Picking The Wrong Mistress

How my story begins. I always fantasized about being a slave to a mistress, either bound or feminized.

I always searched the internet looking for a mistress that could help me explore some kinky things and help me make some of my fantasies come true. Living in Central Jersey and being married with 2 kids I didn't get to play much. My wife is very conservative, especially when it comes to sex. A blow job is a stretch with her and bondage, dress-up or using toys is rare. For some reason she doesn't seem to really enjoy sex, me I'm always looking for action.

But I digress; I started corresponding with a Mistress D on a fetish lifestyle web site I found, her profile said she was into a switch mistress and enjoyed forced feminization, CBT, Bondage, etc. The usual thing you see on the web sites for mistresses. She also was bi-sexual and was into "switching players", and expression that I had never seen before.

After a few months of exchanging emails, me telling her my fantasies and her controlling my excitement at times, she agreed to meet with me as she put it "see if I deserved to serve her in person".

We agreed on a Thursday session, she sent me her address with directions and instructed me to arrive at her address at 8:00 am. Being new to this I thought it odd for such an early appointment, after all I though most sexual activities occurred in the evenings. Still to me that appeared to be very early, but what the hell since this was the first time I was going to serve a mistress I didn't know what to expect. Looking at her address and the directions she gave me I figured it would take about an hour for me to get to her place.

I left my house early, kissed my wife and "went to work" as usual. I got off the State Highway at an exit near her town which was about a mile from her address at 7:15. Not wanting to appear too anxious I stopped at a Starbucks and had a cup of coffee to kill 30 minutes. Leaving Starbucks I navigated through a nice residential neighborhood turning onto her street I was getting nervous. Arriving at her address at 7:55 and rang the doorbell.

Mistress D answered the door wearing a very fluffy pink robe and black thigh high boots. She asked who I was, I answered as she instructed " I was her slave and there to serve as she desired". She smiled and let me in, I handed her the "GIFT" that we agreed upon as she led me to the kitchen area. Smiling she asked me if I'd like a cup of tea. Not waiting for a reply she poured a cup of tea and put it in front of me. Telling me to drink it, it'll help relax me. With her watching me I sipped my tea. She then said "drink it we don't have all day", so I did. I took a big gulp of the tea; she smiled and said she was going to get changed and that should I relax and not be so nervous. Take my coat off and hang it up in the closet.

I started to feel very relaxed and was feeling very horny, my thinking that it was me actually going through with meeting a mistress. I sat at the kitchen table and finished my tea as she returned wearing a black corset that pushed her gorgeous breasts up in the half cups exposing her large nipples, black sheer stockings and at least 4 inch high heeled bright red shoes. Looking at her I couldn't help but get excited, her perfect breasts pointing right at me and with her exposed smoothly shave crotch my cock was rock hard. I was feeling a little light headed as she suggested that we begin. She instructed me to take off my clothes, place them on the chair and follow her to her play area. I removed all my clothes and followed her down the stairs to the basement. Reaching the bottom of the stairs I saw she beauticians' makeup table with two chairs.

