Pictures Tell the Story Pt. 06

This story is about Non-consensual anal sex, bondage, crossdressing with a twist, and mild BDSM. If this is something you're not interested in, don't read. If it is, I hope you enjoy my story. Any suggestions or comments are welcome.

Chapter 6, Bobby's little girl returns.

Saturday night went way beyond what I expected. The removal of my gag, the chance to test my voice emulator, and the team working in concert with my instructions making the experience so much better than I expected. All in all, I had a wonderful time.

Although only nine of the team had returned, they still managed to have me three times each. Eight cups of cum, down the hatch, and several were introduced to my mouth and tongue. We said our farewells, and I explained that it might be a while before I could do this again.

They were sad but understood. I got up immediately after they left, cleaned up, dressed, packed, and hiked back to my car. I drove home drinking my special coffee and decided to save the sandwiches for later. I arrived home, took a shower, and smoked a bowl.

I left things packed and called Bobby. She was happy to hear from me so soon. I said, are you free today? Not free but reasonable what do you have in mind? She replied? Anything you want, I said. She giggled and said, when? I replied, give me about half an hour.

She said, be on time. I replied, never. She giggled, see you soon. I called the wife, chatted a bit, said, love you, and talked to you tomorrow. I double-checked to make sure I had everything then headed out to Bobbies.

The garage was open, so I parked and knocked. She came to the door and said, you are late again. Little girls must learn to mind. We will take care of that in a while. She giggled then said, come in and make yourself comfortable. I thought you were busy this weekend.

I told her I had decided to cut it short and be with you today if you will have me. I don't have to be home until tomorrow morning. She said, wow, I couldn't be happier and gave me a long kiss. She was dressed in a short skirt and blouse. She looked radiant.

I told her I hadn't had a chance to wash my clothes; I hope you don't mind. She said I am sure they are not really dirty, just worn a little; it would be ok. I told her I would have to return to the shop and get something new and exciting to wear for her.

She said, no need; I picked out a cute outfit just for you for being such a good little student. I told her I could hardly wait, I trusted her taste when it came to all things clothing, especially when they were for me.

She told me I was sweet to say that. I told her if I were not married, I would work hard to be hers every night. She said, if that should ever change, she would love to have me. That for now, she would be happy to see me when she could.

She continued, I am so lucky that fate stepped in and brought you into my store. It was meant to be. I said I think that myself. You make me feel giddy in anticipation just thinking about you. My mind was on you all weekend.

I said I wouldn't be surprised if she had an unexpected orgasm on Saturday, then laughed. She said, nope, but I plan to make up for that several times over. See what happens when little girls talk dirty? I said I would, I'm sure.

She asked if I wanted anything to eat or drink. I asked for some coffee and maybe an orange juice if she had any. She said, are you sure you don't want to eat? I said I didn't want to risk being dirty during our play.

She said, if that happens, I know how to take care of that, so don't worry. She continued, I will fix you some eggs and toast. You need to keep your strength up; you look tired. I replied, that would be awesome; I am hungry, actually.

We ate breakfast together. She said I told you we would eat together, remember? I replied, yes, thank you. We lounged around and finished off a pot of coffee. I was beginning to wake up. Being close beside her and smelling her scent gave me a hardon.

We casually chatted about my work, shop, where my wife was, and just general subject until noon. She said, shall we go to the bedroom and get dressed? I said, sure, but would you mind if I wear my blue choker with my new outfit? She replied, sure, sweetie.

She undressed me and scolded me for having a hardon. I said, sorry, it's all your fault. I placed the chocker on. Do you know what happens to dirty little girls? I replied, everything. The voice emulator had the desired effect.

Her eyes got big, she grinned and said, oh my god, did you do that for me? I replied I thought it would be propper to sound female since you refer to me as your little girl. She said that must have cost you a fortune. I replied, if it makes you happy, it was worth it.

She said, well, it does, little girl. I am so proud of you for going so far as to please me. I smiled and said, anything for you, Bobby. She said I am going to make you squeal with pleasure. She removed her clothing, and for the first time, I saw her completely naked.

