Best Friend CD (part 3)
A man discovers that his life-long best friend is a cross-dresser, and their friendship takes on a whole new meaning! I hope you enjoy this work of fiction.
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The next day at work I couldn't get Rachael off my mind. I hope she enjoyed our time together and that it wasn't too extreme for Ray. I valued my friendship with Ray, and knew that Rachael would change things, but hoped that I would not have to give up anything with Ray.
I didn't know how often Rachael would be around, and didn't want to pressure Ray about it, but hoped it would be often.
I little before lunch I received an unexpected call.
"Hello Marty," said Rachael.
"Rachael dear!" I replied, "this is a very nice surprise. I really enjoyed visiting with you."
"I enjoyed our time as well," she said, "and would love to see you soon. Are you available tonight?"
"Yes, I am," I replied, "I'd like to take you to a restaurant."
"I've never been out," Rachael confessed, "I'm not sure I would pass."
"Of course you will – 100%," I said, "I understand your being nervous about the first time, but I'll keep you safe."
"Okay," Rachael said, "Ray is trusting me with you, so I know I can depend upon you."
"Yes, you can," I said, "I'll pick you up at 6:30, okay?"
Rachael agreed and we hung up. The rest of the day I felt like a teenager on his first date!
That evening I picked Rachael up as planned and took her to a local seafood restaurant. I opened doors for Rachael and helped her with her chair. There was a middle aged woman who nudged her man and pointed to us. She probably was whispering "why don't you do that for me?"
If he was smart, he wouldn't tell the real reason – that I had a much hotter babe than he did!
"If you don't feel comfortable ordering for yourself, just tell me what you want and I'll order for you," I said.
Rachael said she would give it a try, and soon our orders were in.
I reached across the table and took Rachael's hands and said, "Rachael dear, I really like being with you, and would like to date you regularly, if that would be okay."
She smiled and said, "I would like that, but I'm not really all that sure of myself."
"I'm not all that sure of myself either," I confessed, "so we can figure this out together."
"You know I'm not like other girls, and as this progresses, you might feel uncomfortable with me."
"Rachael dear," I admit that I don't entirely know what I am getting into, but I am fully prepared to give you the attention a man should give his lady."
She smiled and squeezed my hand. Our meals arrived and we ate them, discussing the events of our day. After dinner we walked out to the car and I stopped and took her into my arms and kissed her. This time her mouth opened wide for me and we shared a passionate French kiss.
When we arrived at Rachael's she invited me in and we sat on the couch. We caressed and made out for a bit, and once again my hand slipped up Rachael's skirt. Her legs spread, inviting me to continue. When my fingers reached the edge of her panties I knew I would be expected to go further than I did last night, so I move to the center of her panties and felt her bulge. I wasn't sure what I should do, so I just rested my hand on her bulge, gently moving back and forth. The passion of her kisses increased, and with it, my boldness. I held her bulge through the panties and she nearly jumped.
"Just a moment," she said, and slipped her panties off, handing them to me. There was no mistaking her intentions now – I wasn't sure if I was really ready for this.
Clearly she was inviting me to go further, and it seemed the only right thing to do, so I reached under her skirt and took her into my hand, squeezing gently. I had never done anything like this before, but had plenty of experience handling myself, and this was similar – I just had never expected to do it for someone else!
Rachael moaned with pleasure and I knew she was getting aroused, and logically I knew I should find a way to pleasure her.
"Rachael dear," I said, "this is all so new to me – I'm not very sure of myself."
"I'm not sure of myself either, Marty," she said, "I don't have any specific expectations, so let's just enjoy our time together."
"If you feel you have taken the wrong path," she said, "I won't be offended if you back off."
"I don't plan to back off," I said, "but am not sure what next step I should take."
Rachael put her hand on my trouser leg and felt my erection. There was no denying that I was very aroused.
"Perhaps the next move is mine," Rachael said.
She knelt on the floor in front of me, and unzipped me, taking my cock out. Her pretty femme hands stroked me and I found myself lost in the moment. She bent over and took me into her mouth and I was at her mercy.
The feeling was wonderful, and the sight of this beautiful woman sucking me was incredible. Things were moving very fast and soon I came in her mouth. She just stayed there, holding me in her mouth while her pretty green eyes looked at me.
Suddenly a wave of shame came over me. It felt wonderful, but it seemed that I had crossed a forbidden line. Rachael had sucked me, but I was turning my best friend gay.
"I'm sorry I just lost control," I said, "I didn't mean it to be like that."
Rachael swallowed and smiled, saying, "but I meant it to be. – are you having regrets?"
"Only in what I might be doing to you." I said.
"Perhaps I was moving too fast," she said, "and you weren't ready for it."
"I'm going to go brush my teeth," she said, "I'll be right back."
What just happened was truly wonderful, but I didn't think I could every look at Ray the same way again. He was a cocksucker – or I suppose Rachael was – it was all pretty confusing. I wondered if Rachael would want me to return the favor – and doubted that I was ready for that.
Rachael returned and sat next to me, saying, "I'm glad you are still here – some men like to leave as soon as they cum."
"You must have a lot more experience than I have," I responded, "I had never been with a lady like you before."
"I'm not experienced at all," she said, "you are my first – I just read about other men online."
I kissed Rachael again – this time my tongue parted her lips and we enjoyed passionate kisses.
"Rachael dear," I said, "I would like this to go further, but I'm kind of scared about it."
"Too scared to spend the night?" she asked.
I just couldn't say no to such an offer, and quickly accepted. I said I would need to go back and get a change of clothes so I could go right to work from there tomorrow. I excused myself and drove back to my place.
As I drove I thought about what happened, and my response. I knew that I would have to pleasure Rachael, and wondered if a hand job would be acceptable to her. If she wanted me to suck her off I wasn't sure I could do it. In fact I wasn't completely comfortable with the idea of her sucking me off. It was wonderful – no doubt about it – but I wasn't sure how it would affect the complex emerging relationship.
I selected clothes for tomorrow and returned to Rachael's. She made a spot in her closet for me to hang my clothes. The closet was half male clothes (Ray's) and half Rachael's.
"I've been thinking about what just happened," Rachael said, "I want you to know that you don't have to return the favor – in fact I don't expect you to do anything."
"Well, I know that I can't arouse a lady and ignore her," I said, "I'm feeling unsure about my sexuality right now."
"I'm sorry if I have made you uneasy," she said, "I consider you a straight man, and don't expect you to act differently than that.
I breathed a sigh of relief and said, "but I still need to do something, and I'm not sure I'm ready for it."
"There is no rush," said Rachael, "a special man like you is worth waiting for."
–––––––––––––––––––– To be continued ...
Feel free to contact me with your comments or requests. –Bill (oral_guy_2000@yahoo.com)
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