My wife had gone out of town to visit her mother for the week. It was summer so our usual babysitter, Jennifer, was home from college and could watch them until I got home. We had used her for many years and I had watched your grow up. Now that she has turned 18 she was become totally hot.
She was very tall, 6'1" and thin. Her ass was beautifully shaped and her tits had grown to what I would guess to be a sexy D cup. Regardless of her cup size, her tits her huge and beautiful. They were perfectly shaped and defied gravity.
Her hair was long and straight. Its color was the same as her eyes, brown; eyes that you could look into all night long. Needless to say I was counting the days until she turned 18. Why I did this I have no rational clue. As if when she was legal she would throw herself at me and beg me to take her.
When she finally reached that magical age of consent I would surreptitiously take pictures of her in her tight sexy clothes. The pictures centered mostly on her tits and ass. One day she came over with her hair up in pigtails. It looked very hot and innocent. I took lots of pictures of those pigtails.
Occasionally, I would take legitimate pictures of her to explain why I had a camera out and was snapping pictures. I would then download them onto my computer so I could leer at her sexy body. This went on for the two months leading up to my wife's week long getaway.
A couple of days before my wife was scheduled to left she asked Jennifer to come over to the house to go over instructions and the regular weekly routine. When Jennifer stepped into the house my mouth fell open as I gazed at her, oblivious to any and every thing else. She was wearing one of my fantasy outfits. It was a thin cotton tank top / wife beater that was at least two sizes too small. It came down above her belly button and the material strained against her tits. She was wearing no bra and you could see the outline of her areola. Her movements made the material of her tank top rub against her tits. Her nipples were starting to show the early signs of hardening.
In addition to her tank top she was wearing a pair of cut off jeans. They, too, were very ill fitting, thank God. She had cut them off unbelievably short. From the front they snuggly pressed against her young pussy. You could see the lips of her pussy on either side of the seam. She flashed me her sweet little smile as she passed. I told the ladies I had some work to do in the back of the house; run get my camera, and excused myself.
As I walked down the hallway I heard a set of keys fall to the floor. I turned toward the noise in time to see Jennifer bend over to pick them. Her shorts showed just a little bit of her beautiful ass. But when she bent down her shorts exposed more and more of her glorious ass. I wanted to run to her, throw her to the ground and fuck her brains out right there in front of my wife.
I hurried back and retrieved my camera, quickly reappearing in the den. I took a seat in my chair. I was waiting for an opportunity to snap a picture of her. I knew it would be impossible but more than that it was stupidly dangerous. There is no way I could take a picture of her in that outfit without being caught. At the very least, someone would spot the camera.
I sat there for what seemed like an eternity. My heart was pounding in my chest. I don't know how they couldn't hear it. I felt like I was noticeably sweating. This was stupid, I would never get a picture but I held out all hope.
Over and over again I wanted to take her picture but I couldn't get the shot. She would stand up, bend over or stretch. Each movement would accentuate a part of her body; legs, ass, tits, pussy. I was going crazy. My dick was as hard as a telephone pole and it felt as big.
Then just as I was about to give up hope my wife went into the kitchen. Jennifer followed her and stopped in the doorway. They where there talking for awhile, going over things in the kitchen when Jennifer bent over. This was it. I had a perfect shot of her ass and I jumped at the chance.
Jennifer straightens up and my wife's hand appeared from inside the kitchen with a key to our house. Jennifer took it and walked over to her purse. She leaned forward. As she did her tits were pulled toward the floor. I got another picture of the top of her tits and her incredible cleavage.
I quickly jumped up, wanting to get out of there before I was caught with the camera. I hurried back to my bedroom and downloaded the pictures into my files of her. I spent the next two days reliving that experience. I would get hornier and hornier thinking about them. I wanted to look at the pictures but my wife was always around. I was going crazy with anticipation.
My wife finally left Sunday. I spent all night Sunday looking at her pictures. Most of the time I was looking at her pigtail photos and that outfit she had wore just days before. I couldn't take it any longer. I printed out three pictures. One of her beautiful face, smiling with those pigtails. One of her ass in the cut off shorts. The last one was of her tits in the tank top.
