Fucktoy Jen

This story is a little long, but it is mostly true. It's a story about sex, love and reconciliation and how I dealt with a changing relationship and one I ultimately didn't want to lose.

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I met Jenny innocently enough on a motorcycle blog. I have been riding for most of my life and have a number of motorcycles, so I'm on all the sites, usually to offer free (but bad) advice. Now, these blogs are generally guy only sausage fests, but she apparently wanted some advice about how to prevent her butt from getting sore on rides, using the pen name 'Seraphina'. So, I weighed in with some bad recommendations, as did about a hundred other guys. What set my post apart was that mine was respectful. I hit the "post" button and thought nothing further of it.

A week or so later, I get a note in my blogsite inbox. Surprisingly enough, it was Seraphina thanking me for the tip. I replied accordingly and she responded with one of those happy face emoji things. I posted nothing in return because I didn't have much else to say and my go to emoji is the steaming pile of dog shit with the smiling eyes, which I didn't feel was appropriate in this case. So, once again, I thought that was the end of it. She was nice, though, I thought to myself later.

Another week goes by and I had another email from - guess who? Seraphina and, this time, it was a long one. I guess she was on the site to meet somebody which was perhaps not surprising in retrospect. Ok, so what's going on? I dig in.

The gist of her rambling word salad was that she was divorced, between relationships and was looking for a bit of casual fun. No, not that. The motorcycle ride kind of fun. She thought I was nice and probably not an axe murderer, so she asked me. I explained she was wrong in that I am not nice and I was currently studying to be an axe murderer, but I still hadn't passed "sharpening". Somehow, she thought that was funny, but I refrained from hitting on her further. Let's let nature take its course. She lived about fifty miles away, so I agreed to the ride.

She also noted in the email about how old she was which, interestingly enough, was not far from where I was. I do like older woman because there's less bullshit. They know what they want, they know how to get it and they are upfront about it. Perfect. Let's ride.

What Seraphina didn't know at the time, however, was that not only do I like motorcycles, I also like bondage sex. This was the primary reason behind my split with wifey. I liked it. She didn't. Ok, not all the time and nothing too serious like with needles and poop, but come on. Show me something different once in a while. Just a little. Nope. Not gonna happen.

The whacky thing in all this is I built from the ground up a dedicated playroom in the house for the activity. We used it for vanilla, but not much else and this became the Great Divide for us. Oh, well. Ok, I get it now. Kind of a shame, really, because wifey had great tits and I had plans for those things. Like clothespins and rope.

So, I meet Seraphina on my bike, an old BMW, at which point she notes her name is "Jen". I asked her if that was her real one or if she was between names and if I should be ready for another one next week. "Ha, ha, no, that's my real name." Ok, Jen it is. She was a rather skinny redhead with no tits, but kinda cute with a nice smile. I didn't need the hassle of a supermodel anyway. Likes pot. OK, a little wild, I thought to myself and I couldn't help but wonder if the curtains matched the carpet. She was living with "a female friend" in an apartment in a rather shaky part of the local city, but nothing I hadn't ridden in before. It was a crappy ride out of town with all the traffic and I took her to a little outdoor place just outside the city. She seemed to like being on the bike.

Jen likes to talk and talk about herself, so I just let her go while I took it all in. Usually, my narcissism takes over and all I do is talk about myself, my motorcycles and my alpine rides but, amazingly, this time I kept my mouth shut. I found it's a good way to learn something. Reading between the lines, it became clear that not only was Jen between names, she was also between money. I don't think I have ever met a woman who had her own money. It was always "her family's", "her husband's", "her rich uncle's" etc. Never their own. I don't know, I'm not rich, but I have some money. My own money. I made it. All by myself.

The conversation then devolved into a discussion of relationships and, ultimately, to sex. Shortly thereafter, I realized I should have continued to keep my mouth shut. But I didn't. I told her how horrible I was with relationships and where I was now and why.

"When was the last time you had sex?" Jen asked.

Oh fuck, I knew she was going ask that one, I thought to myself.

"I don't know. A couple months ago, I think. I really can't remember." I responded. "I'm not even dating that much. It's hard to meet somebody in the garage."

