I am a Spanish substitute teacher at a Catholic high school. On the surface, I appear to have a routine life. While I prep the teens for their life ahead while mine passes by seemingly uneventful. Hardly! Just wait till I tell you how I started pegging my sugar daddy. After all, I had fucked my stepdad when I was a young girl and I knew everything there is to a sensual pegging, so this was a walk in the park.
Being in my early twenties and living on a substitute teacher salary was very limiting. So I took the initiative to take extreme measures. And that was to find my sugar daddy that could not just enhance my lifestyle but also let me expand on my sexual interests & desires to try about anything!
Boy, did I hit a homerun with Robert? Poor Robert!
Robert was about twice my age and wealthy. A big executive that traveled a lot for business. He had a condo in my city (Miami) that he stayed at when business required him to be here. This was perfect! No wife or kids to interrupt us. Basic stuff at first – blowjobs and a lot of fucking with me doing most of the work. He liked to be in control and catered to. But change was in the air!
Eventually, I had a key to the condo so I could be there to greet him when he arrived. He always had a specific time for me to arrive. Well, one time he was already in town when he called me and told me to meet him at 8:00 PM. I decided I would surprise him and be there earlier. I knew he always was showered and waiting on me when I arrived so this time I was going to surprise him by helping him shower and get both of us squeaky clean. Well, I was the one being surprised.
I walk in a couple of hours early. No Robert. But what the hell is this “Mr. Vanilla” been jacking off to? On his computer is a porn site strictly about women pegging men! I was shocked but also very turned on! Was Robert keeping a secret from me? Pegging my sugar daddy was a gold mine! My pussy got wet and I saw dollar signs $$$!
When Mr. Big Executive walked in he was no longer in control.
Something came over me and I had never been so excited. Robert, or Bobby as I no called him, was putty in my hands. I asked why he hadn’t share this desire – fantasy with me. He told me he was embarrassed about me knowing his desires. I asked directly, “Bobby do you want me to fuck you in the ass”? He said no but I knew he was lying…
Me- “Why do you watch these videos”?
Bobby- “I don’t know. Kind of curious. Maybe interested, but nervous, maybe even scared”.
Me- “Scared it will hurt”?
Bobby- “No, scared I will like it beyond my wildest imagination”.
Me- “Have you fingered yourself or put anything in there”?
Bobby- “No”
Cha-ching!! $$$$ My ship had come in! A virgin wonderland for me to ravage! Pegging my sugar daddy was going to make me lots of money!
I wasted no time to act but knew I had to lead him along. I rush it and his little pink rosebud might run for cover. From then on I drove everything. Times, where we met, what we would do, etc. He had one duty and that was to do what he was told to do. He had never been treated this way and I knew he loved it. Even though he was whimpering like a little baby most of the time.
I started him with lube and an introduction to my middle finger. Once I got full length with my finger I would rub my face all over his cock but not let him cum. That was a key factor in our budding relationship. I controlled his orgasms! He was going to have to earn his release by obeying and impressing me. I could not wait until I started pegging my sugar daddy on a daily basis. I knew that in order to get spoiled I had to treat him right and that was the main goal.
By the next night, I had two fingers in his man pussy.
Which is what he was to refer to it as. It wasn’t long before he was canceling travel plans to be around for longer periods of time. His development was coming along nicely. He quickly got introduce to a small dildo, a glass dildo, a ribbed dildo, etc. He was adapting well. For two weeks I wouldn’t allow him to cum So I told him we would celebrate. with a nice dinner and I would allow him to ut tonight. He looked like a child on Christmas morning but…..
When I showed him the butt plug he didn’t understand. I told him he had to wear it to dinner. Yes sir! Right up to his man pussy and it was to stay there until we got home. Like a good boy, he got it in there, and off to dinner we went. What he didn’t know was that it was a remote control vibrating butt plug and guess who had the control? Not Bobby, when the waiter came to take our order I turned t on and cranked it to high. You should have seen him trying to talk to the waiter. Then I smelled it. His semen. He came in his pants as I hoped he would. As we finished dinner he told me that was the most intense and gratifying night of his life. My response, “the night’s not over”
When we got back to the condo I informed him he was going to get his reward.
I broke out the 10′ BBC dildo that looked so real. I let him lube it up with both his hands while he begged me to fuck him. Once he spits out that butt plug I was up that man pussy in a flash. I wasn’t gentle I had 5′ in and he started crying. So I pushed harder. I got to where I was pulling out just to the tip and ramming it back in hard. Past 5′ now…6′, then 7′, then 8′, more tears but he was also screaming at me to fuck him harder! Once I had maxed-out at 10′ I just let my body weight keep it buried while both my hands stroked his cock until he came for the second time that night. I enjoy every minute I was pegging my sugar daddy. There is something in the way he screamed that really turned me on. after that intense second orgasm, I put some of the cum on my fingertips and slipped them in his mouth. There was no resistance from my pussy boy. He was now my cum eater as well. He was completely mine. Including his man pussy. Stay tuned or you can call me and I’ll update you later on his man pussy ongoing development.
