I was in Southern California when this happened. I was on a vacation with no particular plan in mind, except to just get away from it all. I was riding my longboard down a long and deserted neighborhood street when this all began. As I rode my board, I would constantly look behind me to make sure that there were no cars coming my direction as my back was to the road. For about 10 minutes, it was just me on the road, and then when I looked back, I saw a black car approaching me so I moved to the side of the road to let them pass.
Judging by the distance, I figured they would pass in about 2 minutes. After about 5 minutes the car had still not passed me so I looked behind me to see that they were pacing me.
The car was just far enough away to that it wouldn't hit me, but enough to know that they were following me, so I stopped. When I stopped the car moved up to make me even with the back window, and they rolled down the window.
When the window rolled down I bent down to see who I was going to be speaking with and I was met with two of the largest breasts that I had ever laid my eyes on. I stared for a moment, then I came to my senses and looked up and locked eyes with the gorgeous brown eyes of Denise Milani. She smiled at me and said,
"Do you need a ride somewhere?"
I stared at her and stumbled around my words, mumbling, "Um...er....yeah...."
She continued to smile and said, "Then get in. I will take you there."
So I got into the car, and as we drove off, Denise said, "Do you mind if we make a quick stop before I drop you off?"
I shook my head indicating that a stop would not be an issue, she smiled and continued,"My name is Denise, what is your name?"
"My name is Rusty." I mumbled
.She smiled and said, "Nice to meet you Rusty, do you know who I am?"
I went red, in my head I thought, *of course I know who you are! You have been my go-to girl since the mid-2000s! I have jacked off to you daily for years! I have dreamed of fucking you for years!* and what I said was, "Yeah, I know who you are, aren't you an internet model?"
She smiled and said, "Yes, I am, I loved doing that, but now I do more fitness, but I loved being a model. How did you find out about me?"
*Fuck, what is with all these questions? Think fast...be polite and not too vulgar....*
"Um, honestly I was searching on the internet for gorgeous women with an ample chest and I came across your pictures and I loved them instantly."
Denise smiled, "You can tell me the truth, what did you do with that picture?"
I felt a little more at ease, "I jacked off to it, that's when I was hooked. Honestly, I came to that picture 3 times that day! I have cum to you each day since then at least once!"
She smiled and said, "Good, I'm glad to have been of service to you all these years! That was always my goal, to make people smile and cum. Hearing that makes me happy. So thank you for sharing that with me."
I was beet red, "I... uh.... yeah.... you're welcome."
We chatted for a few minutes and then the car stopped. She said, "Please get out, this is our stop."
I got out of the car and we were in front of a house, and Denise motioned for me to follow her up to the house.I followed her and she led me into a gorgeous house, it was a very large house, with beautiful furniture and decorations. Denise led me to a room with a couch and some chairs and a large TV. She told me to sit down and she said that she would bring something to drink and to eat.When she returned she sat down on the couch next to me, her voluptuous breasts bouncing as she sat. I tried my best not to stare as her deep cleavage was bared to me as she bent over to pass me a drink.
She smiled at me and said, "Rusty, it is very nice to meet you and I'm glad that I could meet such a fan like you. I have a proposition for you, if you choose to accept. Would you like to hear it?"
I swallowed hard, *What could she be possibly thinking* "Sure, I would love to hear it."
She smiled and said, "I have always wanted to do this with a huge fan, but I have never met a fan worthy of this challenge, until you. The challenge is this; I have every video that I have ever done when I was doing my modeling and I will choose one video for you to watch and you are going to jack off to that video. But, you cannot cum. If you cum, then you lose. The video will be at least 5 minutes long, if not longer. If you don't cum until the end of the video or at all, you win. If you don't cum, I will finish you off. You can cum when the credits begin, but if you cum before that, then you lose. You have to be jacking off the entire time, you cannot stop. I have lube and lotion for you to use and I will provide a towel for you to either wipe yourself if your cock gets too slippery, or if you cum. The only time you can stop is to wipe yourself if your cock is too slippery to keep going. If you stop, you're done and you lose, you cannot even finish. I will be egging you on the entire time, I can get right up in your face, but I cannot touch you. You cannot touch me, if you touch me, you're done, and you can't cum. If I touch you, I will immediately suck you off. Your goal is to not cum at all, because if you don't, you win and then you get to pick 3 things that you can do to me. I will fuck you if you win and you can pick 3 thing that we will for sure do. For example, if you have always dreamed of titty-fucking me until you cum and then you cum on my tits , we can do that as one of your 3 things. If I offer something, it doesn't count as one of your 3 things, even if that's something you want. I choose how long we will fuck, and it will be at least 1 day, if not longer. Also, if you win, then you reserve the right to ask me once more for a period of fucking at your time of choosing. After that, you must complete the challenge again in order to fuck me. If I invite you to fuck me, then you won't have to do the challenge. Is that clear? Are there any questions?"
