I Never Thought Id Be Her Bitch Pt 01

The papers arrived Friday, it was all official, I was a free man.

It was like my stay of execution had been approved by the governor, and it read like a Shakespearian play. "The petitioner is hereby granted a final divorce." The formality of the word alone, petitioner. Nate is granted a divorce, its Nate baby, I'm finally free! I laughed out loud.

I was enjoying my view from the 11th floor of my brand-new apartment. The city below was mine for the taking now, or at least all the single women in it. Life was good. Especially when I'd spent the past year living at my pussy whipped brothers house.

I love him dearly, but it was far from ideal. He was stuck in the same kind of "roommates" marriage I just got out of, only he didn't have the balls to become a "petitioner". It was selfish, but I was glad I didn't have to witness him suffer anymore.

With my newfound freedom, I decided it was about time to get back out there and see what my options were for finding a sex partner. I wasn't ready for a "girlfriend," or any kind of commitment. I was also aware after 20 years of missionary once a month, my skills weren't exactly sharp anymore.

The mirror wasn't as kind to me as it was 20 years ago either. I was reasonably fit, but my hairline was receding, and I wasn't that tall to begin with at 5'5. My body was average, and my desk job and genetics limited my masculinity. I kept myself well-groomed and dressed to compensate for it. I recently shaved off my beard in an effort to look younger, and bought some very modern clothes, just in case I actually got a date.

I knew the world had changed, and on-line was how people met these days. I wasn't a high-tech guy, but I managed to get tinder on my phone, and wrote a less than spectacular personal profile. It was a start. I spent lots of time swiping left and right, fascinated by the concept of looking at a woman's picture, and swiping right if I wanted to fuck her, and left if I didn't.

By the end of the first week, I had a few messages, but most were "hello" or "hey there" with nothing happening when I responded to them. I was starting to lose interest in the monotony of it all, when my phone beeped and there was a Tinder message, "Do you have a big cock?"

Initially, I went to delete it, but I wasn't getting a lot of interest, so I wanted to at least try a reply. The first problem is, I don't have a big cock. In truth is I am smaller than average, and I know it. I told women it was over 5 inches, because I had spent so much money trying to make it longer. I tried creams, pills, fancy lights, and even manual stretchers. In the end, I was just under 4 inches when I was rock hard and that would never change.

I found the message, and with nothing to lose I sent a simple reply, "no." Just to see what would happen.

To my surprise, I got an almost immediate response, "I want to meet."

I wasn't expecting a response, let alone an offer to meet. I clicked on her picture to have a better look at her dating profile. Her photo was reasonably sexy. She looked around 40 years old, with long dark hair. She wore black rimmed glasses that gave her a sexy librarian vibe, with deep red lipstick. It was a waist up photo, so not much more to go on, other than the opening in her blouse which showed she did have ample breasts.

Her dating profile was brief:

Elizabeth Missy. If you are boring, move on. Sex only, no commitment. Serial players and alpha males note I'm smarter than you, and not an insecure bimbo who needs to believe your lies. Unemployed, live with your mom or heavy drinker? I don't do losers. Size matters bigger isn't better, if you're man enough, I can prove it to you.

"Bigger isn't better?" I thought out loud. "I'd like to be way bigger."

I was intrigued now. I replied, "What did you have in mind?"

Within 15 minutes there was a reply, "Crown and Castle, 65 Smith at Main North, 8pm - Missy."

8pm? That's only an hour from now. I thought she must be really fucking horny! I googled the address, and it was 40 minutes away. I'd have to leave in soon if I wanted to make it. I thought about it, was I really going to run right over there on the strength of 2 short messages? I looked at her profile again. There was a chance I'd get my dick wet, better find my keys.

I got there in 35 minutes, my heart racing just like my car was on the way. I hadn't met a woman for sex in over 20 years, so I wanted to get there early. The bar was an elegant, traditional upscale British pub with tin ceilings and lots of oak. The tables were arranged like chess board pieces on a black and white tile floor. A huge bar dominated in the center. I looked around to see if Elizabeth was there already but didn't see her.

I sat at a table with a view of the door and ordered a beer. Looking at the clock it was 7:55, so I got out my phone and tried to waste a few minutes. 10 minutes later, I was starting to wonder, did I get the address wrong? I checked; I was at the right place.

