Blessings and Fulfillment

It had been well over a year since the last time I had been home. This time, I was not the hot shot computer programmer with the sexy girlfriend anymore. You see, I had been "down-sized" at work six months ago and because I had not found a high paying job fast enough, Carla, my girlfriend of three years, had left me.

After she left me, I realized that she had only been with me for my money. All the good times and kinky sex we had were just a means to an end for her. She just wanted my money. Well, the joke was on her, I was not as broke as she thought I was. I got a much better severance package than she thought I had gotten. Plus, I had a very large stock portfolio and savings accounts that she did not know about.

Now I know why such a sexy woman would want to be with a perverted computer geek like me. I thought that I had died and gone to heaven when I met Carla, so sexy and eager to join me in my kinky ways. See, I am a submissive bisexual crossdresser who loves tight bondage and stern discipline by both Masters and Mistresses. Carla seemed willing to do anything I wanted, with anyone I wanted to.

The only reason that Carla had entered my dark, kinky world was because she thought I made six figures. Well, I may be a pervert, but I am not stupid, Carla only thought I made six figures, when I was really making seven figures without my bonuses and stock options.

When Carla and I were together, we lived in my house in the woods where I had my office. Being a computer programmer, I worked at home and very rarely went into the office. The location let us do anything we wanted to without anybody seeing us.

Most of the time I was dressed as a woman and the people in town thought that I was a real woman. Being a small guy does have its advantages, I am five foot six and only one hundred twenty pounds. I even let my red hair grow past my shoulders and my fingernails grow long. I even bought a very good set of C cup breast forms that I could glue to my chest. With those breast forms I could go braless without anyone knowing they were fake tits.

About once a month I would treat myself and Carla and we would go to a small beauty salon to get our hair and nails done. The salon was run by Master William, and Carla and I had many wonderful scenes with him. Master William is a tall, good looking man, about six foot two, one hundred ninety-five pounds with sandy blonde hair and a goatee. When I was in his salon, as a customer, I was treated like the lady I looked like, but other times I was his sex slave.

In fact, when I was "down-sized" that is where I worked. I was the shampoo "girl" and I worked for tips. When Master William would find me in the back room, he would fuck me or have me suck his ten inch cock. This was OK with Carla, because she got to fuck Master William and anyone else, she wanted to.

Many times, after we had our hair done at Master William's salon we went to his house where they would fuck each other while I was tied to a chair, unable to do anything but watch them. When they were done fucking, I would be released so I could suck Master William's cock clean then eat his cum out of Carla's pussy.

Only two weeks ago, after we had our hair done at Master William's salon we went to his house and went straight to his bedroom. There I was chained to a hard, straight backed wooden chair as I had been many times before.

With my arms twisted behind the back of the chair where my wrists were bound together, and my ankles pulled back and attached to the back legs of the chair spreading my legs wide open. This time my skirt was pulled up and my cock was pulled out of my panties.

While Master William was chaining me to the chair, Carla was doing a slow, sensual strip tease in front of me. When she was naked, she sat down on the edge of the bed and started to finger her pussy telling me just how much she loved it when a real man fucked her. I watched her slowly slide three fingers in and out of her wet pussy as she pinched and tugged at her big, fat nipples.

Carla said, "only real men can fuck this pussy", and she was right.

I had not fucked Carla in over two years. For her, Master William, or some other guy that she picked up got to do that, I just got to lick her pussy clean after she was done. Many nights Carla and I would go out to the clubs, with me dressed as a woman, just so she could pick up a stranger to fuck.

We would discuss the possibility of how these men in the club would be as sex partners for her. Then she would pick one, or more, of them and then take them back to my house where she would fuck them while I was in next room listening to their moans of lust and when she was done with her "stud of the night" she would have me lick his, or their, cum out of her pussy while she told me just how good of a lover her stud had been.

As Carla teased me by fingering her pussy, Master William shoved a large penis gag in my mouth and tightened it around my head. Carla told me that I was "nothing, but a cock sucking, cum drinking, dress wearing, faggot that could never please her". Carla then undressed Master William and they climbed on the bed.