Telling me that if I was to serve her as her slut I needed to dress the part, she went to a small cabinet and took out a corset, walking over to me she wrapped the corset around me and began pulling it tight. I could hardly breathe as she said this will give you a nice curvy shape. As she tightened the corset around my midsection, it pushed my chest out. She finally stopped tightening it and tied it off, leaving me taking shallow breadths. Then she took my hand and led me to a small bathroom with a shower in it, she said that first thing we need to do is to make me presentable. She applies some lotion to my legs, around my cock, balls and ass stroking my hard cock as she did this. After she finished rubbing onto my legs she told me raise my arms, as she coated my arms, underarms chest and back with the lotion, she then told me to lower my arms. She then told me to wait here as she stepped out of the room to make a phone call. Standing in the shower stall with this lotion all over my lower body, everything started to tingle, she returned about 15 minutes later and said "time to rinse". Not knowing what to expect, she turned on the shower and told me to get in. As the water started cascading over my body my hair was coming off with the lotion, looking at her in shock she laughed and said I told you we needed to make you presentable didn't I. As the water washed away all the hair below my neck leaving me leaving smooth all over. Instructing me to turn around she sprayed my ass and more hair washed down the drain. She then told me to spread my legs and hold put my hands against the wall leaning forward bending at the waist. She then took a tube and stuck it up my ass, pouring warm (what I thought) was soapy water up my ass. Laughing she said "this mix make my insides as clean as the outside". I was then told to sit down and shit out the liquid, she flushed had me stand again, bend and more "water" pumped up my ass, after doing this three or four times (I lost count) I was very light headed and as she said all nice and clean in and out. After having me dry my legs off with a towel and rub some moisturizing lotion on my legs, ass and around my balls she lead me out of the bathroom and to a makeup table. She then pulled out a chair that was on casters, in the center of the chair a dildo stuck straight up; she took a tube of this lubricant and squeezed a good amount on the top of the dildo. Smiling as she stroked the dildo, she said I should take my seat.

Still feeling a little light headed and extremely horny I moved over to the chair, turned around and lowered myself slowly onto the dildo. She started laughing and pulled me back onto the dildo, driving it into me in one motion, making sure that the dildo was all the way in. She then took what looked like a seatbelt and wrapped it around my waist securing me to the chair. Rolling the chair to the table she told me to put my hands on the table and to insert my finger into what looked like gloves with the fingertips cut off. As I slid my fingers into the gloves I noticed that the gloves were secured to the table. She then took a metal (what looked like a C clamp) and put it over my wrist and into guided it into a couple of holes in the table, pushing down on the clamps they clicked into place locking both my wrists to the table with my fingers stretched out flat. She then smiled and said that NOW we will begin with my transformation.

She sat opposite me and started applying fingernail tips over my fingertips and then poured some clear liquid on them telling me that all sluts need to have nice long nails. She then proceeded to apply makeup on me. She picked a deep red stain lipstick and said that this lipstick would be the perfect color for me. Applying the lipstick she then leaned over and gave me a deep kiss. Smiling she suggested that she highlight the edges around my lips and told me shut my eyes as she finished up with my lips and applied eye makeup. My lips tingled from the lipstick, she told me to relax and make a wide "O" with my lips pushing them out so she could finish up with the pencil lip liner. As I did this she pushed a 2 inch penis gag into my mouth, I felt something against my lower lip as she pulled a cord over my head securing the gag in my mouth. My eyes shot open looking at her. The penis gag in my mouth was complete with balls that pressed against my lower lip. How am I supposed to use my safe word with a gag in my mouth I wondered? She laughed and said that now the fun begins.

Walking around the table she took some lotion and rubbed it on my chest, as she did this she told me that all good sluts need to have a nice pair of tits. Telling me that the lotion was a moisturizer that will help loosen the skin on my chest she walked over to a cabinet and got what looked like a hard clear plastic bra with tubes coming out of the tips. Inside the bra cups were needle in each cup, she came over placing the bra over my chest and securing it in the back and over my shoulders. Taking the other ends of the tubes she inserted one tube into a pump of some kind. As she did this she explained that she wanted me to experience being a real slut and that she wanted me to get "real" tits quickly. The bra cups with the needles would inject saline into my chest , taking a quart bottle of saline she hung it on to a hook next to the makeup table letting the liquid drip into the needles in the bra cups. She pressed a button on the table and a pump started sucking my chest into the bra stretching the skin. As my new "breasts" expanded the needle pushed into my nipple and she then opened a valve on the saline line it started flowing into my chest. Laughing she said not to worry that anything she does to me will only be temporary and that this is only the beginning and not to get too comfortable. She had more to do before my transformation was complete.

