My New Life with Her

(This is a continuation of "My First Session with Her" and incorporates Staci from "Domination Road Trip." I have attempted to make this story stand alone, but it may make more sense if you read the other two stories first to get a background on the characters.)

My owner, Ms. Andrea, was finally satisfied with the blow job I'd given her strapon, and released her grip on my hair, and pulled her cock out of my mouth. Ms. Gilbert grabbed my hips and slammed me a few more times with her strapon, before she pulled out of my ass and laughed. I collapsed, bent over the table, and briefly thought of how my life had changed in such a short time.

Just a few short weeks ago, I was a man, looking for a session with a dominatrix. Now, I am the personal secretary, and sex slave, of Ms. Andrea. My new hair, new tits (36DD!), improved face and ass, piercings, tattoo, and wardrobe were all done to her specifications, and for her full use and pleasure. Ms. Gilbert owns a company that Ms. Andrea was trying to do business with, and it was my job to convince her to complete the deal, which meant paying with my ass, and letting them double team me she attempted to close the deal. I only hope that I have done my job, and that my Mistress is pleased with me.

"Well, since we're now partners," Ms. Gilbert started. I looked back over my shoulder at her. "Not you, stupid slut, I meant Ms. Andrea," she laughed as she swatted my ass and said, "Get back to work! Type up these contracts we just signed." I stood up and grabbed my thong string and swung my hips to work it back up my ass. My skirt was super short, but I did my best to pull it down, so that it at least covered part of my ass. I wobbled over to my desk topless, the nipple clamps still attached and biting into my big bouncing tits. "She's going to be walking funny for a few days after that, but she better get used to it," Ms. Gilbert stated. "Anyway, before our slut interrupted us, I was saying that since we are now partners, I have a big meeting out of town in a few days with a client, and I was thinking I could definitely use the services of little Ashleigh there. What do you say?"

"I don't know if she's well-trained enough yet," Ms. Andrea said. "I would hate for her to embarrass us."

"She'll be fine. We leave tomorrow morning for Europe, so I'll take her with me right now. She will spend the night at my house and we'll be up bright and early for the flight," Ms. Gilbert said. "You better go pack, slut," she told me. I stood up and followed the women down the hall to my room. Apparently my new business suits had been delivered sometime while I was getting pounded, because when I opened my closet, they were in there. Ms. Gilbert picked out the baby blue one, and the pink one, and handed them to me. We also packed my little black dress, a formal dress, a few "casual outfits," (which were short skirts and low cut tops), and of course a full compliment of lingerie, heels and sex toys.
Just as we were ready to leave, Ms. Gilbert said, "Oh my, what do we have here?" I turned around, and saw her smiling and holding my French Maid outfit. "I think we're staying in tonight," she said, and handed me the outfit.

I took off my skirt, but kept the thong and heels, and put on my black thigh high fishnets, a black push up bra, and the costume, of course, with the little hat and duster as the finishing touches! "You look really sexy, I'm going to love this!" she exclaimed. "Meet me at the car in two minutes," she said.

I grabbed the handle of my suitcase and wheeled it out to the car as best I could in the heels and everything, boobs bouncing the whole way and on full display in the low cut costume. She rolled down the window, and I bent at the waist and leaned in to see what she needed, which gave her full view of my tits. She smiled and told me to put my suitcase in the trunk and then get in the backseat, which I did.

We pulled up to her house a short time later, and I took my bag inside. "Go grill me some chicken," she demanded. I got some chicken and walked out onto the balcony and put it on the grill. I stood out there with the spatula and tended to her meal. She called me in, "Bitch get in here and rub my feet while I'm waiting!" I scurried back in and got on the floor and started rubbing.

I made the mistake of bringing the spatula in with me! She grabbed it from me and leaned over and while I was rubbing her feet, I felt a "WHACK!!" on my ass! Holy shit! "Keep rubbing my feet bitch, while I spank you," she laughed. The metal spatula didn't take long to heat up my ass and leave it red, and she continued to hit me with it.

By that point I was crying a bit because my ass really fucking hurt. She handed me back the spatula and told me to get back out there so that her food didn't burn. I stood up and could feel my skirt fall back down over my burning red ass and I strode back out to the grill, making sure to really roll my hips and move my ass as I did.

