Sissy Diary Pt. 02

Disclaimer/Author's note: Everyone in this is 18+ and consenting, and this is completely fictional. Please send me any comments or feedback you have. I appreciate any encouragement you've got. I hope you're enjoying this.

___________________________________________________________

As always, I did as I was told. I returned to the kitchen and began to bring out the food that I had cooked for Ms. Angela and Mary for brunch. I also brought out the mimosas, which I knew would likely be the most important part of the meal, based on what Ms. Angela had told me about Mary. The two women talked and began to eat, paying little attention to me. I made sure to tidy up when any items were finished, but otherwise I stood at attention waiting for some direction from my miss. I made sure to keep the drinks refilled, as Mary outdrank my mistress by more than double. Her cheeks were a little pink by the time she talked directly to me.

"So cutie," Mary said, staring right at me, "You've been a good girl serving us and not interrupting, but I think it's time that you get a little attention, does that sound good to you?"

I couldn't help but blush excitedly as I replied, "Yes, miss, thank you, miss."

Miss Angela laughed, and Mary grinned wickedly, which made me feel like I'd been a little too eager in my response. Mary looked over at Miss Angela, "So she's trained to do everything, right?"

"Yes, though she can refuse, of course," Miss Angela said. She looked at me and I felt a sense of warmth. For all the control Miss Angela had over me, she always treated me with respect and decency.

As I looked back at Mary, she was standing up and sliding her yoga pants off. Then she took her top off. Mary was in incredible shape, her muscles fit and toned, everything appearing to be chiseled from marble. She had on a rather striking set of black lace lingerie. The panties were the kind that created a deep V plunge that only accentuated her figure. I stared awestruck at her as she continued to strip until she was naked in front of me. Her breasts were smaller, maybe only a B cup, but they were very perky, nipples excitedly pointing out at me.

Mary stepped over to me, getting right up to my face so I had to look up slightly at her. Even with my heels, she was a teensy bit taller than me. "Angela says you'll do anything I ask you to do, is that right sissy?"

I couldn't help but bite my lip a little to try and prevent a moan. I nodded as I tried to keep my composure. I could feel my cock pushing hard against my cage in anticipation of whatever was coming next.

"Well, I've had a very stressful week, and I could use some relaxation and release." Mary's hand began to run along my skin. She started from my hand and traced up and along my shoulder before grazing my neck. That's when I couldn't help it, and I finally let my moan out. Mary seemed pleased by this because her hand then went down to my nipple. Her fingernail circled enough to excite me, teasing me before she gave my nipple a pinch. I shuddered a little; it was such a thrill to have another woman touching me. "Oh, you like that, don't you? You like it when I'm a little rough with you?"

"Yes, Mary," I mumbled out. I admit, I did enjoy it. There was something pleasurable about the moment of pain and then the release from it.

"Well, let's inspect you then. I want to look you over and see exactly how good a job Angela has done with you." Mary took my hand and made me follow her as she sat back down. She turned her chair to face me and began to give me directions. "Give me a twirl, I want to see the full 360 view. I spun around as I was told. I blushed, knowing that my twirl would have brought the skirt up enough that my leaky panties must have shown. When I stopped, Mary began to tease me. "Such a naughty sissy, I saw that wet mark in your panties. You just can't help yourself, can you?" She motioned for me to come closer, and I obeyed. Mary reached under my skirt and touched the wet spot on my panties. She pulled her hand back, and I could see the sticky liquid on her fingertips. "Now look at the mess you've made of my nails sissy. Don't you think you need to clean it?" She held her hand up high, and I knew exactly what she wanted. I leaned down a little and took her fingers in my mouth. I licked and sucked her fingers clean, tasting that salty and slightly bitter taste of my excitement.

"Good girl," Mary said as she pulled her fingers out of my mouth. "Now it's your turn to taste me." She slid forward in her chair and spread her legs, exposing her pussy fully to me. I began to kneel, having to brace myself on the table a little due to the stilettos I was wearing. "Still getting used to your big heels sissy?" Mary teased. She looked over at Miss Angela, "God, I love it when they're still learning, that little bit of hesitance and embarrassment is such a turn on."