Rubbing some lotion on my cock she slipped a cock ring over my cock, with a vibrator on it, another ring was pulled through my balls and a sleeve was pushed over my cock, the sleeve also had a tube coming out of it that went to another pump. The pump had a tubes attached to it one came from my cock the other went to a small bottle she held up and hung on a rack next to the saline liquid. Another tube ran from the bottle she pushed into the back of the balls attached to the penis gag in my mouth. Pressing another button I then felt my cock being sucked, after a few moments being so horny I started to cum I saw the cum getting sucked into the small bottle and the liquid mixing with my cum start to flow into the balls attached to penis gag in my mouth as the gag started to get larger in my mouth almost gagging me the penis gag then started to spray liquid into my mouth. She had this smile on her face and said: "Don't worry sweety, like I said nothing is permanent". She explained that my body would absorb the saline tits over the next few days and that the liquid being mixed with my cum would not only tighten my vocal cords giving me a nice high feminine voice but also keep me horny and willing to so anything for at least several hours. She continued explaining that the tea she gave me had drugs in it, a mixture of Viagra and Ecstasy along with a little herbal stuff to make me horny and very open to any suggestions made. The idea was to keep me hard and horny for the boys to play with for the next few hours. I looked at her in a panic; she laughed again and pushed another button causing the dildo in my ass to pulse up and down. As she walked over to a big screen TV on the wall I came again spraying more cum and drugs into my mouth. She turned on a Transgender domination movie and said that I should enjoy the movie until company arrives. She then went upstairs for a few minutes leaving me there with pulsing dildos in my mouth and add, my chest being sucked and filled with saline and my fingers getting long fingernails.

After what seem like forever I came for probably the sixth or seventh time, she walked down the stairs pulling a wraparound red dress over her corset and holding my wallet. She tool out my driver license and said that she'd be back in a while with my wife. Still feeling light headed she started to turn off the toys. Removing the bra with the needles from my now "C" cup tits she tweaked the nipple I moaned.

She then told me that the saline mixture had female hormones along with some other "FUN drugs" In it, making my new tits very sensitive, she rubbed them again as I came again. She then turned off the cock sucking device and removed it and the cock rings from my still hard cock. She laughed saying that the drugs will keep me hard for the next few hours, but not to worry that she had some friends coming over that I could use me for entertainment and that I would be very satisfied when they were done. Unstrapping me from the chair she has me stand, my ass stretched from the dildo in my ass, she then tells me to put on the high heel shoes and to lock them on. The doorbell rings, I'm told to go upstairs and answer the door. Dressed like a hooker, Naked wearing high heels, long bright red nails a blond wig makeup a very stiff cock and TITS I go upstairs. She follows me and as I answer the door she introduces me to these three guys. She tells me to entertain them, telling the three guys that the video is all set to record, and to make it good.

They all three say "YES MISTRESS" together. I'm lead to a bedroom, the three guys strip and tell me to bend over the edge of the couch as one shoves his cock in my ass the other puts his cock in my mouth. For the next few hours, I'm pounded by cocks. Being made to suck cock after it's been in my ass, lick their asses and every time I cum, they have me lick it up.

As Mistress leaves she tells me that she will be back soon and that my wife will be joining her. Saying that since I had told her that my wife didn't like sex with men, maybe she'd prefer women and she was going to help her learn how to satisfy a woman and they would be back in a few hours.

I was left there being fucked silly by the three guys as she left the house laughing. In less than 3 hours, I'm turned into a stoned, horny shemale with tits, getting fucked and sucking cock for a video that's being recorded to a computer. The worst part is I'm so horny I keep cuming and sucking more cock and I was enjoying it.

PART Two:

Mistress D had transformed me into a slut and turned me out to entertain her friends as she leaves to go to my house.

Mistress D puts my address into her GPS and takes a back with some toys with her along with some "special" homemade cookies and brownies. She pulls up in front of my house, fixes her coat and goes to the front door. She rings the doorbell, my wife answers and mistress tells her that her cell phone went dead and her car stalled. Asking if she could please use the facilities and make a phone call. My wife Mary being innocent, lets her in and hands her the portable phone. As she comes in mistress notices that my wife has her girlfriend and her 26 year old daughter with her, they are having coffee.

Mistress pretends to call a car repair service, she asks my wife what the address is and she relays again pretends to relay the information to the car towing service, as she hangs up she says great they're going to be about an hour before they get there.