Her breasts were a little larger than my wives, but they were well-formed and natural. Nice plump nipples. I sat on the bed as she slowly turned to show off her nice ass; she bent over, giving me a perfect view. I could barely see her anus; it was small.

No blemishes, moles, hair, freckles, or scars, she was a perfect female with a lurking monster between her legs, her balls were a double hand full, and they looked filled to bursting. She said, see anything you like. I told her she looked delicious. She giggled.

I said I see nothing that I wouldn't lick, suck or stick my tongue and dick in. She said, now, be careful. I said, I know you're a top, and you know I am a bottom but, if I were to switch hit, I would want it to be with you. Punish me if you want, but. She giggled again.

She said, there is no harm in dreaming, little girl, as long as you understand, some don't come true. She said, lay back on the bed; she knelt and starting sucking my hard cock. I was moaning and whispering to her in my sexy female voice to keep going.

She didn't stop until I filled her mouth with my cum. She smacked her lips and said, delicious. You are a tasty little girl. I think I will keep you. Let's get you dressed up, sweetie. She left and returned with the outfit.

It consisted of a pink training bra with tiny nipple holes, a pink and white silk skirt with white suspenders; it hung just above my crotch, crotchless pink and white panties, and pink knee socks. She finished with pink slippers. She laced them up.

She forced my nipples through the holes, and the tightness made them swell almost as much as my enlargers. She inserted gold medium gauge nipple rings, a gold chain, and a gold four-inch penis in the middle. All were heavy. The bra lifted, and the gold pulled down.

She left me alone to go and get dressed; while she was gone, I smoked another bowl and was stoned by the time she returned. Once again I was stunned by her appearance. There was no doubt she was a Mistress. Her outfit screamed domination. White leather everything.

There was a black leather whip hanging from her hip; it had long strands knotted down the length. My ass got goosebumps thinking about that whipping me. Her top was an open blouse. It pushed her nipples high. Hip boots, white belt with a leather strap to them.

She looked gorgeous and dangerous. What she had in the basement left hundreds of scenarios she could play out. I knew whatever she had planned would be scary and erotic. She knew I had a high pain tolerance, so I was sure she would throw some of that into the mix.

Our first meeting was a test; her reaction to my call told me I had passed in flying colors. I have no idea what she would do to me tonight, but I was looking forward to whatever it was. The thought of her monster dick buried inside me made my ass twitch.

She took me by the hand and led me into the elevator; we went to the basement. It had changed when we got there; the horse was gone and in its place was an X, shaped device. Covered in black. There was a crossbar with a headrest in the center.

The device was supported in the center to a round metal pole. The frame was about a foot off the floor with a step to stand on. She instructed me to step up. Once I was spread-eagled to the sides, she buckled straps around my ankles and my thighs.

She touched a footpad, and it rotated my legs up and upper body down. She pressed another and adjusted the height so that she had a perfect angle to fuck my ass. She walked to my head. There was an open leather ring that fit around my face, and she strapped me.

She secured my arms at the wrist and upper arm on both sides. She went to a cabinet and removed a clear elastic ring device. She showed it to me and explained its purpose. I will place it around my balls and dick. It had a flap with a hollow cup to fit over my dick.

Once on, she snapped the cup over me; it let the head of my dick stick out to behind my flair. It had a raised ring; she attached another cup and slipped it over that, putting additional pressure at the flair and had a tube attached.

She left and returned with the bottle warmer; there was a large bottle setting in warm water, covered with a stretchy flesh tone piece of something. She pushed the hose through that film, and it slid in.

She told me, now your pre-cum will drain into that warm bottle until the session is over. I haven't decided yet if you will drink it or me. She positioned the cart, so it was directly below my dick. At this angle, my nipple chain and dick attachment hung free in space.

She moved the frame, so my body was just above horizontal. She stepped between my legs and put some warming oil on both sides; she poured a stream down my crack, I could feel my ass warm up. She said, how does that feel, my little girl? I said, great, thanks.

Next, she said, so my little girl, you were bad earlier/slap, hot points lit up on my ass as her knotted whip struck my left cheek. She said, you arrived late/slap, I jerked as my other cheek lit up. She continued, on purpose/slap, just for this/slap, do you like it/slap?

