Diamond's Best Girlfriend

Diamond and I were talking not long ago, and she told me that while we were on the line her girlfriend texted and cancelled out on a big girls day they had planned for the upcoming weekend. They had made plans to go shopping, visit their favorite spa for manicures and pedicures, eat out somewhere, and have what I would describe as a "girl's fun day" together. Diamond had been really looking forward to it. Now it had fallen apart. I told her that I have always had a "girls day fantasy" of my own, the fantasy is to spend a day with a close woman friend, and essentially be her girlfriend for a lovely day, just like the one Diamond said had fallen apart on her.

Here's a tip, something I only learned recently: if you're a submissive and you're friends with or you are a sub to a Domme, don't mention anything in the same area code as having desire for, or even curiosity about feminization to her. Well, not unless you want to do it. Because she is going to run with it. Diamond is no different.

Not long after that conversation, Diamond and I were talking on the phone again, and she asked when in the not too distant future I thought I could fly up and see her again for a few days. I asked her if she had some kind of a D/s scene in mind for us, and asked her to tell me what I needed to do to get ready. "This is just a visit," she said, "just a visit between two really good friends" Diamond and I had become really good friends. I love talking to her and I really love her company when I can be with her, so I rearranged my calendar, set up the flights, and rented a room. I gave her all the details and arranged for her to have access to the hotel room before my arrival. To say I was excited about seeing her is an understatement.


I arrived at our hotel from the airport late on a Tuesday afternoon and took a cab to the hotel. I found Diamond already there waiting up in the room. She was beautiful as ever with her caramel colored skin, piercing hypnotic brown eyes, full kissable lips, and her hair tied back showing a sexy neck. Her short, sweet, sexy figure is a perfect compliment to her gorgeous face. And don't let me leave out her prominent, kissable, lovely booty, a booty I can look at all day long and never get tired of looking t it, not even for a second. Her pretty feet were shown off, too, in a pair of open, strappy sandals. Diamond is the whole package: yes, all of it and then some.


"I've planned a little surprise for you, if you've got an open mind." She turned and pointed toward the bed. There on the bed were what appeared to be three, four, maybe five pairs of very feminine looking pink panties. "Pink means girls day! Tomorrow's going to be your lucky day! You are going to have so much fun. And I am going to have so much fun with my new girlfriend." She told me that she wanted to make my girls day fantasy a reality, but only if I agreed to go along with anything and everything she wanted to do and if I promised that I would do everything she asked me to do.

Of course, I agreed right away. This girls day thing had been a fantasy of mine for so long, but I don't think I know anyone else who I trust enough and care for enough to do it with other than Diamond. I was already over the top with fondness and affection for her, to have her make this happen for me had me totally over the moon. I have to admit, because I know Diamond pretty well, and considering I had promised to do anything and everything she wanted me to do, I was also a bit apprehensive. Diamond was not going to be one to go halfway with this, not a chance.


She ordered us room service: simple chicken tenders and fries, two pitchers of peach mango daiquiris, and a tray of cookies and sweets for later on.
 While we waited for dinner, she told me I had a lot to do, so I better get busy. She told me to run the bath, we had a lot of shaving to do before tomorrow.

"Define 'a lot of shaving', Diamond."

"Everything below your ears, gone: back, chest, hands, arms, legs, feet, butt, and your pretty little cock, too," she said. "And I'll help you with all those 'hard to reach' areas. We need you to be all smooth and pretty."

I ran the bath using the "Premium Beauty Lilac Blossom Bubble Bath" product she had prominently positioned there to bubble the water. There was a pink can of shaving cream laid out along with an opened two-pack of women's razors and a pair of scissors. There was also a very familiar looking blue pill, a small glass of water, and a note that said, "Take this pill first." Diamond had thought of everything and Diamond had come prepared.


I took my pill while the tub was filling and started to get undressed.

"Call me when you're undressed," she called out.

When I was undressed I called her and she came in and whisked away my clothes, "You won't be needing these tonight." I shyly covered myself. "You don't need to be shy. I've seen you naked before, and I'm here, aren't I?" I let my hands relax to my sides and my three quarters erection waved at her. "I knew this would make you happy," she smiled. She was wearing a cute black robe, made of lace with a pretty silky ribbon around her waist holding it together. "Call me when you need help with any hard to reach places," and she was gone.