My wife offers her a cup of coffee and introduces herself and her girlfriend Donna and her daughter, Laura to mistress. Mistress says she would love a cup, and she has an idea. She runs out to her car and returns with the box of cookies. Telling my wife that she was going to a meeting and since she's not going to make it they may as well enjoy the cookies. Mistress then asks her where the restroom is, handing the cookies to my wife. My wife takes the cookies places them on the table and shows her the restroom, down the hall. As mistress goes into the restroom, my wife opens the cookies and puts them on the table. As she puts them on the table, the three take a brownie, as soon as they finish one they take another. Saying that these are really good cookies.

A few minutes' later mistress returns with her coat over her arm looking at the three women at the table. She asks if they're enjoying the cookies, they say yes. Mistress takes her coffee and sips it sitting down; she offers another cookie to each of the three women. The three now glassy eyed women start fidgeting in their seats. Mistress then says that it's a little warm in here, do you mind if I make myself comfortable. Mistress then stands and unties her wrap around dress taking it off, revealing her corset, stockings and boots. Her nipples are sticking out and her smooth pussy is moist with anticipation of what's to come.

The three women stare at her, getting aroused, she asked if they like what they see. The three nod yes without moving from their chairs. Have another cookie and then we can have some fun mistress suggests. Each of the three takes a cookie and devours it, staring at mistress. Mistress opens her bag and takes out three eight inch dildos and says that we're going to play a game. The first one to put the dildo in their mouth all the way in wins, the only thing sticking out should be the base and the balls; she only has two prizes so they'd better not cheat. She places the dildos in front of the women and tells then that they can begin when they are ready. Laura takes the dildo and slides it right down her throat without even a slight gag, mistress laughs and tells her that she's done this before. She then tells her to hold it down her throat; mistress takes a cord and wraps it around her head holding the penis down her throat. Telling her to get up and mistress will give her, her prize in the next room. Mistress tells the two older women, Mary my wife and her girlfriend Donna to keep trying and that the winner should tie it off with the cord on the table. She'll be back for the second place winner in a few minutes; she has to give Laura her prize.

She leads Laura into the living room, still gaged with the dildo down her throat, she takes off her blouse and pants, removes her bra but leaves on her underwear. She opens her bag and takes out a couple of vibrating eggs, she slips two of them into Laura's' wet pussy, and slips a small vibrator plug up her ass, adjusts her underwear and puts wrist cuffs on her behind her back having her cross her arms behind her back she then clips the wrist cuffs to nipple clamps that are dropped over her shoulders. As she lower her hands behind her back, she pulls her nipples up. Smiling she asks the Laura if she's comfortable, the 25 year old is not but nods. Now let me see " mistress says" that she's almost ready. Leading the 25 year old back to her mother Donna who now has a dildo down her throat.

Mistress smiles as they walk in, the two women at the table seem concerned that the young girl is being hurt, but mistress says. Don't worry about her, she's having a great time aren't you sweetie? The girl moans as mistress turns on the three vibrators (2 in her pussy and the plug in her ass). She drops to her knees and moans pulling her cuffed wrists tugging on her tits. See mistress laughs saying that "she's having a ball".

Now Donna you seem to have won second place. Mistress tells her to raise her arms, and mistress pulls her blouse and bra off. Telling Donna to get up mistress opens her pants and lowers them taking off her underwear also. Donna (my wife's girlfriend is now naked in the kitchen with a dildo tied down her throat as her daughter is busy Cuming from the three vibrators buried inside her. ) is told to have a seat and slide forward, mistress secures her ankles to the back legs of the kitchen chair, her exposed pussy at the edge of the chair taking her arms, she cuffs them behind the chair back.

My wife Mary in the meantime is still working the dildo into her throat, finally getting in. Mistress says about time you downed that dildo. She removes the dildo from my wife's mouth and tells her to strip. She removes her clothes without question. Mistress tosses a pillow on the floor in front of Donna and tells my wife to kneel and to get her girlfriend off.