She laughed. "Do you like sex?" Jen pushed further.

Is she fucking kidding me?

"Well, yes. That's a stupid question!" I blurted. Given my situation, the last thing I needed was a psychoanalysis.

With a snarky smile, she leaned into me from across the small table, lightly grabbed my hand and asked:

"So, why don't you come over and fuck me?"

I sat there in a bit of shock, looking at her, saying nothing.

This stuff never happens to me.

"Well?" Jen asked

Now totally nervous, I stammered: "Now?"

In a completely calm and reserved manner and with a little smirk, Jen replied: "Why not?"

What was even more shocking was I was almost thinking of excuses not to take her up on her offer. But then I started coming around as a horny guy that hadn't had sex in months. OK, game on. You want to fuck? Perfect. I'm your guy.

"We don't really know each other that well, dear," leaving her an out. She didn't take it.

"You don't have to marry me; you just have to fuck me," Jen said, still smirking.

Well, ok then.

As it turned out, Jen was a fuck machine. She loved to fuck. And suck. No tits, but she had the best rear end and set of legs. She will sit on your face and demand you make her come. Yes, the curtains did in fact match the carpet, which was a tiny vertical wisp of red hair. She suffocated me for probably an hour with her pussy and she didn't care. She wanted the "O".

"Lick it. Bite my clit." She moaned as she came with my hands all over her beautiful ass and my face covered with pussy juice.

Then, she got off my face, turned around on all fours, smiled and said "FUCK ME". In fuck mode, she's a machine, an appliance and the encounter got more active and rougher as we went. I pulled her shoulder length dark red hair while fucking her hard from behind and she simply asked for more.

"Fuck me harder, what's wrong with you?" She commanded.

I was trying to be nice. I thought to myself.

I wonder what her roommate thinks. Probably not the first time she's heard that.

I also, at some point, face fucked her with her head hanging off the edge of the bed and she was all in. And so was I. No gag, no nothing. Just stick it all the way in and let it go. And she looked prettier with a cock down her throat.

She doesn't do anal which I thought was a shame since she has such a great behind. Unfortunately, her tiny, winking asshole looked to me to be a pleasure palace. Not sure I can get the head past that air tight sphincter though, I imagined upon initial inspection. I discovered the "no anal" limitation the hard way when I slipped a finger all the way in, well past her pulsating starfish while I was banging her firmly from behind the first time.

"Not my ass! Not my ass!" Jen screamed.

"Sorry! My mistake!" I said, not really meaning it.

Oops!

With my balls slapping her clit, I unloaded and collapsed on top of her in a sweaty heap. It was a good fuck, especially after not having had it for so long. We kissed and made out like kids afterwards, and I couldn't help but start to like her. She knew I needed it and she thought enough of me to accommodate. She was fun, funny and liked to fuck. And that's what you get with older women.

Given the results of our raunchy first encounter, a few weeks later I asked her to Uber up to my place for more of a formal meeting. And yes, I figured she was broke, or close to it, so I left her some money upon my exit that first time. She didn't ask and I didn't tell her. I just left it. While I wondered how it would be received, I liked her and I didn't want her to be broke. To me, it wasn't money for sex, it was money to help somebody. And I remember the scent of her pussy flowing around inside my helmet as I rode home that day.

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She arrived wearing a stretchy black one piece, carrying flowers, of all things. A nice touch. She kissed me and said "thank you" as I squeezed her butt. That was nice of her to remember, I thought. She looked great and, apparently, she has a good heart, too. I realized at that point I was starting to like her more than I wanted to. I could feel it. Not really part of the plan.

So, we had a drink and a "Hi, how ya doin?" chat. It came out during our pre-sex convo that she not only loves to fuck, but she also loves gangbangs. Five or six guys at a time. Apparently, she's in some kind of demand for it and gets paid for each encounter. Wow. Who knew? I thought, but it made sense. She then asked me what I like, but at that point I didn't think she knew I had the dungeon. Or maybe I forgot I told her.

"I like to tie girls up and fuck them." I responded rather emotionlessly. I could see her perk up.

