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Gambling Less Than Anonymously


I arrived in Tampa looking for a fresh start. I had just gotten out of my second toxic relationship in a row. I seem to be an expert at attracting troubled women and seemed to be destined to live a lonely and turbulent life. Despite feeling newfound freedom from the second toxic girlfriend in a row I was also lonely and horny. Fortunately one problem that I didn't have was money. I had been a successful entrepreneur and made big bucks in selling my company at the ripe old age of 33, and now primarily was a hands-on philanthropist working for many worthwhile causes. I was staying in a hotel until I could locate a suitable property to buy.

I had travelled to Tampa from Jacksonville not only because things that I had read and otherwise found out about the city were intriguing, including extremely worthwhile philanthropic endeavors, but also because I still had unresolved issues with my second-to-last ex. Bridgett Swanson - the name I knew her by - was beautiful and charming, but I found out after only six months with her that she was a gold-digger; actually more than that; she was a con artist and bookie (or at least her boyfriend - who I never knew about until later - was). While she may have had some feelings for me, they were definitely shallow. I caught her cheating and stealing and booted her out.

After I booted Bridgett I found out that she had stolen about $25,000 worth of jewelry from me. I got an arrest warrant issued for her as well as a default civil judgment. I carried the arrest warrant with me along with a fake bounty hunter's certification from the state of Florida. I had gotten information from a private investigator that Bridget, under another name, had set up shop in Tampa and being a hands-on guy with a concealed carry permit in Florida I wanted some retribution.

Since I had not yet used the information I had to track Bridgett down, imagine my surprise when on only the third night of my arrival in Tampa as I was simply walking from my hotel to a local restaurant I ran into my second-to-last criminal ex Bridgett. I followed her to a fairly secluded part of a downtown street near the Lightning's hockey arena and then confronted her.

"Hi Bridgett darling," I smirked.

She tried to get away but I was on her like stink on shit and forcefully restrained her. "Let go of me now or I'll scream," she yelped.

"Go ahead, sweetie," I snarled. "I have a copy of your arrest warrant and a copy of my bounty hunter's license in my sport jacket pocket. If you scream we'll just wait here until the cops arrive at which point you'll go to jail now with no hope of escape. If you come with me to talk who knows - we might be able to work something out. You know that hope burns eternal in the human bosom."

I really wish that Bridgett wasn't so good looking because my cock betrayed me and saluted, and even more importantly I wish that I wasn't a gentleman; I would have loved to smack her around for cheating on, and stealing from, me.

She knew by the determined look in my eye that I wasn't fucking around.

"OK," she said. "Where to?"

"Where can you afford to pick up the tab for dinner?" I snickered.

We went to a local version of the Olive Garden - she was cheap besides being slutty - and sat as far away from the rest of the patrons as we could.

Once we sat down - with her further from the door than I was so that I could prevent her escape should she try it - I showed her the real arrest warrant, my real civil judgment, and my fake bounty hunter's certification.

"Why in the hell did you get a bounty hunter's certification," she snickered. "You run out of money?"

"No, I have plenty of money, no thanks to you," I snickered back. "I got it only because as you know I'm a hands-on guy and I wanted to legitimately be able to bring you in on the arrest warrant should the possibility arise."

We ordered dinner - no alcohol for me but she needed a stiff drink - then I interrogated her. "OK, here's the information I have about where you live now and with whom," I said. I gave her bullshit information. "Is that right?"

"Yeah - how did you find out?" she replied, lying through her teeth.

"Bridgett, you're not going to get away with your normal lies and cons with me. The information I gave you was bullshit. Get out your identification - all of it - and show it to me."

I could tell that she was selectively rummaging in her large purse so I yanked it away from her and went through it myself. I took photos with my iPhone of all of her cards - even a library card - and her two different driver's licenses, one in the name of Bridgett Swanson, the other in the name of Constance Danner. "Another felony or two Bridgett sweetie," I chuckled. "Which is the real ID, and which is the false I. D.?" I asked.

She didn't answer, but sat with her arms crossed.

"I'm sure that you don't have a permit for this COP 4," I continued as a confiscated the exotic four barrel derringer that was in her voluminous purse.

