Dear Future Me

Well future me, it sure has been quite sometime since I last wrote in this diary. My therapist asked if I have been keeping up with it, to which I lied, and said I had. She try’s to keep me in touch with myself by doing these writings, but I tend to find them rather one sided.

I have had an interesting last few days and I really just wanted to keep some sort of record as to what was going on and how I felt at the time. I have a feeling that I will be reading back over these pages in some future fap sessions.

Outside of the everyday grind of being a service technician, which takes me all over the country on a minutes notice, life has been pretty interesting as of late. I told myself I was going to start making more free time for myself while out on the road. Instead of long hours on the shop floor, followed by a quick bag of fast food shit for dinner before heading to the hotel, and pretty much passing out. I was going to make some memories. That, future self was the understatement of the century.

Considering I have never really been one to go and sit down to eat at a bar or restaurant by my lonesome, this was going to be a difficult undertaking. I started off by just going and grabbing a quick beer or two at whatever watering hole caught my eye. I don’t do dive bars, so I looked for a more,me are I say upscale type of joint.

It took a while but I got used to chatting it up with the bartenders. I made the choice early on to survey the staff before deciding to stay. Male bartenders; I bolted out the door. I wanted some eye candy, something that would make talking worth while. Not saying I can’t have a good old talk about sports with the fellas. I just preferred to always enter one of these many conversations with the goal getting laid. I know that’s a lofty goal to set, but that was my aim. I wanted to land as much tail as I could from this point on. No more lonely nights on the road. For that matter no more lonely nights at all. Home or away.

I have passed the age of wanting to settle down and be in a long term relationship. Pushing 40 and not yet married, I figured I would be content being single for the duration of my time here. This doesn’t mean I don’t want interactions and random one night stands though.

After several trips out west with nothing but light humorous chit chats along the way,I started to feel like I just didn’t have any game. Either I was always flirting with married ladies or they just weren’t up for much more. I started to go back to my old ways, work,Shitty fast food and hotels. Until one august night while in Detroit for work.

I had just finished my day working at a ford plant and a few guys wanted to hit up a local bar. What the hell, I decided to tag along. I found it much easier to open up while out with this group. They were all a few years younger, shop guys. You know fuck this fuck that. Sailors mouths. Well this bar we went to in a shitty worn out and actually pretty scary part of Detroit was a diamond in the rough. It was packed to the gills and it seemed like everyone was a regular, except me of course. So I had a spot light on me as soon as I walked in.
We decided to squeeze into a small booth near the back of the bar near the galley. I had prime seating for picking out my prey for tonight. After several rounds of beer and a few shots, I spotted the one I was going to make a move on. This girl was amazing looking. From here shoulder length auburn hair that was fashionably done reminiscent of the Farrah Fawcet look in the 70’s to her emerald eyes that seemed to powered by some sort of battery,as they were just so bright. Her tits weren’t too big but full enough to have some serious fun with. Her ass closed the deal though. It could have been the shorts she was wearing, allowing the round bottoms of her ass cheeks to peak out just enough to grant a second look, but not enough to look super slutty. She was a knock out.

I was able to manage a few words with her as she was pretty busy. But everytime she went to the bar for drinks she would make sure to freeze me with those eyes. Not just a quick glance , it was more a stare.

The guys were all getting a bit tired and the night was winding down. They headed back to their suburban homes, leaving only a hand full of patrons left, myself included. I decided to try and get Tiffany to come take a break and rest her feet. She happily joined me at my now empty booth. I’m not sure if it was her perfume mixed with the smell of beer and sweat from working so hard, but I was instantly turned on as soon as she sat down with me.

We talked about the area and things to do while I was in from out of town. I asked her directly what a man had to do to get into some trouble. This seemed to intrigue her more, as she asked exactly what kind of trouble I meant. Still not being comfortable in just coming right out and being honest with my intentions, I beat around the bush. I said I was a single guy that just want to have some fun and make some memories, and that I was open to just about any experience imaginable.
Tiffany appeared to get turned on by my question as she shifted in her seat, it looked like she was trying to position herself on the booth in way that she could move ever so slightly and rub her clit on the edge of the booth. Either that or she just had too much energy and I was reading into wrong. That wouldn’t be the first time. But there was a twinkle in her emerald eyes, and she bit her lip. She mentioned that she might have a few suggestions but wanted to feel out the situation and gage my interest over a few more drinks. She was to get off at 2:00 and suggested we head back to her place in Royal Oak, a suburb outside of Detroit