I said yes, do you want more/slap? I whimpered, yes, please. You don't sound very convincing/slap, you will have to do better than that/slap, or I will do this/slap, all night/slap. What do you have to say/slap about yourself/slap, little girl/slap?

She had made my eyes tear up, my ass was on fire, and the oil she had spread on my ass made the straps cling and hurt more. I said in a gasping female voice, just a few more, please. She struck me side to side for five minutes. She said, enough? I said yes.

She hit me two more times, once down the crack of my ass that made me scream. Then once swinging upward, clipping my balls which also wrenched a scream from my clenched mouth. She said I would keep this close in case you disappoint me, little girl. I said thank you.

She tilted my head back up to about a twenty-five-degree angle. She stepped close and forced the head of her erect dick past the opening. Only her head sat inside as my ass tried to adjust to the width. She said, how does that feel? I lied and said, wonderful.

She pulled out, waited a few seconds, and put the head back. She repeated this several times. Each time pulled a moan from my mouth. Then she pushed in two inches, set, withdrew the head, she repeated several times.

Two inches, three inches, four inches. She repeated. My dick began to leak pre-cum. After repeating four inches a half dozen times, she withdrew and stooped down. She said, dirty little girl, look at all that cum leaking out of you.

She said I would have to punish you/slap, until/slap, you/slap, stop/slap. She moved and asked, how much that was. I said I don't know you didn't tell me. Slap, slap, slap, slap, guess? I whimpered four inches, and she said, good girl, pressing four inches inside.

She withdrew completely, pushed in, and said, five, withdrew and pushed six, withdrew, pushed, seven. She paused; she started to fuck me, seven inches and back to the head. She spent a good twenty minutes fucking at seven inches. She said I am kind to you.

It was finally beginning to feel good, she had managed to loosen me up, and she was hitting my prostate just right. I could feel the cum leaking out of me. She plunged all seven in, and I had an orgasm. She felt me shudder, withdrew, knelt, and said, what have you done?

I told her I just couldn't help myself; you feel so wonderful. She said, good thing you know how to talk to me, Michelle; otherwise, I would have to punish you. Maybe I have fucked that out of you for now. She shoved seven inches inside. She said, eight, shove, nine, ten, Scream.

She had reached my inner door. Close enough to apply a little pressure but not enough to break the door down. She withdrew and shoved ten inches; again, I was sweating, moaning, gasping, and panting. She said, doesn't that feel fine? I couldn't speak.

She withdrew and shoved it back in again and said, I asked you a question? I still couldn't answer, so she shoved and entered the door by two inches. I screamed; it feels wonderful. She pulled back just enough to leave my inner sphincter.

She fucked me another twenty minutes or so, opening the door, closing the door. Eventually, the pain subsided to below screaming level and I was moaning. She said, you love that, don't you, nasty little girl. I replied that I loved it.

If I could just become accustomed to this depth without the crazy cramping and pain, it would be wonderful. She was massaging my inner sphincter to the point that it was no longer a tightly clinched opening, but like my anus, I would be in heaven.

She had been fucking me for almost three hours and still had four inches left to push in, and she didn't seem ready to cum. I couldn't believe my ultra-tight ass wasn't affecting her. She had super stamina like her cock.

Like on cue, she said, up until now, I have been doing the prep work. Now I will fill your oven and make you a milkshake to remember; I hope you brought your appetite because it will be a full meal, ready?

I said, yes, Bobby, fuck me and fill me with your milk. She had been resting just outside the inner entrance. She pushed, and I felt a wave of pain as she pushed the entire fourteen inches inside my ass. It was pain, pleasure, spasms, the feeling of being split open.

I whimpered, cried, moaned, gasped, panted, sweat, and cum at the same time; she had fucked another orgasm out of me. I was squirting, and my ass was pushing, squeezing, fighting to adjust to the size. She withdrew to ten and pushed over and over; she fucked me.

She pulled back all the way then plunged back in all the way, her heavy balls striking mine with enough force to hurt. It added another pain to the overwhelming pain I was experiencing. She fucked me until I began to calm down and quit shaking.