"I've done some bondage shoots, so maybe you can tie me up tonight?", she asked eagerly.

This is just getting better, I thought.

"OK, maybe. But I won't tie you up so you cannot escape. I don't want to scare the shit out of you," I said, again leaving her an out.

"No, you can if you want. I like it. I bet you forgot you told me about your play space! You know, your 'wife' thing. Remember?" She said.

Got me. I thought. I guess I forgot.

"Can I use you for your dungeon?" She joked, adding: "And I do love to be paddled."

"I'm almost sorry I told you!" I said, joking back. "Well, maybe I'll tie you up next time. You still don't know me." I explained. This time, I was trying to give myself the out.

The other issue was that I didn't have a plan for the night, but I kept the idea in mind. I also know bondage sex gets better as people become more comfortable with each other. Nevertheless, I did tie her up that night. And I fucked her good. Again.

I also again gave her money, which slowly began to work against me. It became a major tactical error on my part in the game we call love.

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Four years later......

Jen and I continued to date over the ensuing four years, but it wasn't really dating as I might define it. Generally, it was meeting to fuck. Or to tie her up and fuck. Yes, we did go "out", but it was with the idea that when we got together, it was to fuck. As usual, she seemed always to be between money, working at some of the crappiest jobs you could imagine. Sometimes, she would disappear for days or weeks, but I never pried as to what she was up to. I liked her and cared for her safety, but I felt it was her life and she could do what she wanted. I surmised she was probably gangbanging or dating, but I never really knew and nor did I ask. And she didn't say. At the end of the day, I felt it was none of my business.

When we did see each other however, I continued to give her money. I liked helping her; it was ok with me. But this eventually created problems. I think she liked the sex, but I'm sure she liked the money. The ultimate question, a question one would never be able to really answer here, is which did she like more? My money was on the money.

The problem with money giving in a relationship such as this is that, in the recipient's mind, it gradually transitions from being a gratuity to an expectation. In other words, you can't "un-pay" somebody and think they're not going to notice, especially now that the history of money giving for each encounter had been set. It seemed I was rapidly approaching, or already involved in, a hooker/client relationship with this woman. It was a corner I was already through, and one I had unwittingly taken. At speed.

Evidence of this was tenuous at best, and therefore could be interpreted a couple of different ways. Early on, she always tried to make me come two or three times and I was more than happy to reciprocate. She was such a good partner that, more often than not, I could come more than once during our encounters, even at my age. As the relationship progressed over time however, it sometimes seemed she showed up simply to get the cookie. She'd often get up to leave after the first round, citing some schedule excuse or physical issue.

I initially chalked this up to her age, fluctuating sex drives, or whatever, but an unpredictable pattern seemed to be forming here. Sometimes she'd fuck the shit out of me and others, she couldn't be bothered. Was this "woman stuff", boredom, a problem I didn't know about or was she treating me as a hooker would? Again, the money didn't help me answer the question. Just the opposite; I felt it was part of the problem, and I couldn't put the monster back in its box.

While working on my bikes one day, it dawned me that I had find a way to press the "reset" button here. I didn't want to marry her at my age, which probably would not have done any good anyway, and we couldn't go back to the way things were and attempt to recreate the newness we had when we first met. Similarly, talking about it would only create bad feelings and make it all worse. The conclusion I came to is she is now treating me as a paying client, or so it seemed, and the service I'm getting from Jen the hooker has been at times less than acceptable. We couldn't go on like this.

Being a Type A male, I surmised Jen needed a little attitude adjustment if she wants to continue to be my go-to hooker girl. And the bondage room was the perfect instrument for that.

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They say you're not supposed to mix real life facts and circumstances in "bondage for play" encounters. The reasoning here is it may become too personal and perhaps emotionally damaging to mix fantasy with a person's failings or inclinations. But a role play itself is oftentimes based on, or has elements of actual inclinations or desires. For example, please don't dress me up in diapers but, by all means, fuck me on one of my motorcycles. Or spank me for getting the valve adjustment wrong on the BMW. Fine with me! You bitch.