Fuck yes,this is it. I hit pay dirt finally I thought. She finished up her shift and offered to drive me there as I was too intoxicated by this time to drive. I left my rental in the parking lot not giving two shits if was even there in the morning or not. On the drive to her place we talked about everything and anything, except sex. I so wanted to just pull over and fuck the shit out her, but I wanted to see where this would end up naturally. We pulled up to her home in an older neighborhood, nice little bungalow on a tree lined street. The homes were all well kept and it was very quiet even at three am. Inside I was amazed at the decor, this young twenty something girl had taste beyond her years. I felt like I walked into an art gallery. Paintings and plants and other items around the house showed a different side to Tiffany, a more refined person than just a cocktail waitress. While she poured herself some wine and grabbed me a beer I admired the art. Then as I walked trough the hall to the bathroom things started to become darker, more edgy. The hallway was full of very sexual paintings. Women in provocative positions, some nude some just very sexual. Then I found myself pissing and the whole time I was staring at a picture above the toilet of a women looking through a glory hole at a man taking a piss, wtf I thought. I surveyed the room, and too my surprise there was indeed an actual glory hole in the wall . It was even labeled as such. Nervously I made an attempt to take a peek. As I approached the hole in the wall and bent down to take a look, I was shocked to see more art. Inside the hole was a small panting of an eye, emerald green eye, just like Tiffany’s. It was even lit by a small led light . I was hoping for the real thing, but I must admit that was pretty neat to see.

Upon returning to to the living room I seen her sitting on her love seat, smiling. Knowing damn well I had seen the hole in the wall. I sat down by my drink she placed by a lounge chair across from her.

“So did you like my art work?” She asked.
Not sure what came over me but I blurted out that I was hoping it was the real thing but that I thought it was very clever. She proceed to laugh, and tell me that she was the artist of not only the bathroom art, but practically everything in the house. Tiffany went on to tell me how she went to art school and even had work in some local galleries. She invited me to come see her next show which was tomorrow night just down the street. Of course I agreed to go. Even if I didn’t get to fuck this hot piece of ass, I would at least get to enjoy the town and have some company.

While we sipped on our drinks the conversation started to take a turn in the right direction, as she was explains the inspiration behind some of her work. I of course expressed more interest in the hallway and bathroom art. She talked about how she like watching men without them knowing she was watching. This explains the long stares back at the bar. She said that she would often drift into a fantasy about the men she gazed at, prompting her to return home and paint or sculpt. She asked if I would mind being one of her subjects. As she had been suffering from an artistic block, but when she saw me she instantly had visions of new work. The look on my face must have answered her question as she just laughed and said awesome.

She asked for me to come sit closer and I joined her on the love seat. It was so hard not to rip off every article of her clothing, but I resisted. We each had a drink more over steamy sexual conversation. Finally at one point she asked if I was attracted to her. I told her I was being a good boy but that I was starting to lose the fight with my bad boy self. She leaned in and started to kiss me. Not just light get to know you kissing either. It was unbridled passion on her lips. She devoured my tongue. My cock which I had been been trying to ignore for the last two hours sprung to life and was on a mission to either tear through my jeans or seriously cause me some pain if not unleashed soon.

Tiffany seen the mass growing under my jeans and stopped kissing me. She just stared at my building cock for what seemed like eternity. She looked at me and asked to be excused, she said she wanted to put something less comfortable on. Did I hear that right? Less comfortable? Who am I to argue I said, as she left the room. It took every ounce of my soul not to release my cock from its unfair imprisonment and jack off right there on the the sofa. I actually considered that maybe that was what she wanted and that she would be watching me from a distance without me knowing. I fought off the urge and just finished my beer.

I was unprepared for what happened next. Tiffany returned, and like she said dressed in some much less comfortable than her tank top and shorts. Her attire kinda freaked me out to the point I thought about coming up with an excuse to leave, but I quickly killed that idea. She was wearing an all black latex cat suit, you know like Ann Hathaway wore in Bat Man, but much tighter. I could see every detail of her body. It was almost like she painted it on. Her tits looked as if they were trying to escape , using their nipples to burst through at any moment. They were rock hard and looked about a half inch in size. I was speechless.
“Do you like what you see?” She inquired. No need to answer I thought and I sat there mesmerized by what was in front of me. This little girl has quite the dark side.

As my eyes made their way down her body I couldn’t help but stare and quite possible drool while looking at the beautiful form of her latex covered pussy. I could make out two small rings on each side of her crotch. She was obviously pierced down there, and I wanted a closer look. As I stood up to make a run at her, I was meet with a sharp sting from a riding crop. This just got real.
“Not so fast you horny little fuck ” she scolded. “Youre in my home and I make the rules around here”
I quickly sat down and awaited my orders. This is a first for me, I have never been in a situation quite like this. Not knowing how to react or what to say I just sat there in awe.

Tiffany began strutting around the room, her spiked boots clicking on the hard wood floor and she paced back and forth just staring at me as she slapped her hands with the crop. Looking as if she was contemplating what to do next. She then pulled at a rope that was mounted to the ceiling, what was cleverly disguised as what appeared to be a root of a tree coming through the ceiling, was actually used to pull down an apparatus from it’s hiding place above. It was an impressive design. Someone went through great trouble not only to make this, but to also be able to store it in such a unique way. From what I could gather this was some sort of device that would be used to restrain a VICTIM. It was something out of the movie saw. Straps and chains hung in place waiting for the lucky individual to be secured . She motioned to be to come closer. When I got close enough she again prodded me with the crop. It sting wasn’t as bad as the first time, it almost felt good.
“Not a word out of your fucking mouth, or you will be punished” she proclaimed.
Oh my god , I’m going to be dominated . Never being punished before I was a bit unsure of what was going to happen next. But I was soon be strapped into this torturous device I would call it. My arms were tied first above my head and together. Then she place cuffs around my feet. From the closet near by she grabbed a few rods and what looked like a collar, and began attaching them. When she finished I was securely held in place, unable to move the slightest bit. What started out as loose assortment of straps and chains , turned into a ridged device that with a pull of the rope elevated me off the ground.