That night I looked at those pictures in bed and jerked off all over them. It was an incredible load. I was so horny from looking at those pictures that I shot three thick streams of cum. Feeling very satisfied, I rolled over and fell into a deep restful sleep.
I woke the next morning to the sounds of Jennifer coming in the house. I hadn't set the alarm nor had I cleaned up from the night before. I quickly put her pictures in the night side stand where we keep our toys and pulled on some pajama bottoms. My dick was hard from the usually morning hard on. I stuck my head out of the bedroom and explained I had over slept. I turned to get ready for work, hoping she wouldn't see my dick but she seemed to linger in the hallway just a little longer than usual.
As I left the house she flashed me her sweet smile. All day long I was thinking about Jennifer and how I would love to feel her lips wrapped around my dick, rub my dick over her ass and bury it deep in her sweet pussy. I left work early wanting to get home fast to see her.
When I got there her mood was even sweater and more flirty. This seemed a little odd but I loved the attention.
That night I crawled into bed and pulled out the cum stained pictures of Jennifer along with our bottle of lube. I slowly stroked and teased my dick while I gazed at the pictures imagining what I would like to do to her until I shot another huge load all over her images. This time I put the pictures away and set the alarm.
This went on day after day. The same routine of a glimpse of her in the morning followed by constant thought of her all day long. Then returning home horny to ogle her for the time I had left. Again, she seemed a little more flirty and forward, almost to the point of being horny.
At night I would pull her pictures out and jerk my dick until every drop of cum was drained from my dick all over her face, tits, ass and pussy.
Friday finally had come. I wasn't looking forward to Jennifer leaving. I had enjoyed the company of a young beautiful woman that made my dick hard every time I saw her.
I was about finished getting ready for work when Jennifer showed up. Speechless doesn't begin to describe my reaction when I saw her. She had her long beautiful brown hair in pigtails. She was wearing the same thin white tank top and tight cut off jeans she had on a week earlier.
I just stood there staring at her, not saying a word. She snapped me out of my trance by asking me if there was something wrong. I replied that everything was fine.
Jennifer asked again "are you sure nothing's wrong?"
"You just were standing there looking at me."
"What's wrong," she continued, "don't you like my outfit?"
Knowing I had been busted I tried to play it off as nothing special. "No, no everything's fine." Everything was fine except my dick was about to rip my pants. "You look just fine."
She started to explain why she was dressed like that. "I was going to wash my car today and this is my car washing clothes." Ok so now I know she is going to get her tank top soaking wet and her nipples would be hard and she would be showing everything.
This was more than I could take. I had to go back to my bedroom and stroke my dick for some relief. I knew I couldn't make it through the day without getting rid of this load she just made. I got to my room and pulled my dick out and started stroking it.
I was just about to cum when I heard Jennifer clear her throat. I looked up and saw her in the reflection of the dressing mirror that was in my room. She had been standing there the whole time watching me jerk off. I quickly put my dick back in my pants only to have some cum leak out of my dick and into my pants. She was staring me right in the eye. She giggled, turned around and walked away down the hall.
There wasn't time to change clothes so I had to go to work with cum in my underwear. I started toward the door. When I met Jennifer in the kitchen she was eating a banana. She turned to wish me a nice day at work. But as she said this she looked me straight in the eye and I swear she caressed her tit. She then looked right at my dick and started to laugh tauntingly.
She knew she was getting to me. She knew I was jacking off to her and she loved every minute of it. I hoped I was imagining it so I asked her what she was laughing about. As I asked her she slid the banana in her mouth like she was sucking cock. She slowly pulled it out of her mouth and said "oh nothing really."
"I was just thinking of a little something that happened a while ago."
"Do you want some?" she asked as she gestured toward me with the banana.
"No thank you," I said. "Really, what were you laughing about?"
"Oh, I was just thinking about an old boyfriend." She slid the cock-like banana back into her mouth and out again. This made my dick ache even more. "He would do anything I wanted." One time I even got him to ......" She stopped there. "Don't you need to get to work?" She then teasingly laughed again and told me she "hoped my day wouldn't be too hard."
