Best Friend CD Part 6
Best Friend CD Part 6
by Bill Beaumonte (oral_guy_2000@yahoo.com)
This work of fiction contains explicit material intended for adults over 18. If you are under 18 or are offended by non-traditional sex, do not continue.
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Author’s note:
_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.
_
My Friday went well. It was a busy day but I had plenty of time to think about Rachel. I was able to look up several of the therapists on the internet and read about their practices. I made a couple phone calls and found that one nearby was taking new patients and made an appointment with Dr. Linsey Conrad. The therapist was a woman, which I thought might be better than a man. If she was a trans-woman herself that would be even better. No matter, I thought – at least we were on our way.
Rachel said she had to pack some clothes when she got home and would arrive about 7pm. That gave me time to stop at the grocery store and get dinner started. Rachel had made me a great meal the other night and I wanted to do something special for her. We both enjoyed a variety of ethnic dishes, so I decided to make some Lamb Ghallaba, a Lebanese stir fry that I thought she might not have had before.
I bought a bottle of late harvest Riesling, a slightly sweet white wine, which I thought would go with it. I put it in the fridge as soon as I got home for it to chill. I had time for a quick shower before I started dinner and made sure I shaved extra thoroughly – I didn't want to scratch any of her tender skin.
I reflected on some of what I had learned about transgender people and gender dysphoria. I was convinced that Rachel wasn't simply a guy in a dress – there was more to it than that. Rachel seemed really at home with the other trans-woman and she was willing to go to a therapist with me. I hoped that Dr. Conrad would help us sort out this confusing mess.
I'd been thinking a lot about it and decided that I was much too uptight about intimacy with Rachel. I decided that I wanted to kiss her intimately wherever it felt good to her. I decided that I really wanted to go down on her and was determined to do so – if I didn't lose my nerve. From the beginning I kept thinking that going down on her was giving a blowjob – something a straight guy wouldn't do! As I thought about how much I cared for Rachel, I realized that a man who cares about his lady would go down on her – no matter what she had between her legs!
Once I came to terms with that, I couldn't help but think about Rachel's lovely ass! I'd avoided it, even though it looked so luscious. As I thought about it, I found myself wondering about what it would be like to rim her. Rimming a woman was a long-time kinky desire, though I'd never done it. I don't know what attracted me to the idea – it seemed like such a dirty thing to do.
My desire to rim was one reason I stayed away from Rachel's ass. I couldn't help but thinking that if I rimmed her, I would have my tongue up a guy's ass – and that was much too queer for me.
After the support group meeting, I realized that I'd worked hard to convince Rachel she wasn't a pervert, yet I was afraid of the same thing. I knew in my heart that Rachel wasn't a perverted guy, but a woman – though a woman with a cock. As I had learned more about transgendered people I came to realize that Rachel was a woman, mostly because of what was between her ears, regardless of what was between her legs. I decided that I wouldn't cum until I pleasured her the way a man who cares about his lady should.
I knew that once I climaxed that I might feel differently, and just didn't want to risk letting her down. Tonight I was determined to do what I should have done all along, without any inhibitions.
I realized that I was spending too much time daydreaming about Rachel. I got dressed after my shower and hurried to the kitchen. There was a lot of chopping to do, and I got right to it. Soon I was cooking and figured out how I could get dinner to the point that I could start it simmering about the time Rachel arrives. That will allow me to focus on her while dinner finishes cooking.
Rachel was really important to me, and I realized that what I felt for her was love, and I was determined to do right for the woman I loved. I got the dinner simmering and did a little clean up. I uncorked the chilled wine to let it breathe and sat down for a breather.
Minutes later the doorbell rang – "no rest for the wicked" they say. I rushed to the door and opened it up. I just stood there and stared. Rachel was wearing a light blue frilly blouse, and a royal blue skirt. I couldn't take my eyes off her.
"Going to let me in?" she asked.
"Rachel, you're absolutely beautiful!" I said, stepping aside to admit her. She entered and set her luggage next to the door. I took her into my arms and kissed her. As we kissed, I slipped my hand down and fondled her lovely buns.
"That's a first for you," she said, "I thought perhaps you didn't like that."
"Darned right I do," I said, "I'm sorry I've been so timid about showing how I feel about you."
"Don't beat yourself up," she said, "You've just been politely reserved – a true gentleman. As your lady I'm giving you the green light to enjoy me as you wish."