She continued to sit stone faced with her arms folded, but clearly winced when after unloading it I stuck the derringer in a coat pocket, and continued rummaging through her purse.

"OK what is your real address - and you better tell me the truth because we're going there after our reunion dinner, and if I find out that you lied to me things will be bad for you, and whatever low-life you're living with now," I seriously stated. I took that opportunity to expose the gun in my shoulder holster to her.

The address she gave me was a condo in Ybor City which seemed legit but that I would find out about for sure later than evening.

After that we actually chatted like two old friends while we ate dinner, had dessert, and coffee. I mostly told her the truth about my life, although I doubt that she was truthful with me (especially "I regret cheating on you Blake; I should have known a good thing when I had it"). She especially liked the fact that when I told her about my most recent ex that it was clear that she was a significantly more treacherous bitch than Bridgett was - although thankfully not a criminal.

Bridgett reluctantly paid with a credit card - one of her pieces of her IDs that I had taken a photo of - and I was pleased to see that it wasn't declined. As we exited the restaurant I clicked a pair of handcuffs onto her right wrist and my left one. "What's that for?" she snarled.

"I don't want any possibility of getting separated from my previous true love until we get to your abode - I told you that I'd be checking it out," I chuckled.

We were basically silent in the taxi on the way to her condo. I guess she really did live in Ybor City because she had a key that actually opened the front door. I drew my Browning P-35 Hi-Power handgun (I like exotic guns too) in case Bridgett's boyfriend was around - I knew she must have one even though she denied it. "I told you that I live alone," she snapped when she saw my drawn P-35.

"You also told me that you loved me, so forgive me if I'm not entirely sold on your honesty," I snapped back.

After going through all the rooms on both floors of her small condo, and not only finding no one, but no evidence that there was someone living there besides her, I holstered the P-35. "Let's sit down and talk about how you're going to make things right with me Bridgett dear," I said, pointing to a small couch.

"Are you going to give me my gun back?" she snipped.

"Probably not - but we can negotiate almost anything that you would like."

She broke out a bottle of wine, which I declined, but which she ended up consuming entirely over the next two hours or so. Our conversation wasn't too productive until she got a little looped, after which she did open up about some assets. She had sold the jewelry she stole from me - and had not gotten full value for it - but it was obvious that she was at least a successful bookie if not con artist. I finally got about $10,000 worth of cash or valuables out of her. She either didn't want to give me more, or didn't have more, because then she tried her sexuality.

"Look, Blake; I really don't have any more valuables, but I don't want to go to jail. We were always good together in the bedroom. How about you take the rest that I owe you out in trade on my body," she cackled as she slithered over toward me on her hands and knees and ran her hand over the crotch of my pants, which was barely restraining my disloyal cock.

I knew that the bitch would probably kill me in my sleep, plus I really, really needed to be over her as surrogate for all of my exes, so I politely - then forcefully after she kept stroking and almost caused me to pop my zipper - declined.

She sat back in her chair and sulked for a few seconds. "You're obviously fucking horny and desperate for my pussy yet you push me away?" she rhetorically snapped.

"I need to get past you and all of my exes," I retorted "and need to get a different type of woman. If you've got nothing else maybe we should just go to the local precinct," I replied with a shoulder shrug.

That panicked Bridgett; "No wait...wait..." she pleaded. Her mind was obviously churning. Then she seemed to have a Eureka moment. "You want good relationship material; what if I fix you up with a perfect woman for you? What would that be worth?"

"Sorry to insult you, dearest, but it's hard to believe that you know someone who would be good for me..." I started to say when she interrupted me.

"Wait - I have a photo of her on my phone," she said, reaching into her purse and pulling out her android. After a minute or so of swiping she enlarged a photo and said "Here she is."

It obviously was a candid - not a posed - photo that the woman in the photo probably didn't even know was taken. I have to say, though, that even if it wasn't the best photo that she was obviously plasma hot. Also, she looked normal as far as her makeup, dress, and whatever demeanor can be gleaned from a photograph, was concerned.

Bridgett could tell that I was intrigued. "You'll either have to find a call girl or it will take you months to find worthwhile relationship material in Tampa, Blake; I'm offering you something better."

