Best Friend CD Part 7    
          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.  




Please support this website by donating to Nifty.

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.

    In the morning I awoke, and Rachel was still asleep, and facing away from me. I slid over to her and snuggled close, spooning with her. My cock rubbed against her soft buns and I wondered how it would feel to be deep inside her. I remembered how much I enjoyed rimming her and thought about gently slipping into her rosebud. I sure didn't want to hurt her, so I'd need to go slow. I thought that a couple of lubed fingers might work well to open her up.

I had no idea how she would feel about it – most regular women wanted no part of anal, and maybe it would be taboo for Rachel as well – of course she did like rimming, so maybe there was a chance. I reached down and gently moved my hand along her cheeks, with one finger gliding along her crack. Judging how far down her rosebud would be, I slipped a finger between her cheeks and touched it.

Rachel startled me by saying, "It would work better with some lube."

I shouldn't have been surprised – why would she remain sleeping with me fingering her like that? I kissed her cheek and she rolled over and brought her lips to mine. It was a wonderful way to greet the day!

"You seem to be fascinated with my buns," she said.

"I really like to turn you on," I said, "You really liked it when I kissed you back there."

"You seemed to really warm up to it too," she replied.

"I sure did," I acknowledged, "But wonder what other ways I could please you there."

"Well, fingers are nice too," she said, "But what I really want is for you to take my virginity."

"I'd like that too," I said, "But I don't want to hurt you."

"Even a well-hung guy like you can do it without pain if you're gentle enough about it," she said, "It's something I've wanted, but never tried, so we'll learn together."

"Your virginity is a wonderful gift," I said, "I want you to be sure about this – you can only give it once."

"Maybe you have something there," Rachel said, "Maybe it is better given than taken."

"Sounds great," I said, "But I'm not sure exactly what you mean."

"Well, let's start with those special kisses you're so good at," she said.

With that Rachel rolled over, got up and swung her leg over me so she was kneeling over me with her gorgeous buns just inches from my face. As she brought herself down, she spread her cheeks, exposing her tender rosebud. "See anything you like?" she asked.

I put my hands on her hips and pulled her down to me, kissing her rosebud deeply. This was really a great way to start the day! Rachel moaned and that encouraged me more. Next, I felt her hand on my cock, expertly stroking me to attention. Then she did something that really felt incredible. I didn't know it at the time, but she lubed her hands and was stoking me wet – it felt amazing!

"I'm afraid if I keep this up, you'll cum too soon," she said. I was sure enjoying her rosebud, but never knew you could cum "too soon".

The Rachel pulled away, and I hated to see her rosebud leave me, but the she turned around and straddled me, lowering herself onto my slippery cock. It felt wonderful when my cock head was pressed to her rosebud. She just paused there for a moment and we gazed into each other's eyes.

Rachel began, "I give my virginity freely and without reservation to the man I love – the man I hope will be filling me regularly."

I watched the splendor of her lowering herself onto me, and feeling the wonder of her warm, wet inside. When I was in all the way she just sat there, enjoying the feeling.

Then she said, "Let's go for a ride," and lifted herself and then lowered, repeating a ride I'll never forget. I loved the view of Rachel bouncing up and down on me, but the feeling was even more amazing. I could only move a small amount but added to the thrusting as I could. I watched as Rachels clitty grew hard and bounced up and down in rhythm with her ride. I wanted to cum, but didn't want this to end – that must be what cumming too soon was about. I just wanted this ride to go on forever.

"See how you like my kegal's," she said.

Now she tightened up around me as she stroked, and timed the tightening with each stroke. I tried to hold back but this was just too much and I couldn't hold back my climax.

"I tried to last longer," I said, "But you were too much for me!"

"It felt wonderful for me as well," said Rachel, "I'm so glad you came – I wasn't sure if I could make you cum that way."

As I began to come down from my climax I looked at Rachel's hard clitty and knew I had work to do.

"Bring that clitty up here," I said.

"Are you sure you want to?" she said.