But the day was very hard, because of my dick. The phone rang in my office. I picked up the receiver and heard a sucking sound on the other end of the line followed by a pop. "Hello?' I said. "Oh, hi."
"I didn't realize you had answered."
"What was that noise, Jennifer?"
"Oh, I was just sucking on a popsicle."
"I wish you were here, you'd love it." She slid the Popsicle back into her mouth and moan softly. "Why are you calling Jennifer," I asked?
"Well, you seemed uptight when you left this morning."
"I just wanted to check and make sure everything was ok with you." I assured her I was fine and there was nothing to worry about. She continued to noisily suck her Popsicle. I could imagine what it looked like and how it would feel if it were my dick instead of the Popsicle.
"That's good," she said. "I wouldn't want you to have to pull your little dick out at the office and stroke it without me." She laughed teasingly and hung up the phone before I could say anything.
I started to melt. My dick got even harder than before the call, if that was possible. Then a wave of embarrassment washed over me. She said it out loud. I knew that she saw me this morning but I was in denial, hoping it wasn't so. But she slapped me right in the face with it. Not only did she see my stroking my dick but she also saw how little my dick was and she was mocking me.
Somehow this humiliation made me even more excited. My nuts were full of cum and I needed a release quick. My hand involuntarily found its way around my dick and I began unconsciously stroking my dick through my pants. I was too far gone. I couldn't make it without emptying this load of cum right now.
I got up and went to the bathroom but both stalls were full and someone was at the urinal. Not that I would jerk off in the urinal but I was so horny I didn't know what I was capable of doing. I washed my hands and left.
I felt like every woman I passed by noticed I had a hard on; every smile was really a stifled laugh. I made it back to my office. I clicked on the waiting e-mail. It was from my home address. The subject line was "Bad Boy"
Jennifer had written "I found these naughty pictures on your computer."
"What would your little wifey say if she knew about these?"
"Would she understand or would she be very very angry?"
"I have one other question for you."
"Does this make your little dick hard?"
"I bet it does." I opened the attachment. She attached the picture of her bending over in the cut off shorts. I was so humiliated but my dick was so hard.
A few minutes later I receive another e-mail. "I haven't heard from you."
"Is something wrong?"
"Maybe you didn't like the picture I sent you."
"Since you seem to like what I'm wearing today I hope you'll like this one better."
"Hehehehe!" I was almost afraid to open the attachment. But I knew it had to be the picture of her bending over showing her tits.
I opened the attachment and it wasn't what I was expecting. She had taken a picture of herself. She had found my wife's toy cock. It looks just like a real cock but it is 8 inches long. She was looking directly in to the camera as if she was looking at me and she had every inch of that cock in her mouth.
The phone rang. It was Jennifer. "Did you get my picture?"
"Yes I did," I replied. She could hear the weakness of my voice. "Yeah, but did you like it?"
"I bet you want me to suck your cock just like that."
"Yes I do."
"Well then you're going to have to show me you deserve to have me......suck.... your.... Dick."
"Anything, I'll do anything." She must have liked my answer because she said "aren't you the horny little boy?"
"Yes you will do anything and everything I say if you want to feel my lips wrapped around your sweaty little dick"
"The FIRST thing I want you to do is pull your dick out and start stroking it, nice and slow."
"Don't go too fast, just barely touch it while you slowly stroke."
"I can't do that. People are around. I could get caught."
"If you want my lips around you dick, you'll do it for me, please."
I can't believe it but I started to unzip my pants. I pulled my dick out and started to slowly stroke it just like she wanted. As I began I couldn't help but let out a long soft moan. From the other end of the phone I hear Jennifer say "that's a good boy; it feels so good doesn't it?"
"Yes Jennifer, you got me so horny I've needed to stroke my dick all day long."
"Just like you did this morning?"
I was powerless. I had to admit it. "Yes" was all I could muster.
"Do you like to stroke your dick while thinking of me? Do you want to get your hands on me so badly that you just have to grab your dick and cum all over yourself?"
She was teasing me and bringing me closer to cumming. I knew she could hear it in my voice. "Yes I do."
