A New Sissy ISO

I remember it like it was yesterday. As a matter of fact, it was only 6 months ago.

I'd been left by my second wife. Her major complaint was that I was not an attentive lover which is something she needs. Her second complaint was that I spent too much time reading erotic stories and masturbating.

On her first issue, she was right. I had lost interest in having sex with her. Maybe it was because she just lay there and acted like it was some sort of sacrifice for her to give up some pussy. She may as well have been watching TV or reading a magazine while I spent my energy and three long minutes humping away until I came.

What she didn't understand was that I had for all intent and purposes, checked out of our sex life together. She was not what I wanted. I loved her. Still do. But something deep inside me was bubbling to the surface.

That brings me to her second problem with me.

She was spot on. I was reading erotic stories and masturbating. What she didn't know, or at least I think she didn't know was that I was reading stories about submissive males. Males who were lost. Not gay, but neither were they completely heterosexual. These males were trapped in between those two worlds and as a result, they were pretty much at the mercy of real men and cruel women.

I like to think of them, us really, as gentle souls or soft boys. In reality, society has another term for those like us. To the rest of the world, we're known as sissies.

For no other reason, we're labeled. Sissy. The word has many negative connotations. To the outside world, we are freaks, something to be looked down upon. I accept their opinions. I accept them but do not share them.

Most of the sissies I read about are caring, loving souls who wish nothing more than to please their partner and whomever their partner may share them with. You see? Sissies mean no harm. They do not force themselves on anyone. They aren't on some street corner espousing their way of life as the way everyone should live.

My reading gave me an understanding of exactly what a sissy is. That reading gave me more. At first, I was amused when reading how sissies are less than real men. I entertained myself reading about how the sissy feminized themselves or were forced by a real man.

I used to skim over the parts where they sucked cocks or gave up their boy-pussies.

Funny thing about reading too many stories and articles. Empathy became arousal. And that arousal gave me clarity. I started to try to identify with them.

I already knew that as a lover, I fell short of the mark. Pussy didn't hold for me the allure it once had. But, before you suggest that I run out and join a pride parade, I was not interested in men, per se. Not like that.

I found myself exploring my submissive persona. That wasn't a difficult task. Under all my pervious teen aged bluster, I had since I reached the age of consent, been what some might call meek or compliant.

A little background on me. By the time my second wife left me I was 30. 30 and going nowhere. I'm not a big male. More to the point, I'm average, or I think I am anyway. All my life the women in my family have told me I was cute. Even in school the girls would tell me the same thing. "Oh, johnnie, you're so cute."

As those sissy stories began to have an effect on me, i took stock of myself.

At 5', 6". with slightly flared hips, shapely though nearly hairless legs, arms and chest, I hardly looked the part of the truly masculine man.

Appearing younger than my thirty years, my wide blue eyes and a spray of freckles across my button nose gives me a mischievous look; you know the look, the one that makes the ladies tell me I'm cute. To be honest, I looked very similar to a Tomboy.

I did not nor do I resent the way I look. I mean, how useless would that be? Instead, after my marriage imploded just weeks short of our second anniversary, I delved into my sissy fantasy.

I was drawn to those web sites that displayed graphic images of sissies and real men having sex. Well, it was more like the men were using the sissy for their pleasure rather than the sissy being an equal partner.

One photo struck a chord deep within me and whether it altered my psyche or just made me see myself for the first time, I knew I wanted to experience what I'd seen on those sites. That photo was very explicit. A pretty boy on his back. His head turned to accept the cock he was being fed. A large fat, cock was lodged in his pussy. God help me but I masturbated so many times to that image I lost count.

Then, one day it occurred to me that rather than continuing my fantasy, perhaps it was time for me to experiment; to see whether that lifestyle was in fact, for me.

Where to find such an experience? Where to look for the perfect man to train me?

I decided to place and In Search Of, (ISO) online at a few of those adult matching sites. I spent a pretty penny to place those ads.

Specifically, because I know you are curious about my ad, I asked for "a strong-willed man to teach me the values inherent in a gentle soul. I desire training to be the ideal sissy." Mind you, I had no preferences for anything other than a man sincere in his response.

Yeah, I know. Too on the nose, right? I had morning after regrets for having placed such an ad but, in for a penny as they say.

It wasn't long before responses arrived in my mail box.

I weeded through many, thanking them for their interest and then deleting those I felt were not what I was looking for. You know what I'm talking about. Those responses that said stuff like, "I'll make you the best cock sucker this side of Cleavland, Ohio." or, "I'll pound that fat ass until you cry uncle."

I needed more than that.

I sorted through the remaining responses, categorizing them into those who showed the most promise and those who were close.

I replied to one asking if he was experienced in dealing with newbies like me. Assuring me that he was, I agreed to meet him in a small cafe in town.

I waited at the agreed upon location and much to my dismay, he failed to show up. That was when I learned that there are those who, like me but on the other side of the coin, that wanted to taste the eroticism of training a sissy but lacked the boldness to overcome their fears to try something new.

It was either that or some near retirement aged dude, sitting in front of his computer, his gut hanging over the waistband of his thread bare boxer shorts, his 4" dick poking through the fly frantically masturbating as his wife slept in front of the TV.

Whatever they were, I found out quickly that there are a lot of insincere people out there.

When I finally met a man who I felt might be just what I was looking for, we sat and ate lunch as he asked me tons of questions while at the same time assuring me that he would be gentle.

To be honest with you, while I appreciated the gentleness he portrayed, he was not what I wanted. I needed a take charge man. A man who knew what he wanted and exactly what I needed to be all that I could be.