I was suspended about a foot off the ground, with slight pressure on my arms and neck. But nothing unbearable. There was just no escaping. My cock had not yet seen the light of day and was starting to leak some precum. Still clothed and aching to be naked I asked her what she planned to do. With out words she pull a huge survival knife from her desk drawer and slowly approached her prey. She teased me, tracing the knife along my face, then down the front of my shirt. Moving along my waist line , down the back side of my jeans. She worked her way back up front to my swollen member. Then she applied pressure as she out lined my dick with the knife, slowly cutting the fibers in my jeans. She then moved back to my face and with just enough pressure to draw blood, she sliced into my left cheek. I know it wasn’t deep , as it felt like cutting myself shaving , but I was getting so turned on I wasn’t concerned at all.

She showed me the tip of the knife with blood running down the sharp blade. With one quick flick of her younger she licked the blood clean off, letting out the slightest moan. She than began to cut off all the buttons on the front of my shirt, exposing the first sign of my flesh . The cool air hit the sweat on my chest and sent chills down my spine. Again she went to slowly running the knife over my toned chest and abs. As I waited in anticipation she finally reach my cock again this time she actually cut right thought the material of my jeans. Removing the front portion of my pants with the precision of a surgeon, Then with one swift motion she ran the blade up through the seam of my boxers all the way to the waist band, rendering them useless . My cock was now free in all it’s glory. Away went the knife. As I took a huge breath knowing she wasn’t going to Lorraine Bobbit my member.

With my hardon standing at attention, Tiffany stared almost as if she were in a trance at my 8 inch dick. With every beat of my heart , my cock throbbed in unison. Leaking a constant stream of lube. Without saying a word she left the room and returned again with more tools. This time she had a bowl and some powder and some brushes. She began applying what I later was to discover, plaster of Paris. This chick was making a cock mold. As the heat from the plaster worked its way into my cock I asked her what she was doing. She explained to me that this was her next work of art. And that it was going to also be a useable piece once finished. I couldn’t take it . I wanted to explode right then and there. Just the visuals that were filling my head alone were enough but the fact the girl was so close to my cock but not really doing anything but painting it was driving me crazy.

Realizing I may not stay erect the whole setting up time she decided to put on a show for me. She removed the latex suit to expose her sexy body. She sat on the love seat and making sure to give me a good view of her cleanly shaven cunt. She began pulling the piercings opening her hole for me to lust after. Never once did she penetrate herself, she just violently pulled on her nipples and slapped her mound with her riding crop. She must really like putting me through this as she did her best to not reach orgasm, prolonging the agony.

Finally the plaster had set. She gently removed the mold from my cock and set it aside. She said I had been a very patient subject and now it’s my turn to be rewarded. The moment was here. I will finally be able to explode. She bent down and grabbed my cock with both hands and began to quickly stroke the whole length, I was on fire. I have beaten this thing off pretty hard before in the past but she was going to town. I thought she was trying to rip it right off. Soon she lowered her mouth on to my cock and chocked it all the way down until her nose was buried. Gagging on the thick 8inch cock she just devoured she began to drool causing her to increase the speed of her sucking. I could tell I wasn’t going to last very long as my cock started to throb more rapidly. She noticed I was getting close and stopped. She told me I was not allowed to cum yet. She quickly undid some of the straps allowing her access to remove what was remaining from my pants , dropping them on to my still bound feet.
Tiffany than grabbed some lube and started to apply it generously to my cock and aching balls. I think that if I had drank any less tonight I would have already cum. Most likely the moment she first touch my dick with the plaster. As she started to jack me off hard again I felt the rumbling deep in my balls. Feeling I couldn’t take any more she quickly swallowed my cock whole again and with one quick motion she surprised me my inserting one of her fingers right up my ass. With that I blew the biggest load of my life down this girls throat, rope after rope flew with great force into her mouth. Not letting a drop escape , she sucked my dick dry.

I have never had anything near my ass in my life, but I can tell you know, it will not be the last. That was the most powerful load I ever shot. I will be doing some poking around back there on my own to see just what it’s all about.

Tiffany whipped her mouth off on her arm and with an evil grin said, ” I think you will be calling off work tomorrow, so why don’t you just hang around and we will play some more in the morning,” then she turned around shut the light off and went off to bed, leaving me there suspended in her front room.

Helpless, I accepted my fate. Wondering what tomorrow would bring,

Until next time my future self.