Small Cock Frustration

“Notice his breasts. Yes, they are small, but he has them. Touching them made them hard. Much like yours got hard when I touched them. I want you to touch your breasts and make them hard again.”

I slowly obeyed and as they were rubbed the nipples became hard and my arousal grew.

Smiling Mistress said, “That is very good Jim. From the look on your face and your body language I know you are getting aroused and that is good. It is okay for you to feel pleasure.”

The video flashes for a moment and where the male stood a female appeared. She was naked to her waist. Her breasts were small but firm. Her face looked somewhat familiar but was very attractive.

Mistress said, “Notice this person. She is attractive and has a beautiful look about her. Very nice firm breasts and nipples. Her shoulder length, brown hair framed her face beautifully. Are your nipples still hard?”

I simply replied and a short breathless way, “Yes Mistress.”

The girl on the screen turned around so all I could see was her back. Then the skirt she was wearing fell to the floor and she stood there naked.

Mistress asked me, “What do you see? Do you like what you see? Does it turn you on?”

No longer trying to be coy I said, “I see a beautiful woman with a very cute ass. Yes, it does turn me on.”

She asked, “Are you sure?”

“Yes, Mistress that is beautiful. If I had a cock that worked, I would want to fuck her.”

A few seconds later the woman turned around and surprise, she had a cock. It was small, like mine, but a smooth cock and balls.

“Now, do you recognize this person?”

I said, “No I don’t.”

Mistress said, “The male you saw at the beginning of this video is this woman. He became she. Within a minute you will see why he made that decision.”

The video now shows the male/female bent over a couch. A male enters the picture. He is also naked and has a large cock. Mounting the Shemale, he penetrates her ass and starts to fuck her. Unlike the earlier part of the video, this has sound. The Female can be heard moaning in pleasure and crying out “Fuck me baby. Fuck me please.” After several more minutes the female screams in pure pleasure as she shakes from a strong orgasm. Then the video ends.

“How does that make you feel?”

I tried to hide my arousal and sexual emotions but Mistress was having nothing of that.

“You are very excited, and wished you were the female and could be fucked like that. She has never had the sexual release and pleasure as a male that she has a female. You want that don’t you?”

Hesitating a minute, I could only shake my head yes.

Mistress smiled, “I know you want that, and you can have that. You see, his/her cock had nothing to do with sexual pleasure. It remained unchanged throughout the video. What changed was the confidence that sexual pleasure could be achieved.”

She continued, “Let me ask you have you ever been fucked?”

Embarrassed I finally said, “Once in college.”

Mistress ordered me, “Tell me about that time in college.”

“Okay----uhm----uhm. I had just finished my last exams before graduation. A group of us were celebrating in our favorite campus bar, Jimmy’s. The celebration continued but some of my friends still had exams, so they left to get back and study. Finally, a graduate assistant that had taught one of my classes the previous semester asked if he could join me. After a few minutes I had to excuse myself and take a piss. When I returned there was a fresh beer waiting for me. Greg, the grad assistant, and I talked for another 20 minutes or so then I started to feel dizzy. I couldn’t stand without feeling wobbly. Greg offered his apartment for me to rest. Once inside his apartment I flopped down on the couch. Within a minute I was un-ceremonially stripped naked, thrown on my stomach. With Vaseline being rubbed on my anus. Next thing I felt was something hard being pressed against my rectum which opened for Greg. He proceeded to fuck me. I don’t remember much except I felt pain and then an unfamiliar sense of pleasure. I passed out. The next morning, I woke up with a headache, naked, and wondering what happened. Finding my clothes, I got dressed and ran out the door. I later found a envelope with several polaroid snap shots of me lying naked with Greg fucking me. A note said, “I have some great 35mm pictures of you. Stop by so you can see them.”

Mistress said, “That had to be a terrible experience. I mean being treated that way. How did you feel?”

“I felt angry, ashamed, and abused. My ass tingled all day. The strange thing was that I had fantasies and had to masturbate several times that day. After that I blocked it out of my memory. Watching some gay porn brought that night back but it seemed more erotic than it did at the time.”

Looking deep into my eyes Mistress said, “Jim, you are a bisexual. Not a thing wrong with that. You need to accept yourself for who you are and not judge yourself harshly. I am going to make you proud and give you a new life. It will be for the best and you will find pleasure and fulfilment like you could only imagine.”

She continued. “I want you to go home. Do the following. First, shave all your body hair. You can either shave or get a hair removal cream. The one area of your body that will be hard to shave—your ass, I will do for you tomorrow. Either works. Second, I want you to buy moisturizer and rub it onto your entire body. Finally, I want you back here tomorrow at 9:00 AM. I expect you to be standing naked on the white line when I arrive. Are there any questions?”

Looking her in the eye, “No Mistress. I understand your orders. I am trusting you at this point and will be standing naked on the white line at 9 tomorrow.”

Smiling she said, “I am pleased. I know that you will be very happy once we are finished. There is one other thing. You indicated your wife is away for the weekend. I want you to check out and see what toys you can find that she might be using. If you are not having sex, she is doing something. Without meeting and talking to her I can only make a guess but I suspect she is a lesbian. That is why she spends so much time with her girl friends. The toys you find may help me to confirm or disprove what I suspect. She may have a male lover for all I know but I am certain you are not being treated well.”

We headed into the great hall I started to get dressed but before I put on my boxers Mistress stopped me and gave me a pair of women’s panties. “Wear these tonight and when you arrive tomorrow.”

As I started the drive home, I remained aroused. I wondered am I being a fool or is there a new day and perhaps life ahead. Nervous but excited I was committing to this new adventure.

To be continued.....