The Longest DaybyUnomeasBob©
Ever heard the phrase "it's the quiet one's you have to watch out for."? Well, that's me. By day I am an upstanding citizen, a public figure, and neighborhood leader. Exactly the type you see in old TV shows and movies, well respected and highly admired. But at night I read erotic literature, watch porn and talk to multiple women without any knowing of the other. I play the "goodie-goodie" role so well that women trust me almost instantly. I have realized just what trust can get you, a naked woman. When I say this I am not claiming to smooth talk women, no I am claiming that they try to smooth talk me into sex even after I tell them I am not looking for a relationship. Of course I "reluctantly" engage them.
I have written several of my encounters in my journal, but my reputation won't allow me to tell my exploits to even my closest friends. So here I tell you one of my stories from the anonymity of a computer screen. Other than the names of those involved, I give my word that every other detail is the truth. My first story I have titled "The Longest Day." I hope you enjoy reading it as much as I enjoyed living it. You can call me Jason.
I don't remember the exact date but it was around 2am and my phone rang. It was the weekend and I was up watching TV. As I answered, a loud and obviously drunk female voice on the line asked for Jason. Now this particular conversation isn't that important to the story, but what matters is that the girl had a wrong number, and as luck would have it the person she was calling happened to have my name. The next day she called again and with a more sober tone apologized for her late night calling. Needless to say, she sounded cute so I continued the conversation and a couple hours later she asked if I would mind her calling me again sometime, and that is how my story started.
For about a month, we talked on the phone several times but hadn't decided to meet, until one day we started talking sexual fantasies. My entire life I have been the leader, the one in charge, the one telling everyone else what to do. It would be a dream for once to let my guard down, not be in control, be a submissive. This particular fantasy doesn't involve whips, spikes, or anything being inserted into my ass, it's simply a matter of allowing someone else to have control. This girl, Diana was up for the challenge.
She laid out the rules for our first face to face meet. I was to rent a hotel room for the day and leave a key card with the manager for her. From there I was to go to the room, which had to be ground floor and facing the pool, and prepare for the day. My guidelines were to strip naked, blindfold myself and lay face up in the middle of the bed. For that day I had only three rules, I couldn't talk, move, or cum unless I was told otherwise. I had become her sex doll for the day, and she expected my penis to be ready anytime she wanted it.
The day came and I did as I was instructed. I was laying there completely naked and blind to the world thinking of how I was about to be used as a sex toy by someone I had never met, never even seen. It was at that point I got one of the hardest erections of my life. I heard the door open and someone walk in. Without a sound, the person tied me spread eagle to the bed. A slight fear swept over me as I heard the sound of the curtains being opened to what I remembered being a clear view from the swimming pool. The voice from the phone leaned over to me and whispered, you are exposed so that anybody that happens by can see you. I will be back whenever I am ready, and I expect your dick to be just as hard then as it is now. She walked out the door.
As I lay there part of me started thinking of how anybody could walk by and see me laying there, with that thought in mind, I had no problem keeping the erection. After a brief period she came back in, closed the curtains and locked the door. She came over to the bed and straddled me with only the head of my dick going inside her. She reminded me of the rules making it clear that I was not to move or cum until she told me otherwise. She rocked back and forth keeping the tip of my prick inside of her but nothing more. It took all my will not to become a jackhammer and start pounding upwards further into her pussy.
It was then that she told me her plans for the day. She would go swimming, watch TV, read her book, and satisfy herself using my dick any time she had the urge to sit on something. She could cum, and she would cum, but I would not. She made it clear that at any moment if she wanted sex I had to be erect and ready for her to use my penis as her newest toy. If it softened or if I came I would be punished. So at 9am that morning she started.
If you ever get the chance to be a woman's play thing for the day I highly recommend it. After she had finished telling me the details she began to ride me harder than I had ever been ridden before. I was nothing more than one of her favorite toys at that point; a vibrator that she could ride as hard as she wanted, as long as she wanted, and not worry about the batteries. She was screaming aloud, I was screaming inside. Oh God was I ever screaming. My dick got harder and tighter until I felt like I was nearing the point of no return. I tried to relax breath normally and think about baseball. It was about that time I felt her body go limp briefly before she climbed off. I heard a bag of chips open and the TV come on.