"Maybe she won't like me..." I started to say as my pea brain turned things over in my mind.

"I've got a deal. What if I guarantee that she'll fuck you bareback within the first week that you know her, and that she'll be your best fuck ever? If she is you write off $1,000 of what I owe you for each sex session with her, and $2,000 if it's your best ever, until I work off the rest of the $15,000. Then you get the arrest warrant rescinded and have the civil judgment marked satisfied."

She could tell that I was seriously thinking about it. "What have you got to lose?" she continued.

"Are you her pimp?" I asked, half seriously, have humorously.

"She's not a call girl, I swear. She might require a no STD certificate from you though if you want her bareback, and I can arrange one for her. She's had bad luck with men, but you'd be right for her."

I was getting more interested the more I viewed the mystery woman's photo. Bridgett cinched it with "I'll agree to a lien on my condo and car; I'll go to the courthouse with you tomorrow."

"OK...OK...OK..." I finally stammered.

This led to another surprise, however. As we went through Bridgett's papers in her strong box looking for the condo deed and car title, I came across a birth certificate in the name of Julie Thorsness. The condo deed was in that name, although the car title was in the name Constance Danner, the second of her driver's licenses in her purse.

"Do you even know who you really are?" I asked.

She simply smiled, and shrugged.

After I put the deed, title, and birth certificate in my jacket pocket I said "If you need to use the washroom do so now, because I'm handcuffing you to your headboard and sleeping on your couch tonight."

She started to protest but knew that it was futile.

Bridgett/Constance/Julie went into the bathroom and returned naked - she looked just as good as the last time that I had fucked her, and my cock again had a traitorous response. "Are you sure you don't want to sleep with me in my bed?" she cooed.

"I'm sure," I growled, then insisted that she put on a nightgown and handcuffed her to her sturdy metal headboard.

"What if I have to pee in the middle of the night?" she snickered.

"Just call out to me - I'm leaving the door to your bedroom open - and I'll uncuff you," I replied as I turned to leave.

My sleep was fitful - the only way I got to sleep was thinking about fucking the woman in the photo!


The next morning we ate breakfast at a local IHop while I called various law offices in town until I found a woman who seemed that she could handle what we wanted, and who was available. About 11:00 a. m. we met with Sally Pingree, Esq., and I explained what I wanted done - liens of $15,000 on each of Bridgett's car and condo. Sally raised her eyebrows when she saw that they were in different names, but didn't consider that a problem. "I assume that you are Julie Thorsness aka Constance Danner" was her clever response.

"Yes, that's it," Bridgett nodded with my approval.

Bridgett signed the documents that Sally prepared and Sally promised to have them recorded that same day. While Bridgett went to the washroom I had a heart-to-heart talk with Sally, and made sure that only me - not Bridgett - was on her retention agreement. When Bridgett returned I paid Sally and then took Bridgett to lunch.

"Can I have my gun back?" Bridgett asked as soon as we ordered.

"Why?" I inquired.

"Because my job requires me to go to some bad neighborhoods, including tomorrow, and you don't want anything bad to happen to me, do you?" she grinned.

"Bad assumption," I snickered. Then she gave me a vulnerable look that she used with success on me when we were together. "Is it registered?" I asked.

"No," she replied.

"Why not?"

"I just didn't bother."

"Let's go to the courthouse and get a permit for you, then I'll return it," I said.

She shrugged her shoulders, we had an otherwise normal conversation, and then we went to the courthouse together. She produced another driver's license in the name of Julie Thorsness, and with that and the deed to her condo she was able to get the proper forms filled out for a concealed carry permit. While it would take several months to issue, I returned the derringer to her, and separately the bullets, when we parted ways at the courthouse steps.

I gave Bridgett the name, address, and phone number of my hotel, as well as the room number; and got her phone number in case I purchased a house before her friend contacted me. "Get the STD clearance within the next few days, and I'll have my friend contact you within the week," were Bridgett's parting words.

I was almost as horny as I had ever been when Bridgett's friend called me five days later. "Hi...Blake...uh...this is Bridgett's friend Brenda," was her nervous introduction. That is the first time that I even heard a name - Bridgett had refused to give it to me.

