I somehow managed to avoid the trap of asking, “What’s wrong?” Instead I asked for permission to speak and when she granted it, I said, “Mistress Hannah, it is pretty clear that you are struggling with some decision. Is there anything I can do to ease your mind or help you in any way?” To my surprise, she started to sob. Then she turned to me and ordered me to turn on my side with my back toward her. She began to fondle my panty covered ass and then she started to talk.
“We’ve fulfilled all of the fantasies in your stories plus some of mine. There’s one more fantasy that I want us to fulfill. It’s one of my personal fantasies and I’ve scheduled it for tomorrow, but I’m very scared. I’m hoping that you had this fantasy but just never wrote about it, or at least that you’ll participate and be okay with it later. I want to start raising children and I know you want to also, but I’m afraid that if you don’t want what I have planned for tomorrow it will destroy our marriage whether we go through with it or not. I can cancel it because I love you too much to lose you, but that might be even worse because this is really important to me.” As she had said all of this, her other hand wandered in front of me and began to caress my cock through the soft satiny fabric covering it. “This will be far more humiliating for you than anything I’ve required of you.”
I’m sure she felt my cock jump as she said that, but I continued to listen as it grew and she continued to speak. “You are a special man and I don’t want to lose you. When we first met, I was so disappointed with our first attempts at sex that I almost gave up, but Bella told me that you sounded like just the kind of guy who would eventually please me more than any other. I’m glad I listened to her because that’s just what you’ve become. But now that you’ve become as much of a man as we could make you, I need you to be more of a sissy than you’ve ever been. Then I’ll know that you’re the man I want to raise my children with. The problem is that I can’t tell you what my fantasy is without ruining the surprise for you and that is part of the fantasy. So I’m afraid that I have the fantasy I shouldn’t have and that I will hurt you or me too much either way.
By this time, my cock had grown to full size and become quite hard. I had already come earlier that evening, but I was sure I could come again in any way that would please her. There actually was another fantasy that I had entertained, but I never had the courage to write about it, both fearing and hoping that writing about it would make it inevitable. I dared to hope that it was the same fantasy and I dared to offer the way out of her dilemma. I asked for permission to speak again and she granted it.
“Mistress Hannah, please know first that I trust you and love you more than I could ever imagine trusting or loving anyone else. Knowing that you want to keep me around despite my inadequacies, I cannot imagine denying you anything. I cannot imagine that any other woman that I might find and who would accept me as the slave I am, would be as bothered as you are with the possibility that I might not want to fulfill something that she would require of me. You have done more for me than I have deserved and that buys you a free pass to use me as you wish. What am I? I am pathetic. What am I not? I am not useless. I have reveled in every opportunity to please you. I make the choice now, without knowing what you have planned. I will serve at your pleasure tomorrow.”
“Oh, thank you slave,” she said as the tears once again streamed from her eyes. With that, she let go of my hard cock, rolled over and was soon breathing the regular breath of a sound sleep. It took a while before I could sleep after that. I was very nervous about the next day.
Mistress let me sleep until 8:30, but when she woke me, she told me to have a light breakfast and then shower right away. To my surprise, she then had me dress in male clothing over my original pair of her pink panties with a fairly small buttplug inserted. She grabbed a small duffel bag and we drove to the piercing parlor where Mistress Amy showed us into a private room and locked the door behind us. I was happy to see Mistress Amy again because I enjoyed her bubbly personality. The fact that she was short, blonde, rather voluptuous and tattooed possibly from her elbows to her knees also helped. Mistress Hannah told me to drop my jeans and of course, I got hard when Mistress Amy giggled at my panties. Then Mistress Hannah told me to drop my panties. When they were down at my knees and I stood straight up, Mistress Amy looked straight at my dinky winky and then up into my eyes and back down again. Needless to say, she did not look favorably impressed. She sat on a work stool right in front of me and asked Mistress Hannah what kind of art she had in mind.
“As you can see, he’s pretty pathetic as a man. He makes a much better sissy-boy, so I’m planning something special for tonight.” She gave Mistress Amy a slip of paper and then said, “But before we get to that, I would like this permanently tattooed right here,” as she slid her finger right across the space above my cock where my pubic hair grew. “He made a commitment to me and if he breaks it, I want that to be a reminder. I want it to just be simple, like a sign on a fence. I don’t want him to see it while you do it. I assume there will be a bandage on it for a few days?”
Mistress Amy smiled and said, “Yes, we can cover his eyes while I do it and then it will need to be covered by a big gauze pad until Tuesday. Anything else?”