20 minutes later I thought she must have been delayed, I sent her a message on tinder, no reply. 30 minutes later, I asked for my bill and prepared to leave. I felt so stupid for going there and letting myself become sexually frustrated so easily.

While chastising myself in my head for being so desperate, Elizabeth appeared at the door.

She was about 5'3 with dark hair in a ponytail. She was wearing a black leather jacket and skirt that accented her curvy but still very sexy body. Black pantyhose with a sparkle and deep red shoes finished the polished look. As she got closer, I recognized her black librarian glasses, and I stood up as she got to the table. I gestured to her seat and we both sat down.

She had great brown eyes and long lush eyelashes, and her lips were a deep red like her shoes. Her teeth were bright white, and she reminded me of Anne Hathaway when she smiled.

"Elizabeth, is it?" I asked.

"It is for now," she replied.

I wasn't sure what that meant, so I tried something else.

"You must have gotten delayed?" I spoke.

"No, I got here exactly when I should have," she replied.

I thought to myself, she's a fucking nut case. If she wasn't hot, I'd be out of here already.

"Why did you want me here so early?" I asked getting a bit impatient.

"To see if you would be here on time, and how long you would wait for me. Lots of men are unreliable, impatient or can't follow direction. If you respect me, do what I say and are prepared to wait, I'll give you all the sex you can handle," she replied.

She said it so confidently, I was temporarily speechless.

My mind was trying to understand what it all meant, but it was distracted by her saying "I'll give you all the sex you can handle." Did that mean she wanted sex with me now? I was hopelessly unprepared for a woman like this, so I just blurted it out, "Do you want to have sex?"

"That's why we're meeting isn't it, to have sex?" she replied, matter of fact.

Now my mind was swimming. Don't fuck this up I thought.

"Do you have somewhere we can go?" I asked.

"Aren't you going to by me a drink first? I'm not a whore." she said.

"Oh, sorry," I said sheepishly, "I'm not sure how this works."

"You mean don't know how to respect a lady?" she questioned.

"I'm divorced," I replied, immediately thinking what a stupid thing to say.

"It's easy to tell," she laughed, thankfully the waitress came to take our order.

I told the waitress, "I'll have a beer and?" I waited for Elizabeth to make her order.

Nothing.

"Elizabeth, would you like a drink?" I asked her.

"That's better," she said "I'll have a Manhattan and he'll have red wine."

"I was gonna get beer," I said, looking at her quizzingly.

"If you want sex later, you'll have wine, beer makes cum taste like soap." she replied firmly.

The waitress was clearly amused by Elizabeth's response.

"I guess it's red wine then sir," the waitress said. A huge smile was on her face.

"I looked at her a bit bewildered and said "Yes, red wine will be fine."

After the waitress left, I asked Elizabeth, "Can you at least explain what you want from me?"

"It's pretty straight forward," she said "we meet for sex when and where I tell you. You miss a date, it's over. You don't play by the rules, it's over, you get boring, it's over."

"Play by what rules?" I asked.

"I'm the one who's going to be making sure your cock is happy, I make the rules as I go." She smiled and watched the waitress cross the room with our drinks.

"Manhattan, for the lady," she said "and red wine for," she paused, "later."

Elizabeth and the waitress exchanged big smiles, like they had an inside joke before she turned and went away again.

I was trying to process it all, did she say, "make sure your cock is happy?" Was I going to get my cock wet tonight? I trained my eyes on the cleavage between her tits then slowly up to her mouth. My cock tingled; it had been a very long time since my cock had been sucked.

I took a sip of wine, looked at Elizabeth and said, "good choice."

She replied bluntly, "Tell me how big your cock is."

Her questions were still alarming to me. I looked around the room, leaned forward, "Under 5 inches," I whispered.

"How much under 5 inches?" she asked.

"It's almost 4 inches when it's hard," I whispered.

She was clearly turned on by answer. Her body language changed. "Your cock is going to be sucked well tonight." she said. She was getting a bit flush in her cheeks.

"How big is it when you're soft?" she asked.

Normally I would be terrified of telling a woman these details, but her body language told me it was a sincere turn on for her.

"Maybe an inch" I told her.

"That's perfect, we should get out of here," she said, "drink up."

I took a big gulp of my wine, "where are we going?" I asked.

"I have a spot across the street." she said.

