My First Session With Her

Let me start out by describing who I was. I am 24 years old, 5'6" about 150 pounds, fair skin and short hair. I'd been cross-dressing for about seven years, and had quite a collection. I was living with a roommate, Jane, who had no idea about my hobby. In fact, I'm pretty sure she'd have been freaked out if she found out, so I'd kept it secret. I consider myself to be straight, but my roommate and I were just friends.

For a few years now, I've wanted a woman to dress me up as a girl and dominate me. Sometimes, I'd look on various websites, and get very close to actually going through with it, only to have something happen at the end. Something always happened though: I found out it's a bogus offer, the woman is totally unattractive, or I decided not to go through with it. (I always let them know beforehand, as it's rude to stand people up.)

My roommate was gone for the weekend, and the weather was getting warmer, so I decided to try something a little daring. I glued my DD breasts to my chest, and then bent down to slide some white stay up thigh highs up my legs, feeling my new tits pull me forward as I did so. Next, I strapped on my black seven inch platform stripper heels, and stood up and walked over to my dresser, where I hid my bras and thongs. My white thong that ties at the sides and has the word "SLUT" in rhinestones in the back was calling my name, so I grabbed it and put it on, moaning as the soft material found its way between my ass cheeks. I put on a white lace push up bra, and sauntered over to my closet and took out my school girl outfit. The white blouse tied right below my boobs and showed a ton of cleavage, and the short red and black pleated skirt barely covered my ass. I gave the strings of my thong a tug so that they showed above the waistband of the skirt, and then I grabbed my favorite dildo and strode out to the front porch!

It was super dark outside, so I figured this would be a good chance to do something a little daring, and then hopefully work my way up to actually going through with my plans to let a real woman dominate me. The first few minutes, I just walked back and forth on the porch, and got used to the thrill of being outside dressed up, and enjoyed the feeling of walking in the heels. Then I got a little braver, and started sucking the dildo, right there on the porch. Once it was wet, I went over to the porch railing and bent over it. I flipped up my tiny skirt, and moved my thong to the side. A few swats to my backside really increased the mood for me, and before I knew it, I had shoved the dildo all the way up my ass!

I used one hand to work the dildo, while the other hand played with my tits. I started rocking back and forth, and then I stood up and turned around and started ramming my ass against the porch railing, which drove the dildo in and out for me, and left both my hands to spread my ass or play with my tits, which I alternated doing. At that point, I was so worked up; I stood back up, and climbed up on the porch railing. It was cement, and kind of wide, so I knew this would work. I balanced on the heels, squatted down and used my ass muscles to push the dildo most of the way out. Then I squatted ALL THE WAY down, driving the dildo all the way back into my ass, and then pulled myself up a bit, and started fucking myself that way really fast to get my tits bouncing.

After awhile I was so worked up, I came in my thong, stepped down, and pulled the dildo out of my ass. The night was still young though, and I wanted to enjoy the weather a bit, so I adjusted my skirt, and sat up on the porch railing and crossed my legs like a girl. I looked around a bit, and out of the corner of my eye, I saw our big black neighbor sitting on his porch! Now, he is old and hard of hearing and vision, but it gave me such a scare, I jumped up and ran into the house and shut the door! I have no idea if he saw me or not, but I was super scared and quite a bit turned on.

At that point, I battled it out in my head and decided that if I could do that, then I was ready for a real life experience. Since I was already in the mood, and dressed the part, I wasted no time in logging onto my computer and starting my search. After some searching, I found a woman in my area that seemed to fit the bill. She was a little older than me, attractive, and interested in the same fetishes. We sent a few e mails back and forth, and then she called me. Once everything was in order, she told me to meet her at her house tomorrow, wearing exactly what I was wearing right now, except to add a pink jeweled metal anal plug.

I set to work getting my outfit cleaned for the big day. I took off my breasts, and washed all the outfit pieces. The adult store wasn't far from our house, so I went and bought the required anal plug, much to my embarrassment, as I had previously just bought everything over the internet. After finishing up the laundry and making sure everything was ready for the big day, I went to sleep, although I didn't sleep very well, as I was so excited.