“Yes, I would like him to have a temporary tattoo in vivid colors that looks just right in the doggy position. Here’s a photo of what I’ve done in the past with a marker. It needs to be ready for tonight. Can you do something that won’t rub off for a few days?”
Mistress Amy looked at the photo and snickered. Then she assured Mistress Hannah that if an airbrush and stencils were okay, I could be stained and on my way in about two hours.
“That’s good, Amy. This will be easier if you order him around as necessary. You can call him Michele or slave if it pleases you.”
I’m sure that Mistress Amy noticed that my cock was now straining from all of the humiliation, but she did not hesitate to take charge. “Turn around slave, I need to see your ass.” With my jeans around my ankles and my panties around my knees, I shuffled around and bent slightly so she could see. The mistresses then spent about ten minutes discussing design details until they had a plan for what Mistress Hannah wanted. After making some stencils with a machine and getting her supplies ready, she had me pull my panties back up and lay back on an angled table. Then she pulled my panties down so that just the base of my tiny cock was exposed and she laid a small pad for stabilizing her wrist right on it. Then she covered my face with a towel.
The tattooing was painful and took about an hour. She kept moving her hand around so I couldn’t tell what design she was putting on me. When that was finished, she pulled my panties back down to my knees, taped a bandage on the tattoo and had me readjust to the doggy position with my knees on a thick cushion and my body draped over a padded adjustable table. She wanted me to keep my weight on my knees as much as possible so my back would be properly arched, but I was allowed to shift it to my chest and abdomen when she wasn’t spraying the stain on. Sometimes as she worked, she bumped the buttplug with a finger or other part of her hand and this kept me pretty hard the whole time.
When the ass tattoo was done I had to remain bent over for another 15 minutes so Mistress Amy set a timer and then asked if I would mind if some of the other girls who worked there came in to see her work.
Before I could answer, Mistress Hannah said, “Whether she would mind doesn’t matter.
I prepared to get up when Mistress Hannah pulled something out of her duffel bag and asked Mistress Amy if it would be okay to give the art work a more strenuous test. “And it would be a big favor to me if you would rate his pussy licking skills while I do.”
Mistress Amy giggled and said, “Well, I have to admit that this job has made me pretty wet.” She locked the door again, and watched as Mistress Hannah handed her strapon to me and took her jeans and panties off. Mistress Amy’s eyes got huge and I noticed that she licked her lips when she saw Mistress Hannah’s erect clitoris.
I strapped the dildo on Mistress Hannah and then Mistress Amy dropped her shorts and noticeably wet panties and sat up on the table spreading her legs for me.
As Mistress Hannah pulled my buttplug and pushed her favorite dildo into me from behind, I kissed my way down Mistress Amy’s tattooed thighs and into her juicy slit. It wasn’t easy, but I found her clit in a forest of thick brown hair and piercings. I did my best to avoid being distracted as Mistress Hannah grunted and did her best to hammer my ass-art with her thighs. Mistress Amy was soon moaning and quickly came to a very satisfying orgasm. When she eased her way out from under me, she said that I was almost as good at licking pussy as her best girlfriend and much better than her best boyfriend.
Mistress Hannah abruptly pulled her dildo from me and announced that she was satisfied there would be no smudging, but I think she could tell that I kind of liked Mistress Amy, so she said, “I would be glad to let Michelle strap this on you Amy. It actually would be another favor to me.”
Mistress Amy hesitated a little and then said, I actually have a strapon that I’ve never used. It’s a little shorter and a little fatter. It’s out in my car. Would that be okay?”
“Why sure sweetie, go get it.”
Mistress Amy left her panties on the chair, pulled her shorts on, dashed out the door and returned in just a few minutes with a small shopping bag. She relocked the door pulled her strapon from the bag and said, “Michelle, meet Average Joe. He’s exactly the length and thickness of an average cock. Whenever one of my boyfriends wants to fuck me in the ass I tell him that he can after Average Joe fucks him in the ass first. I’ve had him for two years and five boyfriends and he’s still a virgin.”
I knew what Mistress Hannah expected of me so I didn’t wait for a command. “Please Mistress Amy, allow me to strap him onto you and then fuck my ass with Average Joe.”
She handed him to me and dropped her shorts. As I strapped Average Joe onto her, she slipped a little dildo that dangled beneath it into her pussy and then peeled off her sleeveless shirt and bra. Of course her nipples were pierced, one vertically and one horizontally, and her navel had a ring also, but the tattoos on her full breasts were stunningly beautiful. She stepped behind me and Mistress Hannah dabbed a little gel on the tip of Average Joe as I leaned down onto the table again. Mistress Amy is shorter than Mistress Hannah, so I had to spread my legs a little wider, but I soon felt the cold gel pressing into my ass.