I met several of the same sort and felt that my search might be in vain. So, unfortunately, I was back to reading, looking, and masturbating to what was on my favorite web sites.

Thinking that I might be too specific, too choosey, I decided to contact one of those I originally found to be lacking.

The first time I found myself over a man's lap being spanked and then told to suck his cock was uninspiring. I could tell he wasn't into what he was doing. He was either too nice or too inexperienced.

I had a couple near so-called adventures like that and was about to give up.

Then, out of the blue I received a response from a man who promised me that he had exactly what I was looking for. Instead of he and I agreeing to meet some place, he insisted on setting the time and place. To quote him, "If I tell you to be there at 1 PM, sissy, you make sure to be there at 12:30 waiting for your man."

Now that was what I had in mind. A take charge man. Aggressive yet not seemingly dangerous. Expecting his instructions to be followed without delay or complaint. It sounded promising. It was an Instant erection causing response.

It's was what he said, "If I say be there at 1, you be there early." that made my dick throb.

"How will I know you? I asked when he set the meet.

"Don't worry about me, bitch. I'll know you when I see you."

You know how you just know?

I had my long hair brushed 100 times and debated whether to apply a touch of mascara before deciding not to be so over the top at our first meeting.

Like the man said, I was there at 12:30 precisely. I fidgeted while I waited. Every time the restaurant door would open, I would look up hopefully only to be disappointed.

So, wait I did. He kept me waiting until 1:45 and just as I was about to leave, a man rose from the table three up from mine and approached me. "Good for you, bitch. I see you know how to obey a man."

"Yes, sir," was my surprised answer.

He sat across from me, his dark brown eyes piercing through mine. He took my hand in his and turned it over, inspecting it for some reason. "Nice soft hands of a bitch," he grinned. "I like my bitches to have soft hands."

My spine tingled in a nice way. "Thank you, sir."

He asked me several questions, gauging my sincerity I supposed. When I told him what I was looking for, his answer said it all.

""Who the fuck said you have a choice, bitch? I'm claiming your faggot ass here and now."

Taking my wrist, he led me to the cash register and told the matron that I'd be paying for both lunches.

Then, and not against my will, this big strong Black man led me out of the restaurant and down the street. He wasn't dragging me; he didn't have to. But I struggled to keep up with his long stride and quick pace.

My heart was pounding a mile a minute when he led me into a hotel. With one arm around me, his big hand on my bottom, he said not a word until we got off the elevator. Handing the key card to me, he walked in as I opened the door. I followed him into his room, and waited for his instructions.

He sat in one of those hotel side chairs. To me, he looked as though he was sitting on a throne surveying his kingdom. Regal, handsome, his dark eyes showed neither menace nor emotion.

I stood perfectly still as he appraised me.

"Then, after several minutes of silence he asked me what I could do for him.

"Um, sir, I'm sort of new at this but...."

"Shut the fuck up," he said. You reading this need to understand that he didn't say that in a threatening way. Nor was it said in anger. It was simply, "Shut the fuck up," which I did.

He told me to strip which I did, hurrying out of my clothing.

He pointed to my dick and chuckled. "Just like a sissy to have a little dick."

What happened next was most embarrassing. Hearing him ridicule my privates made my dick get hard.

He had me pose in all sorts of degrading positions which only fueled my arousal.

He wanted to know if I was married, if I lived alone, if I was employed, and how much did I make. He asked pointedly if I was gay.

He asked why on my profile did I not say I was specifically looking for a Black man?

"Sir, race was not important to me. Really, never has been. I was looking for a man to take charge. A man who would teach me how to please him. A man to train me, correct my deficiencies, and help me be the sissy I think I was meant to be."

He waited for me to tell him more.

"That you're a Balck man is incidental, sir. I mean incidental to this relationship. That you are a large, handsome man who readily took charge of me, is not incidental but encouraging, at least to me anyway."

"Ever sucked a cock?"

"Only one, sir."

"When?"

"Um, it was one of those guys who responded to my profile, sir."

"White or Black?"

"Sir?"

"The cock. Was it white or Black?"

"White, sir."

"So you've never sucked a Black cock, then?"

"No sir."

"Do you want to suck mine?"

His question caught me off guard. "I uh, well, um, yes sir, I mean if you want me to."

"You'll have to earn that privilege, sissy boy."

And there it was. I was accepted as a sissy already and that made me smile. "Yes, sir," I smiled. "Thank you, sir."

He saw my reaction and chuckled. "All you sissies are alike," he said.

He made me feel as though he knew all there is to know about training a new sissy.

"Give me your phone number, bitch."

I gave him my number to which he explained that I will never know his number. "You be ready to answer your phone, day or night, faggot. Never let it go to voice mail on me."

"Yes, sir. I promise to alw......."

"Shut the fuck up. Get dressed and get the fuck out of here. I'll let you know if I intend to retain my claim on your sorry ass. In the meantime, keep your phone handy and do not, I repeat, do not meet with any other man wanting to claim your faggot ass. For the time being, your ass belongs to me.

I dressed in a hurry and left feeling diminished, marginalized.

It was exactly how I hoped I would feel having a strong-willed man take control of me.

I went home and paused my online accounts. I wasn't sure if I should since he hadn't given me permission to jack off, but masturbate, I did. Three times that night as I waited for a call that might never come. "If it does come," I thought hopefully, "I'll get it the first ring."

I drifted off to sleep imaging being owned by that handsome man who had never told me his name.

Part 2 coming. Comments are appreciated and emails answered.