Master William then took some pillows and placed them under Carla's ass to raise it up. This was something that he had never done before. Now, with her ass raised up high, he climbed on top of her and from my chair I could see his ten inch cock, shiny with Carla's pussy juices, slowly slide in and out of her wet pussy, causing her to moan and scream with lust.

After Master William had cum in her pussy he climbed off of Carla and walked over to me and instead of releasing me to clean them both up, he just wiped his cock, covered with both of their juices, all over my face and told me "that the best was still to come". With that Master William pulled on a pair of silk running shorts and left the room.

After he left, I looked over at Carla to see her, with her legs still spread, slowly fingering her freshly fucked pussy. While she was fingering her pussy she noisily sucked on her cum covered fingers then told me that I was a "useless faggot that could never please a woman" and that she was "going to be pleased tonight".

At that time Master William walked back into the room. I was stunned to see a line of ten naked men standing behind him. I thought that I was going to have to fuck and suck all those men while Carla and Master William watched. Carla explained to the men that she was my girlfriend and I was "nothing, but a cock sucking, cum drinking, dress wearing, faggot that could never please her" and she wanted to show me "just how real men pleased a woman".

Then the men started to climb on to the bed, one at a time, with her and started to fuck her. From my chair I could see their hard cocks pounding into Carla's pussy as she fucked them back. As they fucked I could see her fingernails raking their backs, her legs wrap around their hips, her ass humping to meet their cocks, and hear her lusty grunts of pleasure as she lost herself in all of those cocks, causing my cock to get bigger and harder.

As she fucked those men one of them noticed my tiny cock and said that they "could see why she needed them to fuck her" because I truly was "nothing, but a cock sucking, cum drinking, dress wearing, faggot that could never please her" and that I was enjoying watching the fucking Carla was getting from all of these men as much as she enjoyed getting fucked by them.

Most of the men fucked her at least twice; some even fucked her three times. When the last man had fucked her, she reached between her legs and pinched her pussy lips together. Master William then unchained me from my chair and ordered me to lie on the floor. As I got on the floor, he removed my penis gag and when the men saw my gag they laughed at "the sissy cock sucker". Then they lifted Carla off the bed, while she pinched her pussy lips together, and they carried her over to where I lay on the floor. The men lowered her pussy right over my face while one man forced my mouth open.

With my mouth wide open, Carla released her pussy lips and all of them cum flowed out of her pussy right into my mouth and I swallowed it all. Then I tried to lick the last drops of cum off her pussy lips. The men laughed at me as I stretched my tongue to get those last drops of their mixed cum clinging to her pussy lips. As I was trying to lick those last drops of cum from Carla's pussy lips, all the men there were laughing at me, calling me names like "cum sucker, panty boy, and a wanna be lesbian". It was true, every last name they called me.

Then they lifted Carla up to her feet where she wrapped her arms around two of the better-hung men there and stepped on my rock hard cock. She ground her foot into my cock and balls causing me to wince in pain and pleasure. Then she pushed even harder with her foot, this caused me to cum all over her foot.

One of the men told me to lick my cum off Carla's foot. I quickly got to my hands and knees then I licked and sucked my cum off of her toes. When I was done a different man pushed me back down to the ground with his foot. I looked around and saw that all the men, but the two that Carla had her arms around, were gone.

As I laid there Carla looked down at me and told me that we had just had our last date, she was leaving me for her two new studs. Then they turned, leaving me laying there on the floor, laughing at me, walked out of the room.

For a long time, I just lay on the floor, I could hear some laughter in other parts of the house, then nothing. After about thirty minutes or so I got up and slowly walked out of Master William's bedroom, to look for Carla.

There was no one in the house so I got my purse and walked out to my car. I was so nervous as I drove home; I was not sure if Carla was just trying to scare me or not when she told me we had just had our last date. When I got home, I realized that she was telling the truth, all her things were gone. Her closets and dresser were empty, her wall hangings, and artwork taken off the walls, everything of hers was gone. I had been dumped by my sexy, kinky girlfriend.