Even though Average Joe was a little thicker than Mistress Hannah’s cock, it was not the largest thing that my ass had taken. Mistress Bella’s strapon and several of my buttplugs were larger. I felt comfortably stretched, but despite her small size and easy going personality, she forced AJ fully into me and began pounding my ass pretty hard.
“Fuck, fuck, fuck, this is fun. I’m fucking a guy’s ass. Unh, unh, unh. This is good. I can come again. I’m fuckin’, unh, a sissy-boy’s ass. Fuck you Michelle, fuck you Michelle, unh, unh, unh. Oh, I’m coming, ohh, this is good. Ohhhhh! Ahhhhh! Ahhhhhhhhh, ahhh, ahhh, ahh, ahh.”
When she pulled Average Joe out of me, she said, “Thank you Mistress Hannah for letting me fuck Michelle’s ass. Um, has he… I mean has she earned a reward?”
“What do you have in mind, sweetie?”
“Well, um, Average Joe’s not a virgin anymore and his… Um, I mean her dick is so dinky it doesn’t look like it will hurt me and uh, I am an anal virgin and I’m kind of curious and uh, I noticed that you have a really awesome clittie and I would love to lick it.”
Mistress Hannah actually blushed a little and replied with, “Normally I wouldn’t even consider that, but you’re such a sweet young thing, how can I say no? You may lick me while Michelle fucks your virgin ass, providing she keeps her pants around her ankles and her panties around her knees.”
She didn’t have to give me permission twice. I backed away from the table and despite the fact that I had been kneeling on a cushion for hours, I was happy to kneel for a few minutes more. Mistress Hannah sat up on the table and Mistress Amy gave me a condom. Then she adjusted the cushions and leaned over the table.
I put some gel on my finger as Mistress Amy began to kiss and lick Mistress Hannah’s inner thighs. As I turned to look at Mistress Amy’s ass, I was awestruck by all of the beautiful tattoo art from her shoulders to her ankles. She didn’t have a tramp stamp, she had a color-filled undulating sensual mural. I eased my finger into her tight hole with no difficulty and teased it a little until it opened fully for me. When my condom-covered cockhead slipped in, she gave a little grunt, but continued licking Mistress Hannah’s slit.
Mistress Hannah began to moan as my cock reached full depth in Mistress Amy’s ass. Mistress Amy began to lick and suck the biggest clit she’d ever seen as I began to stroke into the round globes of her ink-stained ass. I didn’t pound her hard, because I didn’t want to bump her face off her little tongue toy. I stroked into her, using every trick I had to last as long as I could. The pain from the fresh tat probably helped.
When I heard the distinct tones of Mistress Hannah’s impending orgasm, I picked up the pace of my thrusts into Mistress Amy’s ass. I noticed then that she was rubbing her own clit and pinching one of her nipples with her fingers. She was also making little muffled wimpering sounds as she increased the pace of tongue tickling on Mistress Hannah’s clit.
I started to come and that triggered Mistress Amy’s orgasm and then Mistress Hannah went over the edge with shudders of uncommon ecstasy.
When we all finished panting, I eased my cock out of Mistress Amy’s non-virgin ass and Mistress Hannah said, “Oh sweetie, you can really lick pussy. Thank you, Amy, and thanks for all you’ve done for Michelle.”
“My pleasure Ma’am.”
The mistresses dressed and settled up the bill and then Mistress Hannah offered Mistress Amy the honor of ordering me to cover my pathetic cock for the sake of the public. Mistress Amy giggled and said, “Pull up your panties and jeans and hide that teeny weinie, Slave Michelle.”
Before we left, Mistress Hannah reminded of my last obligation to Mistress Amy. “Thank you Mistress Amy for the beautiful body art and allowing me to lick your beautiful pussy and for fucking me in the ass with Average Joe and for honoring me with your anal virginity.”
“And?”, inquired Mistress Hannah. I quickly thought back over what we had done and what I had appreciated.
“And for being honest and direct about how tiny my cock is.”
Mistress Hannah nodded her aproval and Mistress Amy said, “I enjoyed all of it Michelle. Thank you Mistress Hannah.”
As we drove home, I thought about my ass-art and dared to hope that Mistress Hannah had the same plans for it that I had fantasized about.