I woke up and put on everything as instructed. She told me to wear my tits, but not glue them on, so I did as she said. A quick check in the mirror revealed that everything was in place, except the anal plug. I bent over, spread my ass cheeks and pushed the smooth plug into my ass. It was a bit cold, and kind of big, but I managed to get it all the way in, sliding my thong string back into my ass to hold the plug in place. A sweatshirt and sweatpants over top the outfit, and I shuffled out to the car and drove over to her house.

When I got there, I was astounded by how big and nice the house was. She told me her father was very rich and had a condition that required a caretaker. So, he had built her a private wing of the house, which she designed, in exchange for her living there and caring for him. I pulled into her driveway, as directed, and took off the sweatshirt and sweatpants before she could see me. Nervously, I stepped out of the car, and walked up to the door, my hips swaying from the super high heels and the plug in my ass.

I was met at the door by Ms. Andrea. She was even better looking in person, and I instinctively knelt down in the doorway. Before I looked down, I took in that she was about 30, as she said, with beautiful brunette hair, and perfect C cup sized breasts, and clearly in great shape from frequent workouts.

"My my, aren't you a cute little sissy?" she remarked as she collared and leashed me.

"Thank you, Ms. Andrea," I replied.

"Do a little spin for me, and bend over, I want to see that ass," she commanded. I did as I was told, spinning around, and then stopping to bend at the waist. She pulled up my skirt and upon seeing the jeweled plug firmly in place said, "Very good, slut, you have followed my first command. However, you won't need these," she said, as she pulled my hands behind my back and cuffed them together. "Oh I like that," she laughed, as she noticed that with my hands cuffed behind me, I was forced to thrust my breasts out. She then blindfolded me, told me to stand, and led me down some stairs.

It felt colder and darker, but I knew better than to ask any questions. I felt my breasts being lifted away from my chest, a cool liquid applied and then her hands pressed my breasts firmly against my chest. She then spend a few minutes near my ankles and I heard a few "clicks." Then I felt the cool liquid on my head, followed by what had to be a wig.

She removed my blindfold and I saw myself in the mirror. I had long blonde hair, and my shoes had been locked onto my feet! I looked around and saw a fully equipped dungeon and Ms. Andrea in the corner walking toward me in full leather attire. Her brunette hair was pulled back in a ponytail, and she was wearing a black leather corset that supported, but did not cover her beautiful breasts. She was wearing tight black leather pants and black platform heels. She was carrying a paddle in one hand, and as she got closer, I could tell she had a strapon belted around her waist!

"Do you like my dungeon, slave?" she teased, as she stroked her cock. "Daddy doesn't know about it," she giggled. "I designed it, and had it built without his knowledge. I've been training slaves down her for almost ten years, and he's none the wiser."

"As for you, slave, you told me you've backed out before, so I've taken some measures to ensure that you don't do that to me. First of all, your shoes are locked to your feet. Only I know where the key is, so you will have to please me in order to ever have them taken off. Also, both your breasts and wig are glued on with special glue that will keep them on for a minimum of two days, and after that, can be removed with a special solvent that I have. So, not only will you need to please me, it looks like your weekend just got a little bit longer. Tomorrow morning we will call your boss and let him know you are unable to make it to work. You better please me, or you'll have to make the call with my cock up your ass!"

Needless to say, I was simultaneously scared and aroused. Ms. Andrea pointed, and I obediently got down on my knees, which was difficult in the heels and with my hands still cuffed behind me. She circled me a few times, and then stopped behind me. She pushed my head to the ground and told me to hold my hands up in the air behind me, which gave her total access to my ass. Next, she lifted my skirt off of my ass, and flipped it up onto my back, and I started to shake in anticipation of what was coming next.

All of a sudden, I felt a breeze and then a WHACK on my ass! I screamed and lurched forward, but she laughed and I got another WHACK! I started to tear up a bit, and I must have moved a little, because she took one hand and grabbed the chain to my handcuffs and yanked my hands up further as she continued to paddle my poor ass. I started to cry and begged her to stop, but she kept going. My ass felt like it was on fire, and yet still she persisted. "Would you like me to stop, slave," she teased.

"Yes, Ms. Andrea, please stop," I sobbed.

"Not yet," she stated. She let go of my cuffs again and started hitting me even harder. I was sure I couldn't take much more. I started to collapse onto the floor. I felt totally broken. She asked me again, "Do you want me to stop, slave?"

