Diamond's Best Girlfriend

"I've never used a plug before."


"It's just a small one, it'll be nice for you to feel it inside you all day. Put it in and then put the panties on. I want to watch," a sly smile on her face.

I smeared a bit of lube onto the plug, squatted just a bit, and pushed it against my tight butt. It slipped in easily. I put the panties on. We dressed, me in my boy clothes over the pink lace panties: blue jeans, a white t-shirt, my favorite pair of Pierre Cardin loafers, and a "Diamond's best girlfriend" ankle bracelet that signified my promise to go along with whatever it was that Diamond wanted to do today. Diamond was dressed similarly, her butt looking epic in her jeans and in a white t-shirt. She had a pair of strappy heels on that showed off her pretty feet. I was quite aware of the plug in my bottom as I finished getting ready to go. It was almost 11:00 a.m. as we headed out the door.


We caught a cab and made our first stop a pancake place, Diamond's favorite. She opted for lunch, chicken fajitas and a Pepsi Light. I had pancakes, sausage links and coffee. I squirmed just a bit as we ate. I'd never worn a plug before and I was keenly aware of its presence in me.

Our next stop was to a nail salon. Diamond had arranged for us to get his and hers pedicures and manicures. Well, they were more like 'hers and hers'. I was more than just a little embarrassed when she picked out a cute pink color and then announced to the girl at the counter, "For him."

I sat and had my fingernails done right next to where Diamond got hers done. My nails are short, Diamond keeps hers very long. Diamond had so much fun talking to the nail girls about how cute I was going to look and how "pink is his color'"and on and on and on. And although I blushed again and again, I admit, I was having fun, too. Diamond gave her phone to the receptionist and had her take pictures of us getting our nails done together.


I'd almost forgotten my ankle bracelet. I remembered it immediately as the girl began to roll up my jeans leg for the pedicure. "Nothing I can do about it now," I thought. She looked up at me with a sweet smile when she saw it, and even turned it around my ankle to read the inscription. "Diamond's best girlfriend".

I pointed. "Diamond."

"Ooooh. Very sweet," she said.

The pedicures were otherwise uneventful, except it was going to be at least a half hour until the pink polish on my toenails dried enough for me to put my shoes back on. Diamond took some more pictures, this time of the girl painting my toenails. And I might mention that sitting in the pedicure chair I was keenly aware of the plug in my ass.


"Oh, Mattie, you look soooooo cute!" She was having a great time, an absolute ball.

We left the salon and headed to the mall, which was just a block or so away. First stop was Macy's for panty and lingerie shopping.

"Show me which panties you like best, Mattie girl!" She was giggling and bubbling over with fun.

Again and again I picked out the girliest, flowered, ribbons, bows, satin, lace, frilly, panties in pink and lavender, pastels, and prints. There were briefs, bikinis, thongs, boyshorts: something in every style. Diamond took delight in holding them up against my jeans and imaging out loud, a bit louder than discrete, how they'd look on me, or asking the sales woman if she thought they had them in both our sizes so we could match. We shopped the entire panty section, and even looked at nighties and nightgowns. By the time we hit the checkout counter, we had at least nine or ten matching pairs, one each in both our sizes, "so we can match" is how Diamond explained it to the cashier. I set a new personal record for embarrassed blushing in Macy's, all thanks to Diamond going out of her way to tease me good naturedly. I was having more fun than I was embarrassed, though.


The mani, pedi, and shopping at Macy's had taken awhile. We needed a snack and stopped at Ann's pretzels. Diamond loves Ann's Pretzels. She had a sweet pretzel and a Pepsi Light. I had the traditional salted kind. It was good to rest and regroup for a few minutes after such a busy day already, and still more fun to be had.

Next stop was Victoria's Secret. We shopped the same way we did at Macy's, discussing my likes and dislikes about all the different panty styles and colors. And of course, there was more of Diamond sizing things up against my jeans. She found us some nighties in the back, and said we needed to try them on. We walked over to the fitting rooms and she showed the girl that "we" had to try on our new nightgowns. First up was a babydoll in a very sheer purple color, that had soft faux fur all around the bottom and matching bikini panties. When we were both dressed in them, Diamond got out her phone and took a whole bunch of selfies.

She stroked me through the panties, and in no time flat my smoothness had turned to hardness. Peeling down the waistband just enough, my erection sprung free and jutted straight out, the panties containing my balls, the shaft and head out and about above.