I knew she would let me do what I wanted, so now I really had not excuse. Tonight was going to change everything for me. We continued kissing and I ran my fingers along her crack through her skirt – she moaned, and I knew I wanted her pretty ass.
My mind was racing, and I began to be afraid I'd mess up. She'd just given me permission to do what I wanted but would I have the nerve to follow through? Just then the kitchen timer sounded, signaling that dinner was ready to serve. We went to the kitchen and I dished up dinner and poured the wine.
The Ghallaba turned out well and Rachel said she loved it – she'd never had it before but hoped I'd make it again. We both liked cooking and looked forward to sharing the kitchen often.
After dinner Rachel insisted on helping me clean up, and I took every opportunity to steal a kiss. Rachel told me that by slowing us down I was just delaying desert.
"Oops, I didn't plan anything for desert," I confessed.
"No problem," Rachel replied, "I've got it covered, and it's a no-calorie desert!"
"I didn't see you bring any desert in," I said.
"Silly boy!" she replied, "I'm desert," with a sly smile.
"Then let's finish up here!" I said, and we finished cleaning up.
Rachel took me by the hand and led me to the living room and we sat on the couch. "Marty," she began, "I know you are struggling about being intimate with me. I love the way you kiss me, and I love going down on you. But beyond that I know things get difficult for you, and I don't want to pressure you."
"Rachel dear," I replied, "There is something I have been feeling really guilty about."
"I don't want you to feel guilty dear," she replied.
"I feel guilty about not taking good care of your needs," I said, "And I'm determined to remedy that."
"Marty, just being with you is enough for me," she assured me, "And just knowing how much you like to be with me is reward enough."
"Rachel dear," I said, "I think what I feel for you is love, and I need to take care of the lady I love – will you let me?"
"I'm not sure what you have in mind Marty," she said, "But I trust you completely, so do what you will."
I stood up and took Rachel by the hands and helped her to her feet. We embraced and kissed and once again fondled her soft buns. As we kissed I pressed ran my fingers up and down her crack through her clothes.
"That might be better under the clothing," she said.
"I agree," I replied, "And I feel very adventurous tonight."
Rachel smiled and said, "I hope your adventure includes me!"
I assured her that she was going to be central to my adventure and asked her to kneel on the couch, facing the back of the couch. She rested her elbows on the back as I knelt on the floor and lifted her skirt up, laying it on her back.
"I think I'm going to like this adventure," said Rachel.
I pulled her panties down to the bottom of her cheeks, and then kissed one cheek, then the other, and playfully licked her crack from the bottom to the top. Rachel moaned with pleasure and moved her knees further apart. I spread her cheeks, now for the first time gazing upon her tender rosebud. I was really aroused now as I drew closer to fulfilling a long-time fantasy. I must have jacked-off thinking about rimming a woman over a hundred times, and now I was about to do it – or was I?
I paused and stared at her. Without a doubt this was kinky stuff, but I wanted it. Still, could I really kiss her there? My arousal decided for me, and I drew closer. I licked her crack from below her rosebud, and then paused to kiss her there. Rachel moaned with pleasure and reached back to hold her cheeks apart, making it easier for me.
"Marty, that is so wonderful!" she said, and without further thought I plunged my tongue into her. To my relief she was wonderfully clean. All I could smell was the faint scent of soap and her perfume. I was really enjoying the way I was turning her on.
I continued for a few minutes and then found that my tongue was getting tired – I just wasn't accustomed to this, and wished my tongue was longer! I fully intended to get lots of practice, and hoped that soon I'd be able to do it much longer. I realized that Rachel was really turned on and knew I owed it to her to finish what I had started.
I pulled back and said, "That's all I can do for now, please stand up."
Rachel stood up and faced me. I put my hands under her skirt, reached the waist-band of her panties and pulled them down to her ankles. She stepped out of them and I tossed them onto the couch. Now I lifted the front of her skirt and began to kiss her soft legs, gradually moving up.
"Marty, you don't have to do this," Rachel cautioned me, but I knew I had to, and in my aroused state I really wanted to.
I brought my face to her crotch and felt her hard cock pressing against my face. I quickly opened my mouth and took her in. She was fully hard, but smaller than I was, making it easy for me to suck her. I didn't really know what to do, but just moved my tongue around, tracing the contours of her petite cock.
Rachel moaned and said, "You better stop before it's too late."