I fixed dinner then went to bed, Carla's and my bed. It felt so empty without her there with me. The next morning, she was still gone, so I got ready for work as always. I put on a short tight red knit skirt and sheer, white silk blouse that Master William loved me in. Under that I had on a red lace bra with matching bikini panties and a black lace garter belt with black silk seamed stockings and four-inch black patent leather pumps.

When I got to Master William's Salon, he told me to go in the back room and get wait for him. I quickly went to the back room, with the other hair stylist watching and snickered at me. They knew "what" I was and what Master William did to me when he caught me in the backroom, but I did not care. I was there, in the backroom, to please Master William, not those catty jealous women out front.

When he came into the back room, he ordered me to suck on his ten-inch cock, as I did, he told me that he had not washed it since he fucked Carla the night before. Then he had me bend over his desk where he pulled my skirt up, my panties down and fucked me in my ass. After he had cum in my ass, he, with me lying across his desk, catching my breath, he told me that I was fired, that he had replaced me as his "shampoo girl".

As I walked out of his salon all the hair stylist laughed, out loud, at me, they knew that I had been fired. I drove slowly home, thinking that how, in the last twelve hours, I had lost my girlfriend and my job. What a pathetic loser I was.

While I was sitting, all alone, at home the phone rang. Grabbing it, hopping it was Carla, I answered in my sexiest voice to find that it was Tim, my best friend from back home and he wanted to talk to Tom, the "male" me.

I almost blew my cover and reverted to my male voice, but I told Tim that I was "Katie the housekeeper", and that "I" would be happy to take a message for Tom.

He told "Katie" to tell Tom that he had called and to call him back right away. After I hung up from Tim, I decided to call him back in a few hours.

While I was sitting at home, alone, I was thinking about the last three years with Carla and realized that the only reason that she had been with me was for my money. Well, I still had my money in the bank, and she did not get that much money from me.

After sitting there for about an hour I stripped and walked outside to soak in the hot tub. As I sat in the hot tub I looked down at my fake "titties" and could not help but to play with them. Oh, how I wished that they were real.

After a long soak I got out, went inside, and put on my red silk robe, fixed my make up, then I called Tim back. All Tim wanted to know, at first, was if I was fucking "Katie" or not.

I told him that "Katie" and I did have sex a few times a week, and Carla knew about it and even sometimes joined in for a "three sum".

Tim was speechless, here I was, a computer geek, getting two sexy women at the same time in bed with me. As we talked we decided that I needed to come for a visit, and Tim quickly decided that we needed to get all of our friends together and go out to all of the strip clubs in town, like we had done in the past.

Being alone and jobless, I told him that I would drive into town, get myself a hotel room, and meet him after work on Friday.

After we hung up, I made my plans and hotel reservations for myself and my "wife". I would leave early on Friday morning so I could get my hotel room and change from a sexy woman to a male computer geek before I met Tim after he got off from work. On Friday I put on a denim mini skirt and thin white tank top and a pair of black patent leather pumps with four-inch heels, then I packed a bag with my male clothes and a few of Katie's clothes. Putting the top down on my car, I headed off to meet Tim.

Along the way I let my skirt ride up and quite a few truckers got to see lots of my thighs. One lucky trucker got a real eye full, I noticed that he had matched my speed to look at my legs so I twisted in my seat and pulled my tank top up to show him my braless titties at him. Judging by the look on his face he liked what he saw, and he never knew they were fake tits glued on to guy's chest.

The driver motioned me to follow him, so I pulled in behind his truck and as we pulled off the highway at the next exit, as he went right, I went left. Knowing that I was not the kind of "girl" he thought I was I could not chance stopping and doing anything with him. Quickly I saw a large shopping mall and decided that would be a good place to stop, stretch my legs, and go to the bathroom.

While I was walking around the mall, enjoying the sound of my heels on the floor and the men staring at my braless tits, I saw a lingerie Shoppe. Looking around I saw a sexy black leather bra, bikini panty, and garter belt set that I just had to buy.

The leather was buttery soft, and I do love the smell and feel of leather. Adding a pair of seamed stockings to my leather lingerie finished my shopping. Paying for my purchase with "Katie's" credit card, I then headed back to my car.