"Only if it pleases you, Ms. Andrea," I managed to cry.

"Very good, slave, you are a pretty quick learner," she said. "That is the answer I was looking for," she said, as she put down the paddle and began to rub my poor inflamed ass. "It didn't take very long to break you, did it? No, I think we're going to have a lot of fun this weekend," she laughed. She held up a mirror for me to see what she had done to my ass. Her paddle was engraved with the word "SLUT," so that had been imprinted on my backside. She tugged at my leash and I obediently crawled after her, even though it was really hard just shuffling on my knees. "Up," she said.

I climbed up onto a padded sawhorse, and Ms. Andrea cuffed my legs to two of the legs. Then, she un-cuffed my hands, and cuffed them to the remaining legs, so that I was propped up on all fours, with easy access to both my mouth and ass, my upper body hanging off the end, so my tits were tugging at my chest. She stepped in front of me, her strapon cock right at eye level. She removed my blouse, and I lunged forward for her cock, and she pulled it away and laughed. "Such an eager little cock slut," she laughed. To prove her control, she stepped away and did a few more laps around me.

Then she stepped up again. For some reason, this time, I kept my mouth closed. I immediately knew this was a mistake, and expected a terrible punishment, but instead, Ms. Andrea simply laughed, and pinched my nose closed with two of her delicate fingers. After about thirty seconds, I was forced to open my mouth, and she laughed again and sunk her cock all the way down my throat! I started to gag and drool, and she grabbed me by my hair and held me there until I gagged and thought I'd puke, then she let me go, before cramming her cock all the way back in. "You are not smarter than me, slave, do you understand? Do not try to pull that with me again, I own you, and you do what I want when I want," she said calmly but firmly.

"Now let's see about that pretty little ass of yours," she cooed, as she pulled out of my mouth and stepped behind me. I felt her lightly scratch my back with her nails as she paced around me. "My cock is a bit bigger than your plug, so you're going to feel something, but trust me, you'll be glad you had that in there to get you warmed up." I felt her hands at my ass, as she flipped my tiny skirt up onto my back. She slowly slid the plug out. Right as it left my ass, the tip of her cock replaced it! I screamed and thrashed in my bonds, and tried to get away, but to no avail. Ms. Andrea spread my ass cheeks with her hands, and fed her cock slowly into my asshole.

"I do enjoy taking a girl's anal virginity," she said. "It's another notch on my bedpost. Another little boy conquered. I will add you to the others. Oh, look! I'm all the way in!" she exclaimed, as I felt her hips touch my ass. "That was pretty easy," she laughed. "You must have been practicing on yourself in your room for a long time. That's pretty pathetic. At least now you are getting what you need and deserve, you naughty little sissy," she said as she started to saw in and out of me faster and faster. I continued to try and get away, and dislodge her cock from my ass, but was unsuccessful.

As she slammed me, she reached forward and mauled my tits with her hands. I squealed as the fucking shook my tits loose of the bra and tugged on my chest, as I'd always imagined they would. She took her forearm and dug it into the back of my neck, forcing herself in and out of me at top speed, burying the cock all the way in and taking it almost all the way out, over and over again. I started to scream and moan, I couldn't take it anymore!!

"Scream as loud as you want, you little bitch, no one can hear you down here," Ms. Andrea laughed. "In fact, no one even knows there's anything down here. I can keep you down here as long as I like and do whatever I want to do," she said.

"Please, Ms. Andrea, may I please cum?" I begged.

"No, you may not," she said. I thought I couldn't take any more, but then she pulled out a bit and made a twisting motion as she shoved it back in. She started twisting her hips as she drove in and out. I swore I was going to lose it!

"Please Ms. Andrea may I PLEASE cum, please Ms. Andrea?" I pleaded.

She pulled out of my ass and positioned her cock directly under mine. "You may cum now, slave," she directed me. I came harder than I'd ever cum in my life, and it was directly onto her strapon. I'd see enough female domination movies and read enough stories to know what was probably coming next. That did not mean I was ready for it, or that I wanted it. The strapon was right at my mouth again, and I clamped my lips shut and refused to open them.

