Is It Punishment If You Enjoy It

INTRO

I'll start my story by saying I don't know why I do what I do. I had a loving family and went to the best schools and never wanted for anything growing up. Now I find myself at 35 years of age, with a $50 million dollar fortune left to me by my parents and I spend my nights working as a prostitute. I obviously don't do it for the money, but selling my body gives me a thrill in a way that mutual, consensual sex just can't seem to do.

At night, in the dyke bars downtown, I am known as a whore that can be bought for the evening, but no one suspects that, during the day, I am managing a small real estate empire. When I go out for my extracurricular evening activities I generally dress rather cheaply, and provocatively. You know.....like a slut. At 35 I like to think I am not unattractive and have been told by many "clients" and others that my Nordic features and blonde hair are striking and my athletic 5'10" frame doesn't hurt either. I work hard to stay in shape at a gym whose membership probably cost more than most of my clients make in a year. My 145 pounds look good on my tall frame and the 38c breasts aren't bad either. I haven't seen so many years yet that they have started to sag and the small rings piercing my nipples draw a lot of attention.

The bar owners know me and why I am there. I have to give kickbacks to most of them, but it doesn't matter since I am not really doing it for the money. Some of the female bar owners prefer to take their cut in "trade". I'm sure the male owners would like to as well but that has never interested me. I have known I was a lesbian through and through since I was in junior high school and experienced my first communal shower after phys ed class. I had a few love interests in high school, but all of them were bisexual at best, and even though they were curious about touching my body, they weren't ready to accept being a lesbian. So it wasn't until college that I really had a true girlfriend, Nadine. She was a couple years older and much more experienced with women than I, but I was a fast and eager learner. Neither of us were what you could call shy and we experimented with all kinds of sex. But even though we were eager and willing, we didn't know enough to really delve into how deep our sexuality could go.

It wasn't until Nadine had graduated that I began to see how deep the rabbit hole could go. I was asked to stay after class by one of my instructors to talk about my grades....which weren't all that good. At that time I had a bit of a rich kid mentality and had found more interesting activities than doing homework and attending classes.

Once the classroom was empty Ms. Richardson said she had noticed Nadine and I and that there might be a way for me to improve my grade. I wasn't so naive that I didn't immediately get what she was hinting at, but I later realized that I didn't fully understand her meaning. Ms. Richardson wasn't unattractive but she was nearly 30 years my senior and, college professors not being known for their fitness, was a bit overweight and wore very conservative, almost shapeless clothing. I really didn't care about my grade, but I was very interested in seeing what might come of her offer. I told her I would do whatever it took to get a good grade and she wrote an address on a scrap of paper, passes it across to me and told me to be there at 7:00 the next evening.

I spent the next day and a half running though scenarios in my head. But mostly I assumed I would show up at her house, lick her pussy a bit and get an A. I couldn't have been more wrong. But that's all a story for another time. The short version is she opened the world of sex to me and jumped in with both feet. What I hadn't counted on was that I didn't get a free pass on my grades just because I was offering up my body to the teacher. What I got instead was tutoring from Ms. Robinson and her friends. They taught me economics and history and literature and if I did well, they taught me about bondage, and sex toys and consensual sadomasochism.

PART I

Its Friday night and I am getting ready to head down to Patty's Place. Patty is a 50ish bull dyke who dresses in leather and always takes her cut in trade. She is nothing that anybody would call pretty but she has a presence that makes up for her physical limitations. She could probably bed most of the women who visit her place but she seems to take a particular delight in fucking me when she thinks I owe her. And technically I do owe her. I let two women hire me out of her place for an evening last weekend and I hadn't been back around since to settle up. The women paid me $500 so I owed Patty $125 or an hour in her office bent over her desk taking her strap-on and sucking her pussy. The longer I made her wait for her money, the harder I was going to get fucked. What Patty didn't know was that I had made her wait a week on purpose so she would be the mood I wanted her to be in. Many of the women who I let take me home just want to lick my pussy, or have me lick theirs and then cuddle for an hour. But, some, the ones I try to seek out like things a little more interesting.

Threre are about a dozen regulars that live their sex lives a little closer to the edge. Like Jessica who is a house wife by day, but when her husband is out of town, she wants me to bath her and worship her feet, then give me a golden shower before making me lick her to orgasm. Or Monica who is into rope play and likes to practice her shibari skills to a more extreme degree than her lover can appreciate. She likes to tightly bind my breasts with rope, tie me into some painful contortion and then masturbate as I struggle against the bindings.

But tonights fun will have to start with Patty and me pretending to be scared of what she is about to do to me. The more I act afraid, the more Patty likes it and the harder she goes at it.

I start getting ready about 7:00. Making sure my pussy is freshly shaved and I am clean inside and out. Tonight I put on a faux leather skirt that comes to mid-thigh with no panties underneath. I add a gray tank-top, short leather jacket, and short black boots. I drop a little cash into a small clutch along with a small (by my standards) anal plug and some nipple clamps. A little mid-market perfume and I am ready to go. I climb into my 6-year-old Toyota I use to keep up appearances and head to Patty's.