"Just get up here!" I repeated and she moved up and straddled my head, slipping her clitty into my mouth. I was still feeling a little reluctance – perhaps a little bit of remaining guilt, but I knew I had a duty to take care of Rachel, so I forced myself, and soon I found that I really liked the feeling of her in my mouth. She pressed her body to my nose, and her clitty still had room in my mouth. It just felt like her clitty belonged in my mouth and would for all time. As I sucked, my enthusiasm returned and the feeling of love I had for Rachel compelled me to do my very best. Soon she climaxed, giving me her juice, which I gratefully accepted.

"Waking up next to you is pretty special," she said.

"I'll say!" I agreed.

As Rachel got up, she glanced in the mirror and shreaked, "My hair!"

"It's over on the dresser, where you left it last night," I said.

"I should have had it on – I look terrible like this!" she said, beginning to cry.

"Rachel, I love YOU, not your hair!" I declared, "Of course your hair is really pretty, but YOU are the main attraction."

I got up and took her in my arms and kissed her, trying to assure her, with some success.

"We both should shower," she said, "But separately – I'm still not confident enough for you to see me as I am."

"That's okay for now," I said, "But we need to get you past those inhibitions. I need you to trust that I will love you however you are."

We kissed again and she excused herself, disappearing into the bathroom. While Rachel showered, I went to the kitchen and started some coffee, and looked around for something to make for breakfast. Should have thought about this earlier – I didn't have much for breakfast. I poured a coffee for each of us and took Rachel's to the bedroom. She was leaving the bathroom and had a towel around her head. She gratefully took the coffee and told me to hurry up and shower so we could have breakfast.

I had to shave first but didn't waste any time – eager to get back to Rachel. I showered and dried off, then got dressed. I went to the kitchen to find Rachel wearing a very shear robe under which I could clearly see her bra and thong panties. She had such beautiful cheeks!

"Why don't we skip breakfast and go right to desert?" I asked.

"You horny guy!" she said, "But you need to keep up your strength so you can do all those amazing things for me!"

I settled for a little smooching, and saw that Rachel had prepared Eggs Benedict in the short time I showered – a pretty impressive accomplishment – I couldn't help but think that she'd make a wonderful wife!

I refreshed our coffee and poured us both some orange juice as Rachel dished up the eggs. We enjoyed a first-rate breakfast thanks to Rachel's kitchen skills. As we ate, Rachel said, "Your post-climax guilt seems to be better now."

"Well, it started out as guilt, but got weaker, and now is simply reduced desire," I replied, "My arousal was over, but not my love for you."

"So, it was love, and not desire that was behind your oral attentions?" Rachel asked.

"Love was certainly the driving force, but even without arousal I've come to enjoy kissing your sensitive places," I explained.

Rachel leaned over and kissed me on the cheek, adding, "I know what you mean – I don't need to be turned on to enjoy pleasuring you. For me it's a thrill just to drive you wild!"

We cleaned up the kitchen after breakfast Rachel insisted on changing her clothes before we went out. We were just going out to a shopping mall. While that seemed kind of routine for me, it was a big deal for Rachel. She had been dressing for much of her life, but nearly always in private. I was helping her with a long-standing dream to be out in public as a woman. She was afraid to try it on her own, but I convinced her that she would be completely safe with me.

Rachel put on a pink dress that looked stunning. She put slipped on some pink heels and modeled the outfit for me. Watching her walk, with her hips rocking back and forth made me long to kiss her buns, but she told me I'd have to wait, but that I'd get all I wanted later.

We got into my car and Rachel turned to me and said, "Please don't leave me alone – I'm excited but kind of scared too."

"I won't let anything bad happen," I assured her, "I'll be with you the whole time."

She squeezed my hand and we set out. When we arrived, I parked and instructed Rachel, "Now just stay there and wait for me to get the door."

Rachel smiled and waited patiently as I got out and opened her door, offering my hand, which she took. "Such a gentleman!" she said.

"And you are my lady," I replied, "And I expect you to act accordingly – I open the doors, and you wait for me to do so – got it?"

"Yes sir!" she said, smiling broadly.

  To be continued . . .

Feel free to contact me with your comments or requests.
    –Bill Beaumonte (oral_guy_2000@yahoo.com)