I slid forward on my knees until I was right in front of Mary's pussy. This was the first pussy outside of Miss Angela's that I had seen in quite some time and only the second since I became Sammy. I paused for just a second, deciding whether I should tease or go right for Mary's clit. That pause was plenty for Mary as she grabbed the back of my head and pulled me in. "Don't be a shy sissy, just lick." I did as I was told. I began to lick at Mary's clit as I had been trained to do. Ms Angela had taught me how to pace, how to build up, and just how to lick to best give the woman pleasure. I tried to remember everything I was told. It was a little hard to focus so much as I could feel Mary's hand still pressed on the back of my head. My nostrils filled with Mary's scent, the pheromones making my heart beat faster. It was absolutely intoxicating being held into such a magnificent woman's pussy like this. I could feel Mary twitch, her hand gripping tighter into my hair as I brought her closer and closer to the edge until she finally came. She moaned loudly and yelled, "Don't stop!"

I kept licking, pushing the pace, trying to get Mary to come until I was panting hard and my jaw was beginning to tire. Finally, I built up to one last, large finish. As I began to feel Mary's orgasm, both her hands grabbed the back of my head and pressed my face up against her as she came, squirting a bit right into my mouth. I tried my best to swallow it all, to get every drop I could, but I knew I was covered in it and there was nothing I could do about that.

Mary's hands let go, and I leaned back into an upright kneeling position. My heart was racing, and I was just trying to catch my breath and rest my jaw and tongue. Mary sat, slumped in her chair, panting, which to me said I had done a good job. I looked over to Miss Angela, who was grinning from ear to ear. "I'm so proud of you, Sammy," she said. "I admit I was a little worried that you'd be too shy when I brought my first friend over, but you are well on your way to earning that surprise tonight." I bit my lip as my heart fluttered a little; whatever that surprise was, I wanted it so badly. "That said, Sammy, you do need to clean up. Mary is quite a mess right now."

I looked back at Mary and saw the liquid from her squirting on the base of the chair and a bit on the floor. I was so intent on getting that surprise that I didn't even hesitate. I leaned forward and began to lap up the liquid on the floor. Fortunately I keep the house incredibly clean and had just washed the floors yesterday, though I don't think my overly horny mind even paused to think about that. After lapping up the little bit of liquid on the floor, I leaned back toward Mary and did the same to the chair. I admit, I loved the taste. It was different, but still similar to when I got Miss Angela to squirt.

I gently lapped up the last, barely grazing Mary's skin as I tried to clean her too. She moaned again and looked down at me. "God you are such a good sissy." She sat up straighter, still maintaining her eye contact with me. "Sadly, though, I ruined your cute makeup. I know you must have worked so hard on that; you did look so pretty." Mary looked over at Miss Angela. "Well, we can't have her spending the rest of the day looking a mess like this, can we?"

Miss Angela laughed, "No, of course not, she'll have to get cleaned up to serve us the rest of the day. She'll need to change clothes, too. It's a shame, though, I have enjoyed the pink maid outfit."

"So have I," Mary replied, "But then again, I wouldn't mind seeing Sammy in some other outfits. After all, if I'm going to be spending more time with her, I'd like to know that she has an outfit to meet whatever need I have."

"Oh, I can assure you she does," Miss Angela replied as she stood up. "Soon enough, she might have more outfits than I have. Would you like to pick what she wears next?"

Mary grinned, "Of course, that sounds like fun."

"Well then, Sammy, you head to the bathroom and begin to clean off your makeup, run a bath while you're doing that. Then Mary and I will be in once we've chosen what you'll wear."

"Yes, Miss," I replied as I stood back up. I wobbled just a little as I got back to my feet, which Mary enjoyed. I felt a firm smack across my ass as I began to walk.

"Don't worry sissy, I'll pick a pair of heels to match whatever outfit I put you in," Mary teased.