"Actually I do have one question. Can I try again if I lose?" I asked.
"Not today, but if I invite you to try again, then yes you may." She said with a smile. "Anything else?"
"I don't think so... let's get started." I said.
"Remove your pants." Denise said, "I'm going to pick the video."
I removed my pants, and Denise turned on the TV and began searching through her video files, and I impatiently waited for her to pick the video. I was going through my head what videos of hers were longer than 5 minutes and if I could last throughout the entire video. As I was thinking, I knew there were a couple that I could probably last the entire time, which of course was my goal, I wanted to fuck her, and I wanted to fuck her hard.... That would be a very difficult task given the fact that Denise was right in front of me and I would be watching a video of her... I wasn't 100% sure I could do it, but I would make sure that this was the best fap of my life.
Denise found the video and queued it up and then left the room to get the lube and towel. Moments later she returned and she bent over me, revealing her deep cleavage causing my cock to begin to grow. She said in a sexy whisper, "Are you ready?"
My cock was fully erect when she said that. I couldn't speak, so I nodded. She stared into my eyes for a moment and then turned away, causing her massive breasts to jiggle, causing my cock to throb with delight. Denise pressed play on the video, revealing a video that I was familiar with, as I had cum to it many, many times. It was an older video of hers, it was labeled, "Just For You" clocking in at just about 7 minutes. Once Denise appeared on the screen, she said, "Begin to stroke. Do not stop or you are done."
I began to stroke, I didn't add any lube yet, just to get the groove going, I started fairly slow, and she didn't tell me that I failed so I continued at a decent pace so that I was still feeling good, but not enough to cum.
I knew the video well, so I hoped to use that to my advantage.
As I stroked, Denise began to dance a little to the music, she slowly began to take off her shirt... I stared, her bra was a pretty black lace bra, and had a very deep plunge in it to perfect her goddess-like cleavage. I felt my cock throbbing in my slowly stroking hand, and without realizing it, I sped up my stroking. Once I realized that I was feeling a little too good, I began to slow my stroking and continued to watch the video.... I looked at the timestamp and realized that I had about 4 and a half minutes to go... I could do this... I hoped.
Denise began to play with her bra and adjust her tits and then she said, "Add some lube, you don't want to chafe." So I obediently added some lube and continued to stroke with ease. Denise stepped a little bit closer to me and she bent over me, close enough to touch me, but not touching me at all... my hand instinctively went to grab her massive breast, but I stopped myself, promising to grab it later if I won.
She said, "Watch the video, don't lose focus, don't cum." I almost came when told me not to. I watched the video and continued to stroke, and Denise began to egg me on, "Don't cum, keep stroking, you know you want it! Faster! Stroke like you mean it!"
I obediently followed her instructions, I had about 2 minutes to go at this time. I could feel my cock throbbing, I wanted to cum so very badly, I could feel the precum sliding down my cock in ribbons. I didn't know if I could make it... there was only one minute to go... Denise yelled, "Stroke it Rusty, Stroke it faster!"
I was vigorously stroking my this time and I was feeling almost too good, I almost came, but I got a second wind when I saw the time, 30 seconds to go... I kept stroking, my cock was throbbing, 20 seconds.... Denise put her face so close to mine and said, "You can cum now." and winked. I didn't cum, 10 seconds.... still stroking, 5 seconds.... still stroking, my cock hurt from the sexual tension and the video finished and I hadn't cum.
Denise stood above me for a moment, staring at my cock, which was throbbing immensely, and she didn't see any cum. She looked me in the eyes and said, "You did it. You won." She looked down at my cock again, and then said,
"I guess I need to finish you off...." She smiled at me and knelt down in between my legs.
She began to rub her hands across my legs, and then she took my cock in her and began to slowly stroke. I couldn't believe it, Denise Milani was giving me a handjob! I wanted to enjoy this moment, so I did, and Denise added a little more lube and then she brought her massive tits up near my cock and put my cock in between them and began to tit-fuck my cock... I knew that I was going to cum, Denise could see it in my eyes, and then with one final stroke between her massive, perfect tits, I came, I came all over those tits and even a little got on her lip. 4 creamy loads of hot, steamy cum shot all over Denise's perfect tits and a gob landed on her lip, which she licked off and swallowed.
She stood up, grabbed the towel and wiped herself off. She looked at me and said, "You won. How was that for a good jack off?"
I smiled and said, "It was the best fap that I have ever had!"
She smiled and said, "Come up to my bedroom, we have so much more to discuss, such as your 3 things that you wish to do with me."
As I followed her up to her room, thoughts filled my head of what I wanted to do to her....