I park around back and try to slip past the bouncer un-noticed, knowing the whole time I can't and that he will probably immediately notify Patty of my arrival. He lets me go past, but I have barely taken a seat at the end of the bar when I feel someone press up against me and a hand slip around me to roughly take hold of my right breast and squeeze it roughly. Without letting go of her grip on my breast, she hisses in my ear, "My office, now!". I mumble something about being sorry and that I meant to get her her money and with my eyes downcast, head toward her office. More than one woman in the bar who has been on Patty's debt at one time or another sends a knowing glance my way. But their sympathy is wasted. Little do they know; this is exactly what I have been waiting for all week.

As soon as were through the door she grabs me by the back of my neck and pushes me toward her desk. I start to apologize but she tells me to shut the fuck up, she doesn't want to hear it. She is just going to take what is owed out of my ass. I know what's coming next and bend over her desk, spreading my legs slightly. She moves up behind me and kicks my feet wider apart while reaching for the office phone. She tells the person on the other end of the phone to play something with a heavy beat and turn it up.

I can hear her opening the filing cabinet drawer where she keeps her toys. I hear the now familiar sound of the strap-on being buckled around her waist and then her hands at my ankles, spreading them wider as she uses leather straps to secure my ankles to the legs of her desk. Over the thumbing bass of the house music, she nearly has to yell "Want to see what I got just for you? The last time I had to remind you about paying me, you looked like you might have enjoyed it". Which wasn't wrong. She had fucked me in the ass for a solid 20 minutes with a strap-on dildo that was easily 10" long and over 2.5" thick. I had orgasmed at least twice from the pounding and after she was done was wobbly on my feet for a few minutes after she roughly shoved me out of her office into the waiting eyes of the bar's patrons. I had made my way to the first stool I could find and sat down with a very contented look on my face that some may have misinterpreted.

I felt her move up behind me and the weight of something heavy being flopped down on top of my ass. From the weight of it, it felt huge. She pushed her hips back and forth, sliding the rubber dick along the crack of my ass. "I don't think you will be smiling after this you slut". And from the fact of how far I had felt the dildo slide up my back without her hips touching mine, I knew it had to be at least a foot long or longer. I was starting to feel the beginning of a little fear mixed with my excitement. I have an experienced ass....very experienced in fact. But Patty and her giant phallus might give me more than I had bargained for.....but maybe exactly what I craved. and I wanted to make sure I got what I wanted.....needed. "Please, Patty, I'm sorry. You know I was going to pay you", I pleaded. "Well after I am done, you certainly won't ever forget again", she replied. "Please don't make me take it in my ass", I begged. "Shut up, bitch. Now I am going to show it to you so you know what's coming."

I heard her walk around the desk and suddenly my vision was filled with the image of the biggest strap on I had ever witnesses. It looked fully 15" long and as thick as my clenched fist.

I had been fisted in my ass before, but that is different than taking a dildo of this massive girth. When getting fisted, the wide part of the hand only takes a second to slip past the anal ring and then the wrist is narrower and more manageable. Even when being repeatedly fisted, the stretching only lasts a short while. If Patty starts that massive cock into me, it will go deep, probably deeper than I have ever experienced before, and it probably won't come out for many minutes. I began to feel the first tightenings of fear in the pit of my stomach. But despite the fear, I wanted it. I knew this was going to hurt but I needed it more than anything else in the world at that moment.

Patty saw the fear. Probably the first time she had seen real fear on my face. and she laughed to herself and said "I have been looking forward to this". The giant cock slid out of my view and I heard her walk back around the desk. She said "I am not a completely heartless bitch", and I felt a cold glob of lube hit my ass crack and felt her shove at least 3 fingers roughly inside me. The suddenness of it made me cry out a little and Patty seemed to enjoy it. "That's right bitch. And there is so much more coming".

I felt her left hand on my hip and then the head of the giant dildo was against my sphincter and the pressure started. I felt her slowly lean into me. My asshole spreading and spreading and still the head want inside me. "Time to teach you some respect, bitch" and with a hard thrust of her hips forced the head of the cock into me. I wasn't ready for it and the pain was overwhelming. I know I must have screamed but I can't remember doing it. I had my eyes clamped shut, but lights flashed in my brain. Time passed, but I don't know how much. The next thing I remember was Patty screaming "Take it slut. Now you will respect me!" I let out a small moan, that's all I could manage.

And she said "stop your whining! We have only just started. And I felt the pressure start again. My ass was screaming at the intrusion but I was starting to accept it. Every inch she pushed into me elicited more groans but I still wanted to take more. My mind was screaming, but under the screaming was a voice wanting more. I wasn't coherent enough to know if I actually said something or not but Patty said "Want more slut? Well, you are going to get more!" And I felt pressure deeper inside me. I felt my sphincter being stretched but now there was a deeper feeling. Deeper than I had ever felt before and still her hips weren't against my ass! I couldn't do this, couldn't take more. But still I wanted to. Patty wasn't giving me a choice though.

The pressure continued and the pain increased. I am sure I was screaming and panting between the screams. I think I begged her to stop, but I knew she wouldn't.....hoped she wouldn't. I felt the first stirrings of the orgasm at the edge of my consciousness. I saw a small, bright light far off in my vision. The harder and deeper Patty pushed brighter the light got. Then finally, blessedly, I felt her hips against my ass and the head of the monster cock was hitting something deep in me and I was thrashing on the desk, my legs straining against the leather straps and I was screaming and screaming as the orgasm washed over me in a flood. I don't know what happened after that, but the next thing I remember in Patty looking into my face saying "You fucking bitch slut. You enjoyed that!.