I finished up and brought her chicken (and a potato) back inside and set the table for two getting us each a glass of wine. My plate was of course empty, and she told me I could fix myself a salad so I did that. I came back out and she set my plate on the floor and told me I could eat at her side, on the floor, with no fork. I did the best I could and finally finished while she was still eating, since my salad was so small and she was still enjoying the wine. She pulled my head between her thighs and told me to get to work. I got her off pretty quickly and she demanded I do it again, so I did.

She told me that was all for now, and told me to clean up, so I did the dishes and cleaned off the grill. When I came back inside, she was lounging on my couch, watching TV, naked except for a strapon!

She just pointed down at it, and said "I'm not doing any work tonight, at all. If you want some lube, you better provide it with your whore mouth." I got down and started stroking it, knowing that part of it was in her, getting her going as well. I looked up at her and winked and buried her strapon into my mouth, bobbing and drooling and getting it wet. Then I pulled it out and stroked it, and repeated...I'd done this enough times by now to know what would probably turn her on.

Then I stood up and grabbed her strapon, and buried it up my ass in one quick motion, and slid all the way down to her lap. I reached back and put my hands on her thighs and arched my back and fucked her good and hard till I heard her cum, then I stood up and bent over and she spread her legs and grabbed my hips and grabbed me until I fell back into her lap with her cock all the way up my ass! She pushed my head down so that she could watch TV and held my hips while I worked her cock in my ass until I felt her cum again

I rested there for a few seconds until she slapped my already red ass and told me to get moving. I pulled my feet up onto the couch on either side of her legs so they were splayed out wide near my feet but our thighs were resting on each other. Then all I had to do was lean back and forth to get the fucking motion going. She did grab my hips to help the balance, but the rest was all me! Not too long and my tits were shaken out of my top and started bouncing up and down as I fucked her cock harder and faster.

Once she was done, she pushed me onto the floor and told me to put the metal jeweled plug back in, that she was done with my ass for now, and to bring out some rope. My tits were still out, from the hard fucking, and I just left them out...I was a sweaty drooling mess by this point, my hair was disheveled, my makeup was smeared, and I was staggering around, and she laughed and told me to get moving. She also told me to take the bra off, so I did that, even though at that point it was just providing support.

I came back with the plug in, as told and the rope and she told me to lie down on the floor. I did as I was told, and quickly found myself hogtied, licking her toes as she watched TV and drank wine.

She let me do that for awhile, then she picked me up and tossed me on the bed still hogtied, then she lay on her back and had me suck her strapon for awhile, until the stimulation made her cum again. The bobbing of my head was causing my nipples to rub against the satin sheets and I started to get worked up myself, but I dared not cum without permission.

Eventually she was done with me, and re tied my hands in front of me (just to each other) and left my feet tied to each other. I thought I was going to get to drift off, but she attached the nipple clamps! She curled up behind me to spoon me, so I felt the strapon at my ass, but it was blocked by the plug. Once the pain in my nipples subsided a bit I drifted off to sleep....with her strapon against my ass, the plug in my ass....her arms around my waist, boobs out and nipples clamped, my platform heels, thigh highs, thong and maid outfit still on, and me a drooling, exhausted, disheveled, used mess of a French maid.

I woke up suddenly the next morning to a pulling on my nipple clamps and a full feeling in my ass! When I went to yell, the plug that had been in my ass all night was shoved in my mouth (good thing I keep my ass clean) and Ms. Gilbert was fucking my ass with renewed force! Apparently the night off and sleep had done her well. Also, her strapon was bigger than the plug, so even though my ass was open, it wasn't open THAT much! She reached around me and tugged on the clamps and grabbed my hips to rock me back and forth and cause my tits to bounce and thus make the clamps tug more on my nipples.

When she finished, and pulled out of my ass, she told me to make her some breakfast on the grill...as I was! I staggered out of the room, walking funny of course and having trouble because my legs were so tired and those heels are tough to walk in on a good day, let alone my current state. The good thing was that my ass was empty for the first time in hours, which was good because it needed a chance to recover. I could still feel it was open and the breeze on my still red ass as I walked out onto the patio to grill some breakfast for her. The morning breeze also hit my nipples, making them hard, even though the clamps had already done that! The walk also made my unsupported tits bounce, with the clamps tugging my already sore nipples even more!