I got in the tub and sunk down into the sudsy, fragrant water. After I acclimated myself to the warm bath, I meticulously shaved my feet, and legs, which was fairly easy. Then I shaved each arm, even the little hairs on my fingers and the back of my hands. I was going along with everything she's asked, and I was doing my best to fully enjoy the reality of my fantasy come to life.

I heard a knock at the door. Room service was here. A minute or two later, Diamond came in drinking her daiquiri and handed one to me, too.

"A toast! To the best girls weekend two girlfriends have ever had... my Mattie girl." We took a little drink and I got back to work.

"I've never shaved my underarms before, Diamond."

"It's easy, Mattie girl. Let me help you. First, let's cut as much of the long hairs under there with the scissors. The rest will shave off really easy."

I raised up my arm and she trimmed me with the scissors. She's not a hairdresser, but she was pretty efficient with the scissors, and the rest shaved off quite easily with the shaving cream and razor.

"Stand up, lemme get your back." She giggled when I stood up. "What a cute little butt, makes me just want to smack it!" Whack! She did, too. One big smack with bath bubbles flying everywhere.

She proceeded to shave my back and had me open my cheeks and shaved my butt, too. All of it. The back of me was hairless from the neck down. I should mention that her shaving my butt like that sent shock waves through me, and with the added energy the blue pill sent that way, my cock was fully erect. A modest 5-1/2", 6" if I'm being generous to myself, was standing proud and happy to see her.

"Turn around and clasp your hands behind your back. Keep them that way till I tell you that you can let go." I clasped them by the small of my back like a military guy does standing at 'parade rest'. She smeared my entire chest with the shaving cream and started a slow and careful process of shaving it, seemingly ignoring Mattie girl's boner being so uplifted and happy to see her. When my chest was smooth, with just shaving cream remnants on it, she stroked my pecs and lats, and up around my neck. Without warning she put her arms around my neck and kissed me with the kind of kiss people hope for in a lifetime. Her soft lips felt like pillows on mine. She took my head and neck firmly in both hands and kissed me again, this time exploring my mouth with her tongue, and me likewise to hers.

Her left hand let go and dropped, but her lips and right hand stayed where they were. I felt her take my cock in her now free hand. "You are going to have sooooooo much fun Mattie girl. Sooooo much fun. And so am I! Now, let's get my new girlfriend here shaved."

Between the scissors, the shaving cream, and the razor, she handled my cock like it was her own, pushing it this way to shave over here, that way to shave over there. She pushed it down to shave all around my pubic bone and pushed upward as she carefully tended to my nut sack. I was as hard as I can ever remember. The whole thing was sexual, intimate, and had me hot and horny as can be, I was completely blown away by how she shaved and touched me. It was heavenly. And then all at once, after what must have been an hour total in the bath, it was done. I was as smooth from the neck down as I ever was. My cock was hard as a rock, too. She threw me a towel, and I toweled off. Your clothes are on the bed. There on the bed were a pair of pink lace panties and a pink robe that matched her black robe and black lace panties perfectly. She also had matching pink fluffy slippers for each of us. In our robes and panties we drank daiquiris and ate our dinners. It was really nice, and it felt wonderfully intimate. I was already mad about this woman, but every new experience with her seems somehow better or more meaningful than the last.

After dinner I put the tray outside, Diamond giggling at me because I was being super careful in case anyone saw me. When I came back inside she said she had a special surprise for me.

"A surprise? What, this whole thing is a surprise!"

"Well, this is something special, something I want you to have to remember this forever. Do you know how Diamonds are a girl's best friend"

"Sure, everyone knows that line."

Handing me a box she said, "Diamonds are a girl's best friend, but you are Diamond's best girlfriend."

I opened the box and in it was an ankle bracelet inscribed with the words: "Diamond's best girlfriend."

"It's beautiful, Diamond. You really didn't have to." She took the bracelet from me, and bent down, opening the clasp. 


Putting it onto my ankle and clasping it, she said, "Here's what I want you to understand, Mattie girl. When you are wearing this, it is to remind you that you promised to do everything and anything that I asked you to this weekend. And for the duration of the weekend, while you are wearing it, I expect you to do exactly that. Understood?"

