Best Friend CD (part 4)
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.
––––––––––––––––––––
Rachael led me into the bedroom and told me I could use the bathroom first to get ready for bed. I brushed my teeth and put on a clean pair of shorts. I didn't wear anything else to bed, so I was ready to go. I was a little nervous because going to bed with a girl usually meant sex, and as much as I found Rachael attractive, her boy-parts made me a little shy about it – hell, it made me a LOT shy about it!
I got into bed and waited for Rachael. When she emerged from the bathroom she was wearing a red robe over a pretty red nightie. She had no bra on underneath but was wearing black panties. She removed the robe and climbed into bed, turning off the light. "I'm keeping the panties on," she said, "unless you want to take them off me." I wished I had the courage to pull the off and pleasure her.
She lay next to me and we kissed. I put my hand to her chest and felt small, but definitely feminine breasts. "Very nice breasts, Rachael," I said, "I wasn't expecting this."
"I've been taking a low dose of female hormones for several years," she responded, "they have developed slowly, but make me feel better about myself."
"Rachael dear," I said, "I'm confused about who you really are – you look and act really femme. I didn't realize a cross-dresser would be so womanly."
Rachael put her head on my shoulder and snuggled close. "When I am Rachael I really feel like a woman – and it seems like who I really am. When I am Ray it sometimes feel like I am in disguise – not the real me."
"I really liked it when you went down on me," I said, "but felt kind of strange about it afterwards."
"You mean because your best friend just gave you a blowjob?" she asked.
"Since you put it that way," I replied, "yes, and I don't want to be the cause of my best friend becoming gay."
"It was the first time I ever did that," confessed Rachael, "in fact it was the first time I have ever been with a man. It was a little confusing for me as well. I wanted to please you, and felt like I was a woman when I sucked you."
"That never occurred to me," I said, "Could you do things as a woman that you would never do as a man?"
"Yes," said Rachael, "at least I think so – this is all so new to me too."
"So you think Ray would not like me to ask him for a blowjob?" I asked.
"I think if you are nice to Rachael you will get more," she said, "but not from Ray!"
"Rachael, I really like being with you, and you really turn me on," I said, "but I'm not sure about having intimacy with you."
"Not sure you want to?" she asked.
"Part of me wants to – a lot!" I said, "but part of me just can't do it."
"Well," replied Rachael, "I'm not expecting you to do anything to or for me, but I'll take care of your needs."
"That just isn't right," I insisted, "a man should take care of his lady and part of me really wants to, but I'm straight."
"I'm sorry I got you into this," she said, "I'm some kind of sick pervert and I've drawn you into this now. I never wanted to hurt my very best friend."
"There is no harm done," I said, kissing her, "I don't understand this, but somehow we need to figure this out. This isn't normal, but I really like you, and we need to sort this out."
I took her in my arms and suggested that we sleep on it and deal with it in the morning.
We drifted off to sleep spooning – she felt so nice, close to me like that.
The next morning was Saturday and as I awoke I could feel Rachael's hand around my cock. I turned to her and kissed her as she stoked me.
In the morning light I could plainly see her small but beautiful breasts. I pulled her to me and sucked one nipple, and then the other. She sighed with pleasure as I did, and I found myself wanting to pleasure her, but holding back.
I reached into her panties and took her into my hand. As soon as I did her kissing became very passionate. I loved the effect I was having on her, but felt very uneasy about what I was doing. Our tongues danced together as we kissed, and I felt her harden in my hand.
Finishing our kiss, I looked her in the eyes and said, "I don't think I can do much more for you than this."
"I'm not expecting you to," she said, "do what you think is right."
"That's the problem," I said, "What I think is right is to fully pleasure you, but I just can't. In fact I just can't reconcile my feeling for you with being straight."
"Marty dear," she said, "I don't want to threaten yours straightness, but it seems that I am."
Rachael rolled away and sobbed uncontrollably. "Rachael," I said, "I'm so sorry dear."
"It's me, not you," she said. She got up and dried her eyes, and said, "would you get dressed and wait for me in the living room, please?"
"Sure dear," I said, kissing her. I got dressed and left the bedroom, closing the door.