"That's a good little stroker boy. Are you going to cum for me?"
"Yes," I said. "I'm going to cum."
"Then STOP," she said. I immediately stopped stroking my dick. I was only two or three more strokes away from relief. She could hear my moans of frustration as I stopped. "That's a good boy," she continued. "Now you hurry up and finish work so you can come home."
I finally finished the day and hurried home. There she stood waiting for me in her tank top and cut off jeans. She was slowly caressing her tits. Her hands made there way down to the seam of her jeans and she gently traced her pussy lips. "So you've been waiting for this all day long haven't you?"
"Yes, I have. Please I need release."
"Good, go to your room, take off all your clothes and lie on the bed and wait for me." I did as she instructed. I was in the bed naked for an eternity before she showed up. She seductively entered the room dangling a pair of handcuff from her finger. Without saying a word she cuffed my hands over my head and over the head board. I was totally at her mercy.
She climbed on the bed fully clothed and sat on my dick. She slowly began riding my dick. Her jeans were rubbing against my dick. It was rough and hurt a little but I didn't care. I needed to cum. She rode me until cum was leaking out of my dick. Then she climbed off and sat next to me and gently took my dick in her hand.
That's when things turned for the worst. As she stroked my dick she said "you don't think I'm going to fuck this little thing? Don't you have a man sized cock?" She started seductively laughing. "I want a real dick. Like this one" In walked one of her friends. He was naked. His dick was huge; and then another and another came in. There I was tied to the bed naked with my dick fully erect and Jennifer laughing at me.
She started stroking my dick and talked to her friends "look at this little dick and he thinks I'm going to make it cum? Well, he's very wrong about that. I want a fat dick." With that she grabbed a dick and guided it in to her mouth. By the moans she made she thoroughly enjoyed it. She was almost whimpering on his dick.
"You promised me you would let me cum if I did want you wanted." She slid his dick out of her mouth, turned and looked at me and said "you're right. If you do everything I say you will get to cum. But I found these pictures in your night stand. Is this what you think of me? Is this what you want to do to me? I found these Monday and there was a little stain. Then on Tuesday there was more. Every day more and more of your cum appeared on my face, chest and ass. How do you explain that?"
I told her that she was so sexy that everyday she made me cum. I couldn't help from stroking my cock when I saw those wonderful pictures; thinking of her sucking my dick until it exploded. "Well if you love cocksucking so much then I'll make your dreams come true."
With that she took the cock she had been sucking and led it to MY mouth. "Here is your first job. Suck all these dicks starting with this one. Do it or you won't cum." I started to open my mouth. As I did she started laughing out loud. "Look he's going to do it. He's going to be a little cocksucker." He pushed his cock into my mouth. Jennifer was still stroking my cock and now I had another man's dick in my mouth. I was so horny I didn't know what I was doing or thinking.
"Oh look at him. What a good little cocksucker his. You love sucking big dicks, don't you?" I don't know why I said it but I said "I do. I love to suck these big cocks." They all gathered me and I started sucking all of them in turn. I said it because it was true. I couldn't get enough cock in my mouth. The cocks I wasn't sucking I stroked. Jennifer must have been right about me being a good cocksucker because in no time they each started twitching. Then in order all 5 cocks unleashed their juicy load all over my face. Load after load. I loved it. I wanted more.
She had turned me into a cock hungry whore just for the chance for her to make me cum. As the last load of cum hit my face it felt so good as if I were cumming too. As they each cleaned their cocks on my face Jennifer stood up and started to leave the room.
I asked her where she was going. She promised me. She said "I promised you I was make you cum, and you did." I looked down and on my chest was a pool of my own cum. She made me cum alright but it was from sucking cock.
"I am going to have to have more fun with you." She bent over and scooped up a big load of cum with her finger and fed it to me. "Ooouuu he likes this. Look how his little dick got hard all over again. Are you going to be my little cumslut; my cocksucking, cum drinking slut?
She merely laughed and walked away. One of her friends threw me the keys and they all walked out. What had just happened? What had I done? I didn't know but I loved it while it was going on. I wonder what else she has in store for me.