"Sure Diamond. I'll do everything and anything you ask as long as I'm wearing this ankle bracelet."


We snuggled on the couch and watched some Netflix and drank and laughed. We had some cookies and just had the nicest of evenings. Once in a while, for a minute or two, I'd forget what I was wearing. But feeling the robe and panties on my never before smooth body kept reminding me: lace panties and a lace robe.

Right as our movie was ending, she took my hand and slipped it into her panties. I knew what to do and slid it down to her smooth, pussy. I played with it, taking her outer lips between my fingers, massaging her fleshy mound and making sure to move her inner lips back and forth underneath that flesh, left right, left, right, left, right, left. We were kissing and snuggling and I massaged the flesh on her pubic bone, her outer, and her inner lips with full intent of nothing but bringing her pleasure. As my hand worked her sex to a wet and then wetter frenzy, she let me know what she wanted.

"Eat my pussy, girlfriend. Make me cum, Mattie girl."

I knelt in front of the couch before her and she slipped the black lace panties off and tossed them aside. Her legs were parted and she welcomed my face and mouth between them. Her smooth shaven pussy is a sight to see for a pussy worshiper like me. Her smooth outer lips surround inner lips that flare ever so slightly like petals on a just opening flower. The lips are pinkish brown, with brighter pink at the bottom and around her hooded clit.


She wasted no time taking my head in her hands and guiding my mouth directly to her wet lips and stiff little clitoris. "Lick me and make me cum."

I licked her lips up and down. She smelled so much a wet, sweet pussy that I wanted to taste, smell, and feel her with my lips and tongue forever, but she was ready for more focused efforts right then. Unhurried but deliberate, I was in heaven and doing my best to take her there, too.


"Lick my pussy Suck my clit. Suck my lips. Lick my clit."

I did as I was told, enjoying the heaven that lies between her legs. Heaven, that's where I was. I was in heaven. Licking and sucking. I kept looking into her eyes, and she looked into mine when hers weren't closed. Flicking and licking. Flicking and licking, licking and sucking. I felt her grip on my head tighten and she pulled me so that may face was just full of nothing but her smooth, very wet, perfect pussy. Her hips were in a grind. She was climbing the mountain and she was using my head, face, lips, and tongue for traction. And then, it was upon her. Her eyes shut tight, moaning and crying out, her head thrashing back and forth.


"Don't stop, don't stop. I'm going to... I'm going to... I'm cumming..."

It must have been a good one. She was flowing, so wet, so much all over me. I was a pussy soaked mess. I was a happy, pussy soaked mess.

"Oh, my god that was so strong. So good. So nice."

I leaned back to smile at her. She smiled back at me.

With a sly smile, she asked a question she already knew the answer to. "Are you still wearing your ankle bracelet?"

"Of course I am."

"I know you are. You know what I want?"

"What do you want, Diamond?"

"I want to watch you jerk off in your panties, that's what I want."

"Right now?"

"Yeah, right now, standing right here, in front of me looking at me while you do it. Take them off and wrap them around your cock and make yourself feel good. Make yourself cum. Don't stop looking at me, into my eyes till you're done."

I took the panties off my aching, drooling cock and wrapped them around it, took myself and the panties in my right hand, and started to stroke. And stroke I did. The panties felt a little different on my smooth cock. But they were as soft as I was smooth and once I found how tight to hold, the stroking felt really good,

"Does that feel good, Mattie girl? Tell me how good you feel."

"Oh, Diamond. It feels sooo sooo good. Sooo goood."

I was getting closer and stroking faster.

"Look in my eyes and cum. Cum for me Mattie, Cum!"

Oh my god I am cumming!"


And I came and came. It felt so good. Spasm after spasm. Every drop straight into the panties. I just came and came and came. It was amazing.

Afterward, we threw our sex-wet clothes on the bathroom floor and took a nice shower together in the oversized shower. We shared a romantic kiss.

I said, "I can't wait for tomorrow."

"Neither can I. I can't wait."


She give me one last gift that night for sleeping, too. For sleep she had bought us matching panties and matching customized oversized t-shirts to sleep in that say: "So excited for Mattie's first girls day" on them. She turned my pair around and I saw that my panties had an iron-on across the butt that said, "My 1st Girls Day!". Hers simply said, "Diamond".