"Hi Brenda...thank you so much for calling. Bridgett has told me so many nice things about you that I feel that I almost know you already," I cheerily replied.

Even though I'm terrible at picking women to have relationships, one thing that I am good at is small talk and setting people at ease. After a fifteen minute phone conversation Brenda did not seem nearly as nervous, and seemed anxious to meet me that night.

"Do you want me to pick you up in a taxi?" I asked.

"Uh...no...no...no," she stuttered, her nervousness temporarily returning. "Can I just meet you at your hotel; I'll come up to your room so that you'll recognize me, and me you," she continued.

"Sounds good; see you at 7:00 p. m.," I cheerfully signed off.


I admit to a little trepidation myself when I was getting ready for my date with Brenda. While I put little stock in Bridgett's honesty, in her photo Brenda did look like she could be a normal woman - just what I needed after my last two toxic relationships. I was pleased when I opened my hotel room door to a knock at almost exactly 7:00 p. m. when Brenda looked even better in real life than in her photo. The only odd thing was that she had what looked like a gym bag in one hand; I assumed she might have just come from working out.

We exchanged pleasantries for a couple of minutes, then I said "Let's go out to dinner and then decide what to do after that."

Brenda looked a little surprised, but said "Uh...sure."

"You can leave your gym bag here if you want, or with the concierge in the lobby," I said, pointing at her grip.

"Uh...I can leave it here," she said, plopping it down near the door.

In many ways Brenda was the most desirable woman that I had ever met in my life. She was intelligent, knowledgeable, and effervescent, in addition to her world class beauty and poise. However, she also had a nervousness and what may have been a lack of self-confidence - I couldn't tell for sure - that I found bizarre given her numerous attributes.

We had an enjoyable dinner; Brenda did excuse herself just before dessert to make a call outside, and returned with a smile on her face - although there was no doubt that the smile was forced, and she was clearly down emotionally for the next ten minutes or so. After I paid the check we went to a dance club and had a great time - she was a wonderful dancer, and really loosened up, no trace left of her malaise after her phone call. Finally we took a late night walk arm-in-arm.

About midnight I said "Do you want to come up to my room to get your gym bag, or can we arrange to meet tomorrow night and I can bring it to you then?" I asked, as a way of getting another date. That seemed to really take her by surprise.

"Uh...why...why don't I come and get it tonight," she stammered.

We rode the elevator to my hotel room, and when we got inside things really got weird. It was like she was timidly expecting me to have her stay the night. After a few minutes of discussion during which she hemmed and hawed I finally asked "Is there something wrong?"

"Uh...I have my STD-free certificate right here," she said, reaching into her purse and handing me a piece of paper that looked just like my STD-free certificate. "I promised Bridgett that I'd try and be your best ever; even if you don't like me, can you give me a chance?"

"Stuff like this doesn't happen in real life" I said to myself. Of course being a horny, single, red-blooded male I would have loved to take this goddess to bed immediately; however, I had been playing it cool because I was interested in a long-term relationship not a one-night stand. Her words, and accompanying nervousness, were blowing my mind - and inflating my cock at the same time.

Things were resolved before I could verbally respond when she approached me and gave me a passionate full mouth kiss at the same time that she stroked my rigid cock through my pants. Regardless of my plan to play it cool, there was no way possible to pass on this opportunity.

We quickly disrobed, but just before I carried her to my bed she nervously mumbled "Bridgett said that you'd show me an STD-free certificate too."

"Uh...sure," I replied as I quickly went to a dresser drawer and pulled it out. She looked at it for only a second, and then tossed it aside and jumped into my arms.

Naked her body was even more spectacular than it looked clothed. Everything about her was breathtaking, from the conicality and firmness of her tits, to her oversized hard nipples, to her sleek thighs and the open triangle between her thighs and pussy, and to her pulsating slit with oversized clitoris.

After we rolled around a while in my bed with our bodies plastered against each other, with unexpected strength she flipped me onto my back and then shinnied down to my crotch. Her tongue, lips, all ten fingers, and even her nose contacted and excited my cock and both testicles. Her mouth and hands moved seamlessly and fervently between my cock, one testicle, and then the other. She had me ready to erupt within two minutes flat, but there was no way that I wanted to waste a load.

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