When I came in, she had a two sided penis gag, and locked it on me. Part went in my mouth, so I had practice sucking, but part stuck out. She sat down at the table and put me between her legs, so I could fuck her with the penis end while she was eating breakfast.

After she orgasmed a few times and finished her breakfast, she told me that we needed to be on our way. We both showered, separately of course, and Ms. Gilbert came out in a moderate length khaki skirt, fitted polo shirt and sandals. I had on a short red and black pleated skirt and white tank top with cork platform sandals. There was a lacy white thong laying out for me, so I had that on as well, but there was no bra, and I knew better than to ask for one! Ms. Gilbert reached down my top and tweaked my nipples so they were hard and showed through the thin tank top. Instead of being embarrassed, I looked down and thought about how good they looked, as I grabbed both of our suitcases and headed out to the car.

We got to the airport without incident. While she was driving, Ms. Gilbert had reached over and pulled my tank top down so that everyone driving by could see my tits, but at this point, I was pretty used to that, so it hardly seems worth mentioning. I got out of the car, and Ms. Gilbert was right behind me! She pushed me down over the hood, smashing my bare tits into the metal. I felt my skirt flipped up and my thong quickly moved to the side. Before I could even look back, I felt a large rubber plug invade my ass. I could tell it was pretty long, but more than that, it was VERY wide. Ms. Gilbert drove it all the way in, put my thong string back, and patted my ass. "That should get you ready for the flight, and make the walk there more interesting," she laughed.

As I straightened up, and moved my hips back and forth, I realized that there was no way I was going to get comfortable with this plug. It felt like someone's fist was in my ass (which Ms. Andrea had done before), and made walking in the heels and dragging the suitcases a lot more difficult. Ms. Gilbert walked ahead of me, and would occasionally look back to laugh and yell at me to walk faster. She had allowed me to pull my top back up, but without a bra, I was getting a lot of looks, because I could feel how much they were bouncing, so I can only imagine how hot it looked to others.

We got to the ticket counter and thank goodness Ms. Gilbert decided to check our bags. I'm sure it was only because she did not want to deal with the possible hassle that the sex toys would cause us as carry on items, because if she thought we could get them on board, and humiliate me in the process, she probably would have done it. The security agents gave me a few quizzical looks as my carry on and purse went though, but they let us through and we got on our plane.

As I reached my seat, I realized that stowing my carry on in the overhead bin would be a problem. I didn't really have a choice though, and as I bent down to get it, I felt my skirt ride up, and knew my ass was exposed. I quickly straightened up and reached up with my bag, again exposing my ass. Sitting down was also VERY difficult, and Ms. Gilbert laughed as she saw me squirming in my seat, trying to get comfortable. She sat down next to me and smiled. The first several hours of the flight were uneventful. We both got out our laptops and did work. I worked on typing the contracts and Ms. Gilbert worked on her presentation.

I asked Ms. Gilbert if I could go to the bathroom, and she said that I could. She also mentioned that I could take the plug out if I so desired! I scurried back to the restroom as fast as I could and pushed the monster invader out of my poor stretched butthole. After a few minutes, I washed my hands and got ready to go back to my seat. Then I realized that I had no where to hide something that big! My skirt and tank top were way too small, and didn't exactly have pockets! Did I want to carry a large pink butt plug back through the cabin in front of everyone, or did I want to carry it in my ass? Then I had an idea! I opened my mouth and started to feed it back toward my throat. Just as the tip was brushing my tonsils, I closed my lips around the base. I put my head down, and put my hand up near my mouth and hurried back to Ms. Gilbert, making sure to breathe through my nose.