I walked down the hall and did as I was told. The main bathroom had a large jacuzzi-style tub, which I began to fill with warm water. I put in a small amount of liquid to make the bath sudsy and bubbly, since I felt that always made it more luxurious. I then sat at the stool next to the sink and began to remove my makeup. This was always odd for me, as the makeup had gotten to the point where it just felt like a natural part of my face. Without it, I felt a little naked and not as much in a fun way.

Around the same time that I finished cleaning off my makeup, Miss Angela and Mary came into the bathroom. Mary, still naked, had a hungry look in her eyes and a smile on her lips. "Now let's get both of us nice and cleaned up so that you can put on the outfit I picked out for you. I think you're going to like it. I know I will."

Mary took off her jewelry and placed it on the counter, then tied up her hair before she stepped into the bath. She slid down so the water was just covering her breasts, her shoulders, and above still sticking out. "God, this feels so nice. Warm, bubbly, and relaxing. Though there is one part missing." She looked over at me, "Come on now, get in sissy."

I looked at Miss Angela, "Miss, may I get in the tub with Mary?" I asked.

"Of course you can, Sammy," Miss Angela said as she stepped over to me and began to help me undress by unzipping my maid's outfit. She tied my hair up and sensually took each piece of clothing off of me, not letting me help at all. Mary sat in the tub, clearly enjoying herself as she bit her lip while watching. At last, Miss Angela took the key from her necklace and unlocked my cage. "You made such a sticky mess. You'll need to clean yourself, and I'll need to clean the cage."

I stepped up and into the tub, on the opposite side of Mary. The warm, sudsy water felt nice on my skin as I slid in. I relaxed for a moment before I felt Mary's legs entangle with mine. She began teasing me, her bare foot gently grazing my cock and balls, which made me shudder and moan.

"Oh, is that too much sissy? Has it been too long since you've cum?" she ran her toes along my shaft and I shuddered.

"I cum whenever Miss Angela wants me to and that's plenty," I said defiantly. That said, it had been almost a week since Miss Angela had let me cum, so I was a bit sensitive. My balls had felt achy and full for the past day or two, and they certainly had felt full since Mary arrived. Mary continued to tease me as I looked at Miss Angela, who was rinsing my cage off in the sink. I didn't want to betray Miss Angela, but I felt like if Mary kept this up, I was going to spurt in the tub.

Mary seemed to know this as she pressed further, "You know what, I want a little more, this tub is so big, but I just want to feel you better, come over to this side so I can feel your body on mine," Mary grinned wickedly and I knew this was just so she could tease me further. Despite this, I did as she wished, because I was determined to be a good hostess and make Miss Angela proud. I slid over and sat on Mary's lap inside the tub. She wrapped her hands around me and pulled me in close, pressing her body right against mine. Her warm, soft skin felt wonderful. I couldn't help but enjoy the feeling of her perky breasts pressed against me.

Somehow, this is what my life has become. I had a gorgeous Miss who I adored, who was now sharing me with this fit goddess of a woman who was now teasing and tormenting me. Mary's hands touched me all over before settling on my cock. I was already hard, but the feeling of her fingernails dancing along my skin made my heavy balls ache and strain. My heart was racing. I could feel Mary's breath on the back of my neck, and it made my skin tingle with electricity. She licked my neck and began to whisper dirty things.

"I know you're supposed to get a surprise if you're a really good girl today, and I even know what the surprise is." Her hand wrapped around my shaft and worked slowly up and down. "I also know that if you cum you don't get the surprise." She stopped stroking and instead gave my balls a light spank, which made me moan and shudder. "So I'm going to make this day awfully hard on you. I won'; t force you to cum, but I'm going to tease you, touch you and torment you as much as you can, so that if you do make it to the end, you've really earned that surprise. Do you think you can make it sissy? Do you think you'll get your big surprise or do you think you're going to end up squirting your cum right here and now?" Mary then slipped a finger in my asshole, I bit my lip to stop from crying out in pleasure. My cock twitched and I could feel myself almost lose it right there.

To Be Continued...