On the way out of the mall I stopped in the lady's bathroom so I could put on my new lingerie. Even after spending most of the past three years dressed as a woman, I still find it a thrill to walk into a woman's bathroom especially when real women were already in there.

As I walked in, I noticed that two stalls were occupied. Walking into an empty stall I put on my new lingerie. As I stood there, in a bathroom stall, in the lady's room, in my new leather lingerie, I just had to masturbate. As usual, I caught my cum in my hand and then licked my hand clean. After getting redressed, I fixed my make up and went out to my car.

By now my trucker friend should be long gone, so I would not have to worry about him when I got back on the highway. Soon I was back home, heading for the hotel, and becoming a male computer geek once again. When I went to check in the desk clerk, an exotic looking Asian woman, asked me if my husband was with me. I told her that "Tom would be here in a few hours", and to let him know that I was already here.

The bell hop who took my bag to my room was checking me out as we rode the elevator to my floor. After he opened the door for me I put my foot up on the corner of the bed to "fix my stocking" so he could see the lace top of my stockings and a bit of my upper thigh.

When I tipped him, I noticed that his cock was growing, and he told me that "if I needed anything, 'anything' at all, just ask for Bobby".

The bell hop may have been a wimpy looking teenager, but it was fun to tease him like I had. I thought that if I was a real woman, I might take him up on his offer. Hey, even wimpy teens need to fuck too.

After Bobby left, checking the time, I saw that it was time to "put Katie away and become Tom" once again. When I had removed my tank top and skirt, I walked over to the full length mirror and looked at "Katie" standing there in "her" new leather lingerie. DAMN, I did not want to change back into Tom; I wanted to be "Katie" forever.

First thing I did was cut my fingernails and remove the polish. Now I had to take off my new leather lingerie. I put all of "Katie's" clothes away, and then I removed my breast forms and put them away also.

Heading to the bathroom, I took a long, hot shower to remove my perfume and make up. After my shower I dried my hair and put it in a ponytail, because I could always say that it was the "fashion" for the computer geeks where I worked.

My male clothes felt so uncomfortable and strange to me because the last time I had worn them had been six months ago, when I had to go into the office for work. I had to remember to walk like a man not like how Katie walked, with her hips twitching back and forth. Now it was time to meet Tim and the rest of the guys.

Because we would be drinking, I had the front desk call me a taxi, which was waiting for me when I got downstairs. When I got to Tim's office all the guys were there waiting for me. We decided to start by going to dinner at a local seafood restaurant that we use to hang out at.

Everything I did, walking, sitting, and even eating I had to remember that I was dressed as a Tom not Katie and that I had to act like a man. After dinner we headed to the adult entertainment area, where I was shocked to see that it had shrunk from five blocks down to almost three blocks since I had been here last, but most of our favorite bars were still there.

We started at one end and started to make our loop, having a beer in each bar, watching the women dance and play with themselves on stage. As we bar hopped, making comments about the women dancing on stage, I kept looking at what they were wearing, their makeup, shoes, and their bodies, not because I wanted to fuck them but because I wanted to look like them. No! I wanted to be them.

While I was there, I had to remember that I was dressed as a guy, so I had to act like just like my buddies. When the dancers came by our seats, I had to tip them by sliding my dollar in their panties, just like everyone else did. It did let me get a closer look at those sexy thongs.

Every time, at every bar, that I did that I wished that some strange guy was sliding a dollar in my panties after I had danced for him. Hell, lots of people had seen me naked, fucked me, been flashed by me, like that trucker this morning, and I had even danced for Master William, Carla, and some of their friends many times in the past. The difference was these dancers were real women and I was just a pretend one.

At one bar I asked Tim if the "Gypsies" were still in the next block or not. Tim said, "their whore house is still in the same old spot".

Their sign in the window said "fortune teller" but everyone said it was a front for a whore house, but I was never sure. The women that stood just outside the door, though very beautiful and sexy, did not wear skimpy, reveling clothing like the women standing outside of the strip clubs and other whore houses in the area.