Planned Outings (part 12)
My sexual life has been very private – while many know I am a cocksucker, that part of my life is very separate from my family and business. Many times I have wished that I could be out to some of my closest associates, but could never take the chance. This story series was inspired by that desire. This is dedicated to my late friend Phil, who was out to everyone.
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I awoke, got ready for work and had breakfast. I waited a few minutes for Mark to arrive. Today he whipped out his cock while standing in the open doorway, so I blew him there with the door open. Nobody could see more than Mark's back standing there. As usual he came quickly and departed, so I left for work.
At work I found myself thinking about Kathy. If only she had a cock she would be perfect for me, but I was intensely attracted to her femininity. I called her and arranged to meet her for dinner at a local Italian restaurant.
With that arranged, I continued in my work day. My work proceeded and in mid afternoon I received a call from Jeff, wanting to stop my when I got home. I quickly agreed, always welcoming such an easy blowjob.
On my way home I received a call from Lee who said he had arranged for me to suck at the strip club glory hole tomorrow night from 7-8pm. I agreed and said I would meet him in his garage at 6:45pm.
After arriving home and changing clothes, I drove to the Italian restaurant and met with Kathy. It was really nice to see her and I was beginning to have feelings I didn't entirely understand.
"I find myself very attracted to you, Kathy," I said, "I'm not sure what to make of the feelings I have for you."
"That can be pretty tricky," she agreed, "in the past being with someone of the opposite gender was a relationship, and typically love was involved. But in a 'friends with benefits' situation, there is intimacy without obligation, which is a different nuance."
"I know that complicates things," I agreed, "but I find myself beginning to really care about you."
"Could you envision yourself falling in love with me?" Kathy asked, "would you be wanting to plan your future with me?"
"I don't know," I said, "but my feelings seem to be heading in that direction."
"I know that when you give a man a blowjob, you don't start to fall in love with him," she said, "how is this different from that?"
"I don't know," I said, "but it does seem different. When I have intimacy with you, it also seems to be coupled with emotional feelings about you."
"Well, perhaps it is a simply boy/girl thing," she said, "It's not unnatural, but I may not be the one for you.
"The last time you said there was a person you know who might really be right for me," I said, "what did you mean by that?"
"Perhaps a Tgirl would be perfect for you," she said, "I know one who would be interested in a serious relationship."
"I don't understand," I said, "exactly what is a Tgirl?"
"Tgirl means transgender," she explained, "born a man with the mind of a woman and living full time as a woman. They look and act fem, but many still have a dick, which I think you would like."
"So they are like cross-dressers," I said, "I have enjoyed being with them."
"Similar, but not quite the same," she explained, "cross-dressers are often men pretending to be women. For a Tgirl, she IS a woman, just with some male vestiges left over."
"I think I would be interested in such a woman," I said, "but I think I need to learn a bit more."
"Agreed," said Kathy, "I'll send you some web links that will explain more about Tgirls. I have a friend I can introduce you to when you are ready."
My head was reeling with the possibilities. A woman that was a woman in every important way, but still had a dick – that was amazing. I had enjoyed being with cross-dressers before, but someone who wasn't just playing "dress up" – that was really special!
"I think I would like that," I said, "but meanwhile I do have some special feeling toward you and really want to pleasure you."
Finishing dinner, we went back to Kathy's house, and I removed my trousers soon after I was in her door. Kathy excused herself and changed into her lingerie robe.
When she returned I took her in my arms and kissed her. "I look forward to spreading your cheeks again and kissing you deeply" I said.
She took me into the bedroom and asked me to lie on my back in her bed. I laid there as directed and she knelt over me, moving her ample ass to my mouth. She spread her cheeks as she lowered herself, moving her pucker directly to my mouth.
I enjoyed her warmth pressed to me, and extended my tongue into her hole. I reached around and felt for her clitoris, which I began to massage. Soon Kathy was cumming, pressing her ass harder against me. Then she leaned over and began to suck my cock. I kept my tongue in her the entire time she sucked me, and soon was cumming in her mouth.
She rolled off me and lay next to me, and we held each other closely.
She kissed me and I tasted my cum in her mouth. After a time we got up and got dressed. I drove back home, calling Jeff to tell him I was on the way.
Shortly after arriving home, Jeff came over and I took him into the garage. We went to the front of the garage, in front of my car and I dropped to my knees. "Here?", Jeff asked.
"Yes, of course," I said, "you cum very quickly and it will be done before anyone could notice. Besides it nobody can see what is happening here."
Jeff gave me his cock and I sucked him, bringing him to climax in short order. He zipped up and left.
I went inside and checked my emails. There was an email from Kathy with some links to Tgirl sites. Some were mainly pictures, which were really hot, while some gave information about Tgirls. One was a tutorial on dating Tgirls. I read them all with great interest. After awhile I notice how late it was and went to bed.
–––––––––––––––––––– To be continued ...
Feel free to contact me with your comments or requests. –Bill (oral_guy_2000@yahoo.com)
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