She established a rhythm and didn't change gears for a really long time. Finally, my ass had adapted to her size. She knew, and she fucked me harder, trying to get more in me, although she was bottomed out. I started to whisper, fuck me, fuck me. She did.

I could feel her swell, yet she still raced in and out of my ass. She slammed into me, and I felt her unleash her fire hose. She squirted then again, withdrew, plunged, and shot again. I could feel her trying to ejaculate even more than she was spent.

She pulled the bottle warmer between my legs and took the attachment for my ass out of a drawer while still pressed to me like we had one skin. She slid out, holding it under me. She withdrew and pushed it to me. Taking the hose, she slid it into a waiting bottle.

She opened the valve and filled four bottles to the top before I stopped leaking cum. When I was drained, she caped the bottles, brought the mask around, placed it over my face, and said, lick this clean as she held the hose up into the air.

She kept it there until every running drop of her cum had reached my mouth and was licked up. In addition to constantly leaking cum, when she cummed, so did I; I had experienced three orgasms while she fucked me and had leaked non-stop during the entire fuck.

She said, Michelle, I have never cummed so hard or so much in my entire life. Your ass is wonderful, and so are you. I hope you enjoyed this lesson as much as I did. I nearly fainted. I look forward to repeating this in about an hour or so. I need time to recover.

I told her it had its moments, that's for sure, and I will keep trying until it is a pure pleasure from the moment you start until the moment you stop. I dream of that day, and I know that only practice will make that possible.

Until that moment, I am yours to train. Thank you, Bobby, for your patients and care. She adjusted me to standing, removed the restraints, helped me down, and we went to the couch and rested. My head next to the intruder that had so thoroughly tamed my ass.

We played on the couch for over an hour. I said we should smoke a bowl. She agreed, and we both felt better. She said, Michelle, I have to tell you that was the strongest orgasm I have ever had. I told her, I am so happy you find me everything you hoped for.

Laying close to her penis, I decided to see if I could wake that sleeping monster up. I sucked, nippled, licked, and did everything I could think of to breathe life back into it. I worked at getting a rise out of her, and after a while, it began to respond.

I didn't stop until she was fully erect. I said, this time, Bobby, I will do the work; you lay there and allow me to please you. I got up, went to where she had fucked me earlier, and brought back the bottle warmer and lube. I said we are going to need these.

The warmer still had several empty bottles along with the full ones. I poured some lube in my hands and massaged her dick. Reaching behind, I lubed my ass. I put my knees on either side of her legs. I bent and kissed her. I kissed her neck and breasts.

I sucked on her nipples, rolling each in my mouth. She was making soft moans. I worked my way down her chest, licking and kissing as I went. I kissed my way to the base of her cock. Setting up, I centered myself over her erect dick.

Allowing it just to touch my anus. I told her, this time, I am going to enjoy this as much as you. With that, I shoved six inches of her inside my hungry ass. I slid back and forth for a dozen strokes or so. The feeling was exceptional, and my dick was hard and throbbing.

I pulled back to the head, and in one move, buried to the balls deep inside me; there was only a moment of pain, and my ass sucked her inside like it wanted more. I withdrew and plunged, my dick leaking as I rode her entire length for the first time and loved it.

The fucking she had given me earlier had done the trick; my ass couldn't get enough of her. Every stroke made me drip cum; every time she passed the second opening, my body quivered and spasmed. I drove her in, over and over. It didn't matter how long.

All I knew was I wanted to ride her all night. I loved it, my ass loved it, and my dick loved it. Along the way, I shot a streamer of cum that landed on her breasts. As it happened, I drove her deep inside me, squeezing her as my dick jerked and shot long strings of cum.

It was powerful, it was incredible, and I didn't want it to stop. I was racked with pleasure. When I was finally drained, I resumed riding up and down. I was an endless rocking body. I lost track of time, and I don't know how long it continued.

The only thing on my mind was the feeling of her dick filling my ass. I continued long enough for my dick to begin to rise again. I felt her buck inside me, and she erupted. I held her dick pressed inside me as deep as it would go.

My ass was convulsing around her, and it continued until she was empty. She was an endless stream of hot cum, I felt her shoot three times, and each felt like she pumped quarts inside me. It was glorious. We were both spent and unable to move.