This sure was a confusing mess for me. I found Rachael really hot, and almost felt I would turn gay for her if I had to, and I really wanted to be with her – but I was straight and didn't really want to be gay!
The door opened and Ray stepped out, saying, "Marty, we really need to talk."
"I guess so," I said.
We went to the kitchen and prepared breakfast together, each keeping a comfortable distance. I hoped that I was not witnessing the end of a wonderful friendship.
Ray began, "I've been secretly cross-dressing for most of my life, but it's been a secret, and never intended to draw you into it."
"I suppose things were fairly simple until I got involved," I said.
"Yes, but you made me feel more womanly than I had ever felt before!" Ray said.
"Is it really true what you said about feeling that Rachael was the REAL YOU?" I asked.
"Yes," Ray admitted, "but I don't really understand it – it's like I was a woman born into a man's body, and only feel completely real when I'm a woman."
"I've heard of something like that before, and about how some men become women – more than just cross-dressing," I said, "can I use your computer?"
"Sure," said Ray, and turned it on and logged in for me.
I pulled up Google and typed some search terms. At first I got some porn sites, but not what I was looking for. Finally I found what I was looking for.
"Yes, here is it – now I remember – it's called gender dysphoria – where you don't like the your birth gender. Look Ray, there is an online test – try answering these questions.
Ray took the keyboard and answered about a dozen questions. The response indicated that was likely to be gender dysphoric, but it should be confirmed by a counselor.
"Just what I need!" said Ray, "a fucking shrink! I don't need someone to tell me I'm not normal – you and I both know I'm not!"
"Wait," I said, "let me search some more." I continued and found a search for transgender support groups. Searching their listings I found one met in a city about 70 miles from us. I wrote down the phone number.
"What are you going to do?" Ray asked.
"I'm going to call and see what I can find out," I said, "if there are people who understand this sort of thing, that might help sort this out."
"Wait a minute!" said Ray, "This has been my secret for most of my life. I just recently let you in on it, but I"m not ready to open up to a bunch of strangers."
"Ray, they might be able to help," I said, "and because they are strangers, far from her, there is no risk of your secret getting out around here.
Ray responded, "Okay, check it out, but don't do anything yet." I agreed.
I went home, hoping that Ray and I were ok. At home I called the number for the transgender support group and explained that a good friend of mine may be gender dysphoric and I was hoping to connect with some people who could help.
I suppose a lot of people called the number pretending it was for "a friend" when it was really for them. They asked me how long I had felt that way and I had to reaffirm that it wasn't me, but it was my friend. They told me that the met monthly on the second Thursday, and gave me the address. They said that "my friend" was welcomed to come dressed as a woman and that her boyfriend was welcomed as well.
That sure was a strange conversation. I called Ray and told him, but he was still very reluctant. I asked him to think about it and that I would go with Rachael. He said he would think about it, but Rachael probably wouldn't be around much for awhile.
The meeting wasn't for a few weeks, so I thought I'd have time to convince him.
Over the next few days I only saw Ray a few times, and he seemed a little distant – perhaps he felt ashamed.
On Friday night I called him and said I wanted to stop by to visit and would bring some beer. He seemed reluctant, but agreed.
We talked about guy stuff most of the time, as if nothing unusual had ever happened. After a few beers I found the courage to finally say what was on my mind.
"Ray, I want to take Rachael to the support group meeting next Thursday," I said, "do you think you could convince her to go with me?"
"I'm not sure about that," he said.
"PLease Ray," I said, "I feel really strongly about this."
"Can you give me about half an hour and I'll see?" he replied, "have another beer while you wait."
I was feeling pretty mellow by now, and was relieved that he wasn't angry with me. I watched TV while I waited, an then heard a girl's voice calling to me, and looked up to see Rachael!
She was really wonderful to see, and I went right to her and kissed her.
"I'll go with you next Thursday," Rachael said, "but I'm kind of scared about it."
"Nothing bad will happen," I promised, hoping I knew what I was doing.
"You must really like me," she said.
"I do," I said, "and Ray."
After a few more kisses I excused myself and went home.
–––––––––––––––––––– To be continued ...
Feel free to contact me with your comments or requests. –Bill (oral_guy_2000@yahoo.com)
Please support this website by donating to nifty.org