"Oh, that is soooo cute. Your dick looks so cute sticking out of those panties. I could just look at it all day!" Click. Another picture. I have to say, I was having so much fun. By the time we checked out at the cashier, we had another seven or eight matching pair each in our respective sizes, a couple of new nightgowns, and matching pink, fluffy slippers. The slippers are adorable.


We stopped in one of Diamond's favorite stores for shopping with the girls, Forever 21. She said, "Let's play a little game. You pick out something for me to wear, and I'll pick out something I think you'll look cute in, and we'll model them for each other back at the room tonight!"

"Okay. What size should I get for you?"

"Usually I'm a small. We can use the fitting rooms again if you want."

"Well, let's just see how we do, you can return them and get a credit of they don't fit."

So, shopping we went. I looked at some blouses and some dresses, but none of them was something I was really hoping to see Diamond in tonight. Then I spotted a cute satin bodysuit with lace trim. It was somewhere between pink and purple, and I knew from the mannequin that Diamond's butt would look fantastic in it. I grabbed it in a small and went to the check out, then stepped into the mall and sat on a bench while she finished. Diamond came out a few minutes later. Diamond isn't one to wait for a surprise, and asked right away, "Show me what you got me?" Her beautiful brown eyes all puppy-dog cute, I couldn't say no.

"Well, if I show you mine, you have to show me yours, deal?"

"Deal."

We traded packages. She had picked out a tie-dyed sports bra and matching leggings, about the same length as Capri pants would be, of course in a pink tie-dyed pattern. It was very cute, and being a stretch fabric, I was sure it would fit. When we left Forever 21 we were pretty much loaded down with bags from all our shopping.

But Diamond still had one more stop in mind. We hailed a cab and got in. Diamond directed our taxi to a sex toy shop she had found that was on the way back to our hotel.

"We need to find some toys to play with at the hotel tonight. This will be soooo much fun! I love these kind of stores!" I looked around and was a bit overwhelmed at the array of all manner and sort of adult toys displayed on the wall.

"Mattie, go ask the man at the counter where the strap-on dildos and harnesses are." I looked at her sheepishly, and she tilted her head a little sideways and gave me 'a look' and said, "You promised."

I walked rather sheepishly over to the guy behind the counter and asked him where the strap-ons are located. He smirked and pointed to the section of the wall where they were on display. I got Diamond and we went to shop for a strap-on. I'd have grabbed one and got the hell out of there, but Diamond was shopping like she was looking at a new car or something. She was reading labels, comparing dildos, and looking at them with a very discerning and practiced eye. She handed me one with a 7-inch dildo in it. "Go ask him if he thinks this is a good size for a beginner."

Beet red, I took it back to the counter and asked the guy, "Do you think this is a good size for a uh, a uh, a beginner?"

"It's a great size for a beginner. Your ass will never be the same. You're going to love it. You might even like to go to an 8-inch. It's more filling." I decided that the 7-inch was plenty.

By the time I got back to where Diamond was, she had a fancy looking, vibrating realistic penis dildo, also about 7 inches and handed it to me to hold with the strap on. She led me to a display of butt plugs. She picked up a 3 pack with a small, about the same size as the one in my behind right now, a medium, which was larger and wider, and a large, which to me looked very big. To me it looked too big for my little butt, for sure.

"Remember, you agreed to do anything and everything that I ask you to do?"

"I remember. And yes, I'm still wearing the ankle bracelet. What now?" I probably sounded just a bit exasperated.

"Go ask that woman if they have any good forced feminization videos or popular pegging videos?" The other store clerk, a woman, was stocking and sorting the video offerings.

So, submissive Mattie went over to her. "Ma'am, where are the forced feminization videos and pegging videos? And can you show me if there are any popular ones?" I must have been 50 shades of red. I could feel myself flushed and I started to sweat.

"Sure, come on over here." I wanted to crawl under a rock and hide, but I followed her and took two videos that she recommended.

Strap-on, butt plugs, and videos in hand, I went back to Diamond, who now had two toys, a vibrating wand of some kind and the vibrating dildo I had seen earlier.

"I think that's all we need. Let's go check out."

We got over to the checkout counter and put things on the counter to pay.

"What are those videos, Mattie? Let me see them?" So I picked them off the counter and gave them to her.

