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.
