Escort for CD (part 1)
I enjoy dating CDs and have for many years, but it's a hassle finding dates, until I became an escort. Enjoy this work of fiction.
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I'm Bill, age 35 and a lover of CDs. I suppose I'm gay, but I'm not really attracted to men, but love femininity – just not women. I'm sure that sounds pretty weird, but I've found CDs to be the perfect match for me. I love their feminine nature and how much they appreciate my treating them as a lady. They also really know how to pleasure a man – and could teach women a thing or two.
CDs tend to be cautious, and for good reason. They are especially vulnerable, since they fear exposure. Most men would rather be "outed" as gay than as a crossdresser. Sadly, some abusive men take advantage of their fear, knowing that they can rape or molest a CD and usually get away with it.
As a result, I usually have to win their trust before they would even agree to meet. I always tried to make it easy and safe for them, typically offering to meet them in a public place, such as a coffee shop. Often I would agree to meet them in boy mode as well, since many CDs don't feel comfortable going out dressed.
All this takes time, and it would sometimes take a couple of months to arrange a first date. That was starting to bother me, and I needed to come up with a creative way to date CDs.
I knew of a CD support group nearby and sent an email to Lisa, the group moderator saying, "I am a sincere man who enjoys the company of CDs, and want to offer them a safe date with a free escort. I want only to show them a good time and enjoy their company – with no strings."
I included my phone number in case she chose to call, and I was delighted to hear from her in less than an hour. We talked briefly and she invited me to her place for lunch. I quickly accepted and said goodbye.
On my way to Lisa's I purchased some flowers. I arrived and Lisa greeted me. She was conservatively dressed, wearing a pink blouse and a red skirt, and 3" maroon heels. Her hair was auburn and she appeared to be in her early 50's, though I'm not very good as estimating ages.
Smiling as she took the flowers from me she said, "Well Bill, you are off to a good start."
Lisa had prepared a light lunch and we sat down to eat. She asked me many questions and finally appeared satisfied of my intentions. "You are quite different from the usual men that girls like me meet," she said.
I knew that was true, but wanted to know her take on me, and asked, "In what way?"
"Most men see girls like us as easy, and think we are good for a blowjob or quick lay," she explained, "but you are really willing to pleasure without reciprocation?"
"Yes," I agreed, "no strings – just a nice date."
"What do you get out of it?" Lisa asked, "what about your needs?"
"Well, I will have an enjoyable visit, and hopefully a second date," I returned, "and I'll take care of myself later."
"So you are willing to do all that for a jackoff memory?" she asked.
"Crudely put," I agreed, "but true enough."
"If you are successful there could be many girls dating you," Lisa warned, "it could get expensive."
"I am a free escort," I replied, "but I don't have a lot of money, so I will need the girl to cover the cost of the date – I'll cover the gas cost, though."
"For what you provide," said Lisa, "I'm sure most girls would be happy to treat you. Do you have any requirements for the girls?"
"Not many," I replied, "Only that they be femme, but not necessarily fully passable, but no bearded ladies or hairy men in dresses."
"So would I qualify?" Lisa asked.
"Without a doubt!" I answered.
Lisa took my hand and led me to the couch, where we embraced and kissed. She was definitely trying me out, and I enjoyed every moment of it. After about ten minutes Lisa said, "I think I'm ready for more."
"What did you have in mind?" I asked.
Lisa stood up and reached under her skirt, and slipped off her panties. "I'd like to enjoy some of those oral pleasures you mentioned," she said.
I was eager to lift Lisa's skirt and enjoy her charms, but first asked, "Front or back?"
"How about both?" responded Lisa.
I positioned Lisa kneeling on the couch, facing the back. I knelt on the floor behind her and raised Lisa's skirt, revealing her soft round buns. I spread her cheeks and pressed my lips to her rosebud. She moaned with pleasure and I extended my tongue into her. Lisa pressed back against my face, as if trying to drive me deeper. I responded as well as I could, wishing my tongue was longer.
I reached between her legs and took her clitty into my hand, already thoroughly aroused. After gently stroking her, Lisa said, "You better take care of that!"
I pulled back and Lisa turned around and sat on the couch, lifting the front of her skirt up. I took her into my mouth, sucking gently and soon she pumped her hot load into my mouth. I welcomed the familiar taste and held her in my mouth until her climax finished.
As I looked up at Lisa's smile I felt a sense of accomplishment in taking Lisa this far. "Can I do anything for you?" she asked.
"No need," I replied, "unless you really want to."
"I do," Lisa said, "but I'll save that for our second date."
"I'd like a second date with you," I said.
"We have a meeting of our group here next Wednesday at 7pm – you should be here and I'll introduce you to some of our girls."
I agreed and we kissed as I departed. When I got home I immediately jacked off, thrilled with my date with Lisa!
–––––––––––––––––––– To be continued ...
Feel free to contact me with your comments or requests. –Bill (oral_guy_2000@yahoo.com)
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