"We don't need these. Mattie. You're so silly." Turning to the salesman, she said, "I've got to watch him sometimes. Really. I hope you don't mind, we won't be getting these." I felt about three inches tall. As the guy rang everything up, I couldn't get out of there fast enough. The fact that all the stuff cost a lot of money was irrelevant. I just wanted to get my embarrassed self out of there ASAP.

The taxi was waiting where we left it. We got in, and it being just a short distance, arrived at our hotel in a few short minutes. 


Once up in the room, we had talked earlier about going out to eat, but Diamond said she changed her mind and wanted to stay in and play, so we ordered a pizza and some Pepsi Lights. Diamond retrieved a bottle of water from the refrigerator and handed it to me with another blue pill. "Time for your vitamin, Mattie girl. The fun is about to get started."

We spent the next two hours trying on outfits, pajamas, panties, eating our pizza, and just generally having a blast. We shared giggle, laughs, smiles, and fun of being with someone special. We critiqued how each of the things we bought fit and looked on us. She said I looked just too cute in tie-dyed sports bra and leggings, and as was the case with almost all our purchases. Her bottom looked every bit as spectacular as I had imagined in her bodysuit, which, like my tie-dyed exercise outfit, fit perfectly. She took a lot pictures and lots of selfies of us together. She must have took 50 or 100 pictures in all.


"Mattie girl, do you want to help me play with my new toys?" she asked playfully.

"Diamond, you KNOW the answer to that question."

"Well, okay then. Get out the middle sized butt plug we bought tonight and some lube. Take the little one you're wearing out and put the new one in while I get ready."

I went onto the bath to swap plugs. When I came out with the new plug in, I found her on the bed, a dildo in one hand and the wand style vibrator in the other. She turned on the vibrator and started going back and forth over her pussy and clit.


"Take your panties off, sit right here and watch me. Do NOT touch yourself. Your fun comes later. Much later."

When she felt like she was wet enough, she started probing her lips with the dildo, and slipped the head inside her.

"Come closer and help me. Take this and move it on and out of me, very slowly. Nice and easy."

She arched her back a little I took hold of the dildo by the balls at the base, and started sliding it into her. Simultaneously she continued rubbing the vibrator on her clit, back and forth, back and forth and I slowly worked the dildo in and out, in and out. I was nearly hypnotized watching the dildo penetrate and then pull out of her pussy, even though I was doing the pushing and pulling, and watching her perfectly manicured hands work the vibe on her clit.

"A little faster, Mattie girl, a little faster."

I increased my tempo just a little and at the same time Diamond turned to vibrator up to the next level. Almost immediately she started squirming in rhythm with me fucking her with the dildo.

"Faster! Faster! It feeeeeels sooooo goooood!"

I was thrusting it in and out of her at a perfect pace. Her breathing was heavy and she began sighing and moaning.

"Thisssss feeeeels sooooo, sooooo gooooood! I am cumming! Oh oh ohhhhhhh!"

The waves of orgasm swept over her like a tsunami. She was flooded with her sweet wetness. The dildo slid in and out of her with saturated ease. Her orgasm was long and powerful. I could feel her pussy spasming on the on the dildo, almost squeezing it out of her. I kept it in and started to slow the stroking motion. As her orgasm subsided, she took the vibe away. I was thrusting tantalizingly slow by then. Just enough to let her come down slowly, at her own pace.

"That was so strong. So good. I need a break for a couple of minutes, and then you'll get your reward."

"Reward?"

"I'm going to make sweet love to your cute white ass with the new strap-on you picked out. You are going to love it. And so am I! You've been such a good girlfriend, letting me make fuck you is one thing, but I'm going to make sweet love to you while you submit to my 'cock'. Are you ready for me to take you?"

"I'm more than ready, Diamond."

After a few minutes break and a cool drink, she put the new strap-on onto her torso like she'd done it 1000 times, grabbed the bottle of lube, and directed the next action. "Go into the bathroom and take out the plug. Take off your panties and then get up on the bed, Mattie girl. On the bed, I want you to get down on all fours, and be ready for me."

I climbed up onto the bed and 'assumed the position'. She came up beside me and playfully smacked my ass once on each cheek. "If you were my permanent sub I would have so much fun with you. How much fun I'd have to beat this little ass red!""