She saw me sit down easily, and didn't see the plug in my hand and asked, "Where it is, Ashleigh?" I looked at her, and pushed the plug out into my hand. "Clever girl, now suck it" Ms. Gilbert commanded. My face flushed red, and I worked the plug in and out of my mouth, pretending it was one of Mistress's cocks. "That will do," she told me, and I immediately stowed it in the seatback in front of me. It was getting dark, and the attendant brought us our dinners and pillows and blankets, as it was an overnight flight. Ms. Gilbert reached into my purse and handed me a white satin and lace baby doll, which apparently was my sleepwear. I gave her a questioning look, and she slapped me and told me to get under the blanket and get changed!

The tiny skirt was off in no time. A quick zip and a shift of my hips, and it hit the floor. The tank top was a bit tougher to do while holding the blanket, but I managed. I was naked under the blanket, except for the thong, and wondered how that tiny piece of material was going to fit. I knew it wouldn't fit past my tits if I tried to go over my head, so I put my legs into it and worked it up my body as best I could. Ms. Gilbert hit me because I was thrashing around so much, but I finally got it up over my hips, worked the thin straps up my arms, and settled my tits into the satin underwire cups.

I got down on the floor (on my knees) to pick up my skirt and tank top, but when I raised my head, I bumped into something hard and rubber. Ms. Gilbert had changed into a satin pants/button up shirt pajama set. The fly was unbuttoned, and a strapon stood erect. She gently guided my mouth to it, and I began to suck her, as I had done many times before. The attendant came by and asked Ms. Gilbert if she wanted a drink, and if her seat mate would want one when she got back. Ms. Gilbert looked down at me, under the blanket and said, "We'll both take water, thank you."

Then she got up on her knees, and pushed me to lean back so that I was almost touching my ankles. She pulled down the straps, baring my tits and thrust forward so that her cock was between them. She was titty fucking me! I braced myself with one hand and pushed my tits together with the other, so that she could really build up friction. She still got the tip to my mouth a few times, which I was really trying for, since all the spit I'd put on it was now between my breasts, and I didn't want her cock going in my ass dry.

After a few minutes, she really began to fuck me, and I heard her breath getting faster, and knew she was about to cum from the friction, which she did. She sat back down, which gave me a chance to pop her cock back in my mouth and get it wet, thank goodness! No sooner had I done that, than she recovered a little bit, and pulled me up on her lap, so that we were both under the blanket, except for our heads, and both facing forward. I felt the cock resting between my cheeks and knew it was only a matter of time before I joined the "Mile High Club." I had thought about this, in my former (male) life, but never in this way! "I'm going to fuck your ass in public now, slave," Ms. Gilbert growled into my ear.

With that, she pushed me forward a bit, and commanded me to spread my cheeks as she lined up her cock with one hand and grabbed my shoulder and pulled me back with the other hand, spearing me on her cock. It was a pretty good size, and my ass had had a chance to recover from the plug, so I bit my lip and wiggled my hips to try and get it in there the best I could. The attendant came back around with our water, and I reached out with my bare arm to take both of them. I'm sure it looked weird, that I was sitting on her lap, but I was more focused on not giving it away with my facial expressions, which was hard to do with something that big in my ass!

I flexed my hips and ground my ass on her cock as best I could in the limited space and worked her to two more orgasms. She fondled my tits and pinched my nipples as I worked her, and I really wanted to cum myself, but knew better than to do so, as she never gave me permission. I also did not want to have to clean up my mess in front of everyone, so I somehow held off. When she was done, she lifted me up off her lap and put me back in my seat, and we drifted off to sleep.
We awoke the next morning when the attendant nudged us to tell us the plane had landed. I didn't have time to change, and was forced to walk off the plane in the baby doll. It was not inappropriate, as I was covered; it was just really tight and really low cut. I know people were looking, but it was because I looked good. The bags were waiting for us, and we took a cab to the hotel. Our meeting was in a few hours, so we showered and got ready.

A black lace push up bra and "BITCH" thong were on the bed, as well as a short, low cut, white blouse. I hurried and put all of them on, and looked over and saw my pink business suit on the hangar. I tugged the tight skirt up and zipped it, and noticed that it barely covered my ass. The coat buttoned up to right below my boobs, which held them up and created a ton of cleavage. I put my hair up in a bun and put on my secretary glasses and dangling hoop earrings. I did a spin in front of the mirror to make sure I looked good, and then we left for the meeting.