She started to get up and I fumbled for my wallet, throwing a 20 on the table. She looked at it and shook her head, I added another 10.

I followed her out of the bar and down the street a short way, we crossed over the road and into an apartment building. Once in the elevator I got a good look at her from the ground up.

Red platform heels and black nylon covered legs and were a good start. The tight leather skirt gave her a great shape and the leather jacket had an air of authority. The deep red lipstick on her mouth was such a turn on. My heart was pounding now, and my cock was beginning to get hard.

We got down the hallway, and she used her key card to open the apartment door. Inside there was black leather furniture with a red carpet with chrome tables. The artwork on the walls all depicted naked women of some kind. It felt like a high-class gentlemen's club.

She led me down a short hallway, and into a bedroom. The light was dim, but I could see a bed on one side and mannequin standing on the other, it was holding a tray with sex toys on it. My mind was racing, "holy fuck, I've hit the mother lode." I thought.

She sat on the bed cross legged and told me to undress. I started taking off my shirt as she watched intensely. When I started unbuckling my belt, I asked her "What about you?"

"I don't need to be naked for you to get your cock sucked, Natalie" she said."

Natalie? What the fuck does that mean? Too horny to care, I dropped my pants and lowered my underwear exposing my semi hard cock. She smiled widely when she saw it. She stood up and took some leather gloves off the tray.

Once she pulled them on, she reached out and stroked my cock a few times. "It's so beautiful" she said.

I stood there in my socks as she stroked me and it felt amazing, I was getting harder fast.

"Completely naked Natalie," she said.

I awkwardly took my socks off, still trying to fuck her hand as I did.

She led me by the cock closer to the mannequin so she could reach the restraints that were lying on its tray. One by one she started putting restraints on my wrists and ankles. I thought this is so kinky. She went back to stroking my cock and I was dying for her to blow me.

The last restraint went around my neck. I was a bit nervous when she was putting it on, but I relaxed once she was done and focused on stroking me again.

She backed me against the wall between the bed and the mannequin and I heard a click as one wrist was clipped to a ring on the wall. Then she did the other wrist, followed by both ankles and my neck. My cock was so hard from the stroking, precum was freely leaking out onto her glove. She smiled and started milking my cock roughly with her other hand to get even more of it on her glove.

Once her glove was covered, she went back to the sensual cock stroking I loved. She seemed very pleased and brought the glove up to her face to admire it. She turned in in front of her face and looked like she wanted to lick the cum off it.

I was shaking as my orgasm was building and I was thrusting my little cock into her hand. I was so hard now; my balls began to ache.

"Look how dirty you got my glove" she said.

I didn't respond, it had been a long time since anyone had touched my cock and I was lost in forgotten pleasure.

"You got my glove dirty" she said again, this time letting go of my cock and wrapping her hand around my balls.

"Don't stop" I said, my hips grinding my cock into the air now.

"Clean my glove, Natalie" she ordered, giving my balls a squeeze.

My thrusting slowed and I looked at the glove, it had my pre cum on most of the fingers and the palm. She brought it closer to my mouth. I couldn't move my head away due to the neck restraint.

"Clean it." she said firmly.

I had never tasted my own cum before, this whole experience was way beyond anything I had ever done sexually. I looked at the liquid on her glove, then at her face. She started using her fingers to tease my cock again, it felt very good.

"Clean it or it all stops." she whispered...

Fucking crazy bitch! I thought in my head. I tried to move but the restraints were too tight, I was helpless. I didn't want to stop, it felt so good. She gently began to stroke my cock, while gesturing her hand toward my mouth.

"Clean it, Natalie!" she demanded. She let go of my cock slapped me in the balls hard.

I don't know if it was the shock of the sharp pain in my balls or her loud voice ordering me to do it but I gave in. I licked some cum from her leather covered fingers. She began sensually stroking my cock again.

"There's is nothing more satisfying than watching a man eat cum," she said as she gave me a quick kiss on the lips. Her body twitched with excitement, and she quivered for a moment before resuming the sensual stroking of my cock.

I had never tasted my cum before, or any mans for that matter. The salty silk liquid ran down my tongue and onto the back of my throat. There was a slight soapy taste and I wished I wasn't a beer drinker for a moment.

I imagined that every woman who ever sucked my cock knows what this tastes like. She turned her hand as I cleaned to make sure I got it all, clearly pleased with my submission to her.