She was such a wonderful woman – so considerate – a guy would never have told me to stop. But I had no intention of stopping and continued. Rachel put her hands on my head and pressed me to her body, forcing herself into my mouth all the way. I was really beginning to like this and enjoyed the fact that she could easily fit all the way into my mouth.
I tasted her cum as she began to squirt. It was strong tasting, and I wasn't sure if I liked it, but it was Rachel's gift to me, and I wanted it. I'm not sure how long it took, but it was a blissful coupling – making me feel closer to Rachel than I ever had before.
"I'm so sorry Marty!" Rachel said in alarm as she pulled out, "I didn't mean to do that – I just couldn't help it. You can spit it out – please forgive me."
I swallowed and stood up. "There's no way I'm spitting out your gift to me," I said, "I should have taken care of you right from the start, and I promise to do my best from now on."
Rachel kissed me, forcing my lips apart and probing my mouth, as if to find anything not yet swallowed. That was one really passionate kiss, and Rachel was fondling me through my pants.
"I should return the favor," she said, but I stopped her.
"I don't want to cum now," I said, "I just want to enjoy being with you."
"A guy who says he doesn't want to cum would lie about other things as well," Rachel said, with a smile.
"Well, I kind of want to, as you can tell," I replied, "But I want to continue to enjoy what we just did."
"You're worried about the guilt feeling when you cum?" she asked.
I nodded, "I really wish it didn't happen – it really gets in the way."
"Marty, your feelings are part of who you are – I won't fault you for them," Rachel assured me, "We'll just have to work around them – the night is young, and we'll have more special time together."
"Rachel dear," I said, "I don't want to work around my feelings – I love you and I want to be able to pleasure you any time, without any hesitation – you deserve that."
Rachel smiled and told me we'd work on it.
We watched a movie together. I sat on the couch and she lay on the couch with her head on my lap. We gazed into each other's eyes for the longest time. It might not be polite to stare, but we seemed to be looking into each other's souls and I was completely lost in love.
"I love you Marty," she said after a time, "I did since our first date, but was afraid to say it – I didn't want to freak you out."
"It might have back then," I admitted, "But now it seems so right – when you love someone it changes everything."
After a while I reached down between her legs, touching her through the skirt. She hadn't put her panties back on, and I knew I was beginning to arouse her again. She pulled up her skirt, giving me direct access, and said, "You seem to like my clitty."
"Clitty?" I responded, "Yeah, I guess that's a better way to describe it."
"Well I'm pretty small down there," Rachel said, "And not really a man."
It seemed appropriate, and somehow thinking I was sucking a girl's clitty seemed right for me.
"I really like sucking you," I said, "And want to do a lot more of it."
"I'm glad you do like it," she said, "And perhaps you'll get over your guilt."
I continued to fondle her clitty and she invited me to suck her again, and I did so eagerly. Rachel sat up on the couch with her knees apart and I knelt on the floor between her legs. I took a moment to admire her erect clitty before taking her into my mouth. She ran her fingers through my hair as I sucked her. This was no blowjob – I was just going down on my lady and loving every moment of it! In a few minutes Rachel rewarded my efforts once again.
This time she couldn't pull out, so I stayed there until she drained completely. "Don't swallow yet," she said, "I want you to share it with me."
I pulled off her and brought my lips to hers. Our lips parted and her tongue darted into my mouth, taking some of her juice.
"That was amazing," she said, "But I think I'm done for the night."
We got ready for bed. When Rachel emerged from the bathroom she was carrying her wig, but wearing a colorful scarf on her head.
"I can't sleep in my wig – it would probably come off overnight anyway," she explained, "Is this okay?"
The scarf wasn't as nice as her hair, but it still made her look femme, and she seemed to feel better that way. I knew she didn't want me to think of her as Ray, and I was in complete agreement.
We got into bed and she lay close to me, resting her head on my shoulder. It felt so wonderful being close like that, and even more so when she firmly grasped my cock. It didn't take long before she had me hard.
"This will help you sleep," she said, sliding down and taking me into her mouth. I recalled rimming her and sucking her clitty, and soon I came. It felt better than any of the other times, and while my desire was fulfilled, the guilt feeling was much less.
It was still there, almost accusing me of being gay, but I just reaffirmed that I'd just pleasured my lady.
Rachel disengaged, and left to brush her teeth. Upon her return we cuddled and kissed before I drifted off to sleep.
To be continued . . .
Feel free to contact me with your comments or requests.
–Bill Beaumonte (oral_guy_2000@yahoo.com)