We put our new pjs on, climbed into bed, snuggled and kissed goodnight, and I was asleep in no time.


We woke up fairly early Wednesday.

"Good morning, Diamond."

"Good morning, Mattie girl!"

"I had so much fun last night being your girlfriend. I'm really excited for today, too."

"Me too. You were soooo cute last night. Adorable! And you're still sooo cute in your pink t-shirt and panties." She was beaming. It was obvious that she was having a great time giving me my girls day fantasy.


I blushed. This was all new territory for me.

We both got up and took turns with the bathroom. She went first and I went second. When I came out she was laying on the bed on her stomach wiggling her beautiful, juicy looking booty. She still had on the oversized t-shirt, but the panties were gone.


"Come here and rub my booty, Mattie. I know you want to rub my booty."

I came over, climbed onto the bed in a good position to rub that magnificent butt. And that's what I did. I alternated between gently skimming the surface of her bottom, to rubbing with a little more pressure, and then at times using two hands I kneaded her bottom, making each cheek slide along the other along the butt crack border that separates them. It was wonderful. It felt intimate and sexy and sensuous and special, all at once. After four or five minutes of my focused attention, she started to squirm.

"Kiss my booty good morning, Mattie. Kiss my booty to wake her up."

I leaned over and kissed her bottom. I kissed it here, over there, up, down, left and right. I spattered kisses everywhere. I kissed up on the small of her back, and down to the bottom of her behind where the butt meets the rear upper thigh. I was generous with my kisses, some soft like butterflies landing, some more sensuous and erotic, and some with little nibbles. I could eat her bottom every day and never tire of it. She started to squirm, and all at once, drew her right knee and then the left up under her. She was buns up, face down on the pillow. What a sight!

"Kiss it. Kiss the whole booty," she wiggled her hips and bottom seductively, sexually.

I moved behind her and positioned myself. I could see her pretty, clean shaven, brownish pink pussy was already glistening with wetness, and her little brown rosebud butthole was clenching and un-clenching in anticipation.


"Kiss it. Kiss my booty, Mattie!" And I did. I dove in and put my lips right on her little rosebud, then after lingering a second, exhaling my warm breath on it so she could feel the closeness of my nose and mouth to her sensitive behind. I could see that she had her hand playing with her pussy.

I was slow and methodical. I wet my lips and kissed all around her puckered hole. I traced the tip of my tongue across it, first from bottom to top, then top to bottom, switch to and from a similar left to right, right to left pattern. I was unhurried, lingering, sensual, and deliberate. She was squirming dramatically. I glanced down and I could see that she was fingering her pussy, her index and ring finger on each side, and her middle finger was disappeared into her perfect, beautiful little hole. I took the hint and penetrated her ass with my tongue.

"Tongue fuck my ass, Mattie. Tongue fuck me now!" I started an in and out rhythm, tongue fucking her bottom while she fingered her pussy. There was no rush, no urgency. It was amazing. When my tongue was inside her, I started a tiny 360º rotational movement with my head so that my tongues was applying pressure in an around and around motion. I hear her breathing start to get more and more excited, and her moans were increasing in intensity.

"Mattie, Mattie, Mattie! It feels soooooo good!" I just kept in with alternating in and out and round and round and she kept fingering herself, applying pressure to her clit and penetrating her vagina. It was amazing. And then the dam broke.

"Ungh... I... am... cumming..." Her hips were bucking so hard it was hard for me to stay on her butt. "Ah ah ah ah... feels soooooo goood!" She came down rather slowly, and then in a few minutes, it was over.


Still energized by the lingering erection medicine, and fully aroused by the highly erotic and intimate activities of the last twenty or thirty minutes, I was fully erect in my pink panties.

Pointing at it, Diamond said, "That'll have to wait, we've got the get busy. We have a busy day ahead."


After our showers I shaved my face again, and applied moisturizer to my smooth skin. Being completely shaved was still quite a novelty. Just rubbing the cream in seemed erotic and sensual.


When I came out of the bathroom, Diamond had yet another surprise for me. She handed me a small, silver butt plug with a pink heart in a crystal type pattern on the base, some lube, and a pair of pink boyshorts panties made of a stretchable lace material.