She got close to my ear and whispered, "Swallow it, Natalie."

I knew she was trying to feminize me. Calling me Natalie and making me swallow my cum. My cock felt so good in her hand and the thought of swallowing my own cum was so very erotic. I didn't want to submit further to her, but something inside me snapped. I swallowed deeply and showed her it was gone.

"What a sexy bitch you are Natalie," she said. "You earned a treat."

Reaching in her skirt pocket with one hand, she pulled out a condom, and tore it open with her teeth. She kneeled and stopped stroking me long enough to roll it on. Then she started licking the tip of my swollen tiny cock with her tongue.

I was a disappointed that she made me wear a condom, but her tongue felt amazing. My cock had gone so long without oral; I was in heaven. She opened her mouth and teased that she was going to suck it. I wanted to grab her with my hands, but my restraints had me pinned.

She looked up at me. "You don't have control of your body anymore" she said.

She grabbed my balls with one hand and continued to lick the head of my condom covered cock. The sensation sent shivers up my back, and I moaned as my legs began to twitch as my orgasm got closer.

"You don't get to cum yet," she said as she stopped licking my now throbbing cock.

"Do you want it sucked?" she asked.

"Yes, oh fuck yes I do." I was pleading with her.

"Without the condom?" she asked.

"Yes, yes, please." I was pleaded.

"Are you sure?" she smiled, "There's no turning back."

"Yes, suck my cock, please suck my cock." I answered. I was going crazy with anticipation.

"You're a good bitch," she said."

She pulled off the condom and left my cock throbbing in the wind.

"Ok, Crystal," she said "You can take his essence now."

I thought "Who the fuck is Crystal?" When the mannequin began to move.

When it stepped out of the corner, I could see it better. It was dressed in a hot pink latex rubber body suit with huge breasts and nipples. Its hair was pulled back in a tight ponytail with a rubber face mask that was tight on its head. There was a pink latex skirt around its waist and the legs were tight pink latex with white cotton frilly socks on their feet. Black platform stilettos clicked the floor as it walked toward the bed to set down the tray.

I was in shock and said, "Who IS that?" I said shakily.

Elizabeth started to stroke my cock. "Does it matter?" she said.

My head was swimming with too much pleasure I was so horny. It was erotic overload; I couldn't resist anymore. "No" I said.

"Crystal, kneel down and make him release his seed into your mouth. Show him how much pleasure a well-trained bitch can set free." Elizabeth said.

Crystal knelt and I immediately felt a warm mouth wrap around my cock. I was in heaven. She took every inch of me from the start, her tongue licking my whole shaft at once. As she alternated between deepthroating and circling their tongue around the head, I knew this was the best oral of my life.

I felt her hand come up and start to massage my balls as she continued to overwhelm me with sensual sucking. The technique was amazing from flicking their tongue in and out of the tiny hole at the end of my cock, to licking my balls as they took me deep again, she held my hips and drove my cock deep into her mouth. I had never been sucked like this.

When she felt me get close to cumming, they slowed down and when I wasn't on the edge, she worked harder to get me there. The sound of slurping and swallowing filled the room, it was the most erotic sex sounds of my life.

"Ok Crystal" Elizabeth said "Take him over the edge and claim your prize."

Elizabeth let go of my hips and reached for something on the floor. I heard what sounded like a tube being squirted. Crystal was sucking me harder now and I was aching from being hard so long. I could feel her hand on the inside of my thigh now and I was so close to orgasm.

I felt the cold of lube touch my balls then fingers sliding further up. My mind cried out, "No!" but my body never moved. Her finger was circling my anus, covering it with slippery silk lube. She teased the opening and rubbed it harder. My mind screamed out "You shouldn't enjoy this," but my body kept moving until their fingers were directly on my opening.

Suddenly, she slipped a finger deep inside me. It was like pressing a button. Cum shot out of me like I was putting out a forest fire. My whole body spasmed and jerked. I heard Crystal gagging as I filled their mouth with gush after gush of cum. She kept trying to suck me, but there was so too much cum. She struggled to breathe and some cum dripped out of the corner of their mouth onto their skirt.

As my orgasm died down, Crystal stayed still and let me pump the last few drops of it inside her, while gently spasming from trying to continue fucking her mouth.