massaging my balls and it became increasingly difficult to control myself. Suddenly, I felt something hard pressing against my anus. Continued to stroke and rub my cock and balls, a sudden thrust and my anus opened, and the person was in me. At first, they only pushed in and slowly pulled back. Then she said, "I am going to fuck you like you have never been fucked and make you my bitch."

Faster and faster the pumping continued. and I was moaning and begging for more. Reaching a peak, I lost control. "Fuck me harder, fuck me harder." Then like an earthquake I exploded. I screamed in ecstasy and then collapsed.

I finally turned around to see who had taken me to this point. I was surprised, it was Mistress Alexa standing before me wearing a black corset and a strap-on. She smiled.

"You were wonderful" she said to me. "You are mine. The next time there will be a new experience".

"Now it is time for you to get dressed. Here are you new clothes." She handed me a bra, panties, thigh highs, 3-inch heels, a skirt, blouse, and a wig.

I was shocked but with her help I put on the panties and bra. She provided instruction of putting on nylons and heels. The brunette, shoulder length wig looked very good especially after Mistress smoothed it out with a comb. Finally, the skirt and blouse.

"You look very lovely."

I was very uncertain about how I looked. She expected me to go home dressed like this.

"Mistress, I don't know if I can go out looking like this. I can hardly walk in these heels and let alone drive. If my wife comes home before I get there, she will be shocked and start a fight."

She simply smiled, "You look great. My biggest concern is that guys will be hitting on you. If your wife is home, she may want to fuck you like she does all her girl-friends." Her laugh helped put me at ease.

"I want you to wear these clothes as much as possible. Yes, you must go out and go to work, but when you are home and your wife is not there, wear these. You really look fantastic. Next time I will work on make-up. I will have other surprises. I want to see you here again next Monday. Wear these clothes and go to the white line dressed and wait."

Very self-conscience I slowly walked out the club and then quickly into my car. The trip home was without a delay. Pulling into the garage I breathed a sigh of relief; Carla was not home. I got out of the car and quickly moved to the Master bedroom. I stopped for a moment in front of the floor length mirror to look at myself. Surprise, I didn't look to bad.

I quickly stripped off the clothes. Folding them they were placed in a plastic bag and then locked in the truck of my car. Still naked I took one more look at myself and decided I liked what I was seeing.

To be continued...

jamtby
jamtby
297 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
3 Comments
jamtbyjamtbyover 1 year agoAuthor

Thanks for your comment regarding this story.

Shaglus_ZieglerShaglus_Zieglerover 1 year ago

Better than the first.

AnonymousAnonymousover 4 years ago

time to confront his wife about her infidelity

Share this Story

READ MORE OF THIS SERIES

Similar Stories

"Sissified": 12 Days of Sissy-mas Straight man is turned into a submissive sissy by...in Transgender & Crossdressers
The Deal Freddy's wife convinces him to dress up and go clubbing.in Transgender & Crossdressers
Hypnosissy 01: Becoming a Cocksucker Straight guy watches porn tapes that are not what they seem.in Fetish
Shemale Surprise A married man is seduced and taken by a friend of his wife's.in Transgender & Crossdressers
A Slut is Born Young man forced to be a womanin Transgender & Crossdressers
More Stories