In this case, I'm now making a financial decision boiling down to who can fuck me the best for the money. Up to that point it had been Jen, but she needed to know her performance had been flagging and she therefore ran the risk of me finding somebody else, whether I actually could or not. I figured I could communicate this message in a semi-fake, playful manner, under the guise of a bondage sex encounter. I didn't want to lose her, but I nevertheless had to get the point across and answer some questions. Like: "What was the real reason she was seeing me?"

One thing about bondage is that it pays to have a plan. A plan with objectives. Sure, you have to be able to react to situations as they arise, but you need the plan first. I now had the plan. Soon thereafter, I invited my skinny, redheaded fucktoy hooker up for a play date, to which she agreed. I guess she needed the money.

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Jenny arrived wearing jeans and a T-shirt, a far cry from the flower bearing redhead in the stretchy, little black dress and heels four years ago. To set the playing field, I greeted her in a sport jacket and tie, with decent pants and shoes.

"Wow, don't we look nice!" Jen complimented

"Well, I wanted to look nice for my girl," I replied. She went to the bathroom to freshen up. Upon her exit, I ambushed her with a pair of those cheap handcuffs, the kind that doesn't need a key to get out of. With her hands behind her back, I took off my tie and knotted it around her neck. I shuffled her downstairs to the basement and the dimly lit dungeon room, steadying her with one hand grabbing her jeans and the other holding the neck tie. And I didn't do all this nicely.

"You're not wasting any time today, are you?" Jen said with a nervous laugh as I pushed her along into the room.

"No, I'm not. And shut the fuck up." I ordered.

"Ha, ha. Ok!" She said, laughing.

"Didn't I just tell you to shut the fuck up?" I asked in a mean tone.

"Ah, yeah." Jen said, realizing now I wasn't fucking around.

"Then why are you still fucking talking?" I said. Not waiting for her to respond, I ball gagged her tightly. Normally, when I used it on her previously, I left it kind of loose, but not this time.

"I really don't want the sound track today, honey." I explained. I removed my tie from around her neck, and slipped a burlap hood over her head, tightening it just under her chin. She mumbled something I couldn't make out.

During this process, I remember beginning to get a little angry with her. Perhaps it was pent up from my assumption behind her past treatment of me, but it was difficult for me to discern between real and fake. This mindset told me I had to be careful. I didn't want to hurt her or be mad at her since I had grown to like her, and she was now vulnerable, at my whims and under my thumb. Then again, she needed to get the message.

I had moved a set of wooden stocks into the room and I had had her in them before. Of all the things we experimented with, she liked that the least. I like them since they don't involve rope, which can be laboriously slow, and the stocks are more secure, albeit a bit uncomfortable. Perfect. I shuffled her over, uncuffed her, bent her over and slipped her in. In a matter of seconds, she was completely immobilized. She didn't resist.

"Ah, ee-ee ate ese ings" I could just about make out what she said.

"I know you do, which is why you are in them. And I told you to shut up."

Since there was no way to take it off, I pulled up her T-shirt and pinched a nipple while undoing her jeans, pulling them completely off. I once again marveled at her beautiful butt. I gave it a barehanded smack and a lick of her asshole. She jumped.

"Ott I asshhh" she mumbled.

"Fuck you," I said. "I'll do what I want." She didn't respond. I licked it again to make a point and she jumped a second time.

Time for the interview. I remember using a couple of lines from a favorite movie of mine at this point -- Die Hard.

"I have some questions for you, honey. Some 'fill in the blank' type questions," I declared. I got right to the point.

"What's your job when we get together?" I asked, almost implying the hooker/client relationship we now seemed to have. "What are you here for?" She didn't answer.

I continued. "You're Jen, the 'fuck and suck' girl, right? Your job is to make me come and come at least twice, correct?"

"Umf" Jen garbled.

"And why is that?" I asked. I didn't let her reply. "Because you're my 'fuck and suck' girl, aren't you?"

"Essshh"

"You're here to fuck and suck. That's what you do and that's what I need you for. And you should be fucking and sucking me from the time you get here until the time you leave. Every day, all day, right?"

Jen said nothing.

"But lately, that hasn't been the case now, has it?"

"O." Jen responded quietly.