All I could think about was how my nuts felt like exploding and releasing their occupants. I slowly brought myself into a relaxed state while managing to maintain my erection. I knew she was still naked, and that even though the TV was on she was more than likely still looking at my swollen and wet flagpole. 30 minutes might go by fast if your watching a good TV show, but if your laying blindfolded with the knowledge that at any minute your penis could be shoved into a mouth, or a pussy or ass for that matter, time drags on and on. I had no idea the time, but assumed it was around 11. She had rode me for what seemed like around an hour then went to watching some show.
It was around that time that she came and straddled me again, this time her pussy on my chest. She took my cock in her hands. I heard her say, I wonder just how big my new toy really is. I felt both her hands gripping my dick and almost reach the lip of the head. Now I am no monster dicked freak, but I have around 7.25 inches, of perfectly straight meat with a large mushroom on the end. Rather nice looking if I do say so myself (wouldnt mind another inch though). Well she continued to inspect her property and play with her toy using both her hands and her mouth. It didn't seem as much as a way to pleasure me, as it was a girl examining her first cock.
I could smell her pussy getting nice and moist. I could feel its warmth on my chest; my penis was trying to relieve me of some of my swollenness by releasing large amount of pre-cum. I could tell this girl had a slim and short body, but her breast felt huge against my stomach. She slowly slid back against my face and told me that I could have lunch. I licked at her clit a little, but my main goal was to get my tongue inside her cunt and feast. She bucked against my face and began squeezing my cock in her hand as though it was a handle to keep her from falling off the bed. It was a painful experience, but I have to admit, I really enjoyed it.
Throughout the day she continued to do similar sexual experiments, each seemingly designed to please herself and remind me that I was nothing more than a ready made dildo to her. She got on my dick and rode me more times that I could count, mainly because the time between rides was never the same. Sometimes she would make me wait for what felt like an hour, sometimes she would get off only long enough to change the channel on the TV and get back on. At one point she decided she didn't want to fuck me, but she enjoyed feeling my cock inside of her so she stayed straddled with my dick inside her while she flipped through the channels.
If a man learns to control the muscles around his cock he can make it jump or dance around. She knew that I had this talent and while she was sitting there watching tv she had instructed me to make it bounce while it was still inside her.
After a couple times of her using my penis as a sexual saddle, the lubrication on the condom would wear off and need to be switched out several times during the day. She tried several different types of condoms. Everything from heated to extended pleasure. I honostly couldnt tell much of a difference.
It was unlike any experience I've ever had, laying there trying not to cum while you have a hot and moist pussy holding you tight. She hadn't talked to me since lunch, but she untied my arms and legs and said that we were going to the shower. Once in the shower I proceeded to wash her entire body while still wearing my blindfold. She then instructed me to get down on my knees and start eating her out while the water ran over her. I ate her pussy as though I was a hungry bear lapping from a bowl of honey.
We got out of the shower and without drying off walked back toward the beds. She told me to continue standing and asked me if my nuts felt as sperm filled as they looked. It was at this point the day was almost at an end. I had been fucked, sucked and stroked all day and my dick felt like it was about to explode. She got my cell phone and called my best friend Mark. She handed me the phone and instructed me to talk, not cum until she said I could, and no matter what Mark couldn't know I was getting my dick sucked dry.
It is hard to find something to talk about while a girl has your cock halfway down her throat, but as she uttered three little letters, a single word, an entire days worth of pent up energy was released into her stomach. After a day of being forbidden to cum, all it took was her saying the word "now" to make me wonder just how much sperm a body could produce and how many jolts it took to remove it all.
As I fell onto the bed, she removed my blindfold to reveal a very attractive set of breast. She was just as beautiful as I had imagined her when I first heard her over the phone. Around 5 foot 3, I would guess around 120 pounds. Dark brown hair and a light tan. She had a stud in her tounge and a bar in one nipple. A small patch of hair just above her clit that was shaved to look like a V.
Her job caused her to move 2000 miles away and I don't see her anymore, but that day was one that I will never forget.