Ms. Andrea just kept walking forward, until the cum-covered cock touched my face. I recoiled in disgust and moved my head, which just succeeded in smearing my face with cum. She moved, and I moved again, which smeared cum all over my other cheek. "Well slave, you have a choice," she stated. "Your face is now full of your own cum. The only way that is coming off is by your own tongue. We are going somewhere in a little bit. You can either go with your cum on your face, or lick it off, like a good little bitch, what will it be?"

"I will lick my own cum, Ms. Andrea," I said, as I opened my mouth as a sign of my submission. She used the strapon to scoop the cum from my face into my mouth. I swallowed the entire load, and licked my lips to make sure I got it all. My face started to feel a bit crusty and I moved my jaws and Ms. Andrea laughed.

"It's impossible to get all of it. I guess you should have just sucked it off my cock in the first place, huh, sissy? That's an important lesson for you," she laughed, as she undid my bindings. "Stand up, and strip," she commanded. I stripped down to my bra and thong, and waited for her next instruction. Ms. Andrea went to the corner and came back with a short white outfit on a hanger. She handed it to me, and I realized it was a nurse's outfit! I put it on, and buttoned it up as far as I could, but it was obviously made for someone with smaller tits; my DDs barely fit, and showed tremendous cleavage. To make matters worse, the hem barely covered my still red ass, and as I walked around the dungeon, I swore anyone looking could see the "SLUT" still paddled onto my ass cheeks.

"It's time for daddy's medication," Ms. Andrea informed me. "You are convincing enough for his level of vision, and I expect you to give him a little show," she continued. "Pretend to drop something, and bend over to pick it up. Learn over him while he's taking his pills, you know, things like that," she offered, as she put a sweatshirt and sweatpants on over her domme attire. Then, she turned and started up the stairs, and I stayed at the bottom of the stairs. "You better get up here FAST slave," she barked, and I hesitantly followed her up the steps.

By the time we got to the main wing of the house, my feet were killing me! I was not used to doing so much walking in my heels. I usually just took a few steps around my room, posed and then flopped down on my bed and stuck something in my ass. All the walking really wore out my legs and feet! We got to an office where an older, dignified looking gentleman was listening to some music. "Hi daddy," she smiled sweetly to the old man. She giggled and gave him a kiss on the cheek. "I thought you might enjoy a little treat today," she said, as she motioned to me. "Ashleigh will give you your medicine and take your temperature," she told him, as I shuffled over to him, face as red as the cross on my uniform! I hesitated, and she gave me a discreet, but convincing swat on the ass!

I dropped the pen that was in my hand, and bent over at the waist to get it. "Well, young lady, it looks like nurse's outfits are a bit shorter than they were in my day," he laughed as I brushed my ass against his hand.

"Oops, my mistake," I said in my highest voice. I handed him his medication and a glass of water, which he took without incident. Then I reached into my bra and grabbed the thermometer. I leaned over him, so my tits were in his face, and stuck the thermometer in his mouth. Once it registered, I said, "Looks normal," and shook it back and forth, causing my tits to jiggle. My face was so red; I felt that maybe someone should take my temperature. I wanted to crawl into a corner and cry.

"Ok, we'll be off now, daddy, see you later," Ms. Andrea giggled as we left the room. Once we were out of the room, she turned to me and said, "You are such a natural girl, my little slave! Your face was so red the whole time, though. I could tell you were so humiliated! I am so impressed, though. I think I will reward you!" We had walked all the way back over to her part of the property, and I saw a large pool. "We're going swimming," she informed me, as she led me into the changing room. She handed me the key to my shoes, and told me to get completely naked and get in the shower. I looked at my tits, and Ms. Andrea assured me that both my tits and my hair would be fine.

I did as I was told, and she handed me a bottle and told me to lather up. I noticed it burned a bit, and as the water washed the soap off of me, I noticed I was totally hairless from the neck down! Ms. Andrea saw me and said, "There, that's much better! I can't have my girl all full of nasty hair now, can I? You need to look good in a bikini," she said, as she handed me what appeared to be a ball of pink string. I untwisted it, and found that it was a tiny thong string bikini. I wasted no time tying the strings at the side, and sliding the thong into place. I had to shift my hips a bit to make sure the material was properly up my ass, and that my cock was tucked back and out of the way. Next, I tied the top two strings of the top around my neck, while Ms. Andrea tied the remaining two behind my back. She put on a similar a blue bikini that looked stunning with her dark hair and tanned skin.