"I'm sure you would. And I'm sure I'd be in heaven. I'm really into you, Diamond. You know that, don't you?"

"I know you are, Mattie. I know you are."

She started applying lube to my bottom, gently, but efficiently.

"I'm using plenty of lube so my special new girlfriend will enjoy having me make sweet love to her ass as much as I will enjoy doing it."

I felt gentle pressure on my bottom as she began to push it into me.

"Relax, Mattie girl. I'm not going to hurt you. I've done this before."

"You did it to me once before, the last time I was here, remember?"

"This is different. That night I fucked you. Tonight I'm going to make love to you. Relax and feel me in you. Tell me how it feels."

By that time she had slid it slowly almost all the way into my bottom. "It feels really good, Diamond. Really good. Don't stop."

I won't. Just relax and enjoy. Feel me pushing in and pulling out of you. Feel my hands on your hips holding on to you. Feel me stroking you so deep in that cute little ass of yours."

"It feels so good, Diamond. Feels so, so, good!"

She made love to my behind in the most remarkable, wonderful way. I could feel her moving in and out and in and out, over and again. But it was never hurried, violent, and aggressive. It felt amazing.

"Are you ready to cum, Mattie girl? Are you ready? You've been such a good girl tonight. Today and yesterday, too. I know you want to cum badly, don't you.?"

"Diamond, you know I do."

"She pulled out of me and told me to roll over on my back.


Taking yet another new pair of soft, satin like material pink panties in her hand, she wrapped them around my fully erect cock and started a very slow stroking motion. She was still wearing the strap-on.


While she lovingly stroked me, p and down, up and down, we had a beautiful conversation about our friendship, and about this experience. It felt so good. We each told each other which part of girls day was our favorite. I told her that mine was the night before, when I first saw that she had laid out the the pink panties and found out she was making my girls day fantasy come true. She said that her favorite part was a tie between taking selfies in the lingerie store dressing room with my dick sticking out of the top of my panties, and shopping for sex toys, the look on my face as I asked all the questions she told me to ask the employees. She said she loved seeing me so red from embarrassment.

I told her I was going to cum soon if she didn't stop. But rather than stop, she tightened her grip and increased her tempo. After the day I had, it didn't take long after that. I felt it coming on. "I'm going to cum! I'm going to cum!"

"Let it all out, Mattie girl. Let it all out."

I did. When I came it was very powerful, incredibly so. All the pent up sexual energy from such a fun and exciting 24 or so hours came to a climax that was worthy of my excitement.


"I had so much fun with you, Mattie girl. I want to go shopping with you again. But next time I want to be your Domme, not your girlfriend. Won't that be a lot of fun, too?"

Then we spooned in bed in our new pj's and watched a movie. I asked her, "Can I be the small spoon? Please?"
 I loved the feeling of safety and peace there in her arms. She may be tiny, but she makes me feel safe and loved. We lay like that, tired and contented, until we fell asleep.

Sleep found me, but not too quickly as the events of the past two days ran through my brain. Diamond was asleep in no time. We slept in late in the a.m., as my flight wasn't until mid afternoon.

When we woke up, we took turns in the bathroom, and I asked Diamond for one last favor. "Diamond, you know how much I love to eat pussy, and you know I think that yours is amazing. Would you sit on my face and fuck my face one last time before we get ready to go? Please?"

She wasted no time pulling off her panties and mounting my face. I had a perfect view up her torso at the perfect, chocolate candy colored nipples on her perfect breasts, and her pretty face, with her sensuous lips and piercing eyes. She looked down at me and smiled as she started a slow ride. Her sweet pussy moved slowly across my mouth and my nose as she started slowly rocking. I licked and kissed her sex. I was in heaven. I don't know if I was showing her my gratitude, my affection, or pure lust for her, but I've never felt so connected and so happy to be doing just what I was doing, my favorite thing, being used by an amazing, powerful woman I adore as her sex toy and pleasure outlet. Her grinding slowly increased in both pressure and tempo. She was wet, really wet. I inhaled her sweet aroma as I licked her lips and clit hungrily each time they passed. Each time she rocked backward, I could feel her clitoris flick against my nose than lips, and each time she rocked forward, I could almost lick her little brown rosebud of a booty hole.

Diamond can go and go, and with her being in full control of both the motion and intensity of my oral ministrations, I could see the pleasure mounting on her face and hear it in her moans and groans.