With Guidance from Grandma

"I hope so too, Mistress Grandma."

My grandfather had passed away ten years prior from a heart attack. I would later wonder if his poor heart finally just gave way after being my grandmother's plaything for the thirty years they were married.

"We shall see. But enough teasing... I want to see you wearing my gifts."

On the bed were nearly a dozen boxes. She hadn't brought them on the plane with her. I knew she had gone shopping alone the day after she our first "encounter" but I never imagined it was to buy lingerie for me.

"Some of these items may not fit and we can return them. I plan on taking you shopping with me when you come to California to school." She paused to wait for my reaction.

"School? I... I don't understand..." I stammered.

A broad smile grew on her lips. "Another graduation gift. I talked to your parents, and they told me you wanted to study pre-law. I just so happen to have some connections, if you know what I mean..." She winked at me and smiled. "So, I was able to get you a 'scholarship' at a very good school that just happens to be a five-minute walk from my house." Again, she paused to see what my response would be.

My heart raced with excitement. I felt butterflies in my belly. My body tingled all over. The thought of living with her and being her submissive was overwhelming. Tears grew in my eyes as I was overcome with emotion. I actually began to sob.

"Shhh, come here sweetie." She said, holding her arms open to invite me in. I fell into her arms and buried my face in her neck. For several minutes she just held me tightly. "I take it that means you want to come live with me in California?"

I lifted my head up to look her in the eyes. I wanted to make sure she wasn't just teasing me. "Yes, please. You aren't joking, are you? Please tell me this isn't a joke."

"I would never joke about something like this. But there is one caveat. You will be living with me as Brandy, not Brian. The only boy clothes you will be allowed to have are those that you might want to wear if your family ever comes to visit or if you decide to travel home to visit. Of course, that would be your choice. If you want to see your family as Brandy... I leave that up to you."

Even in my heightened state of arousal, the thought of living as a girl made me hesitate. Could I do that? I was a boy. No, I was a young man. How could I? Nobody would ever believe I was a girl.

She saw the doubt on my face. Correctly, she determined it wasn't a matter of me not wanting to do it, but that I didn't think I could do it.

"Sweetie, let me assure you. I can have you looking and acting like a girl so much that even your own family would think you were a girl. Look at you, except for that hard, beautiful cock..." she paused as she stared at my erection. My grandma was lusting for my dick! "ahem... if not for this..." she reached out and grabbed it, giving it a nice hard squeeze which caused me to moan in pleasure. "Even I would think you were a girl."

For a couple of minutes she just stood there holding my cock. I was hoping she would stroke me or blow me or even fuck me... but she stood there holding my cock, looking into my eyes. "So, Brandy, would you like to come to California to live with Mistress Grandma?"

"Yes." I said, clearly under her control. "More than anything."

"You have made me very happy. Rewards will be coming your way. The first rewards are waiting for you to unwrap." With that said she guided me by my cock to the bed. "Open them in the order they are laid out."

The first package was a dozen pairs of panties. There were all kinds but what they had in common was they were sexy. Some were 100% lace and others had lace waistbands.

"I know how much you like lace." She said with a smile. "Open the next one."

The next few packages were more lingerie. There were teddies, including one that was almost identical to the pink one I was wearing when grandma discovered my lingerie fetish. When I opened it, she reached for the white lace panties I had opened earlier. Handing the panties to me she said "Put them on, and the teddy. The image of you wearing your mother's lingerie has been burned in my brain since I saw you that day."

I eagerly complied. Just like that day, my hard cock was barely contained in my panties. I felt so damn pretty and sexy!

"Just like I remember..." Grandma looked at me with lust. I didn't expect what happened next. She grabbed me, pulling me toward her she embraced me and then kissed me passionately. Her tongue ravaged my own. She firmly pushed me onto the bed. Pushing my panties to the side she gained access to my now painfully hard cock. I hadn't noticed when, but she had discarded her own panties. She climbed onto the bed with me. She squatted over my cock. With one hand she guided my cock into her drenched pussy. Her other hand was on my chest, not to hold me down, but to steady herself as she lowered her pussy towards my cock.

We both watched as my cock disappeared inside. She didn't stop until her ass rested on my hips.

"Oh yes, Brandy. That cock of yours isn't so little. It fills me up just fine." For a few seconds she just sat there looking down at me. "How does Mistress Grandma's pussy feel?"

"Unbelievable!" I had no words. For the first time my cock was inside another person. Just thinking about it almost made me cum.

"It gets better." She said as she started to ride me.

She was right. Her pussy fit me like a glove. It wasn't as tight as my hand when I jerked off, but it wasn't far behind. After not even thirty seconds of her bouncing up and down on my cock I felt my balls tighten.

"Mistress Grandma, I'm gonna cum if you don't stop..." I pleaded.

"I'm not stopping. But I want you to try really hard not to cum. Don't just surrender. Hold on as long as you can."

I did as she said. For a couple of seconds I thought i might be able to fight it off, but Grandma didn't do anything to help me. She not only kept riding me, but she also quickened her pace. Sensing my impending failure, she released me.

"Go ahead and cum for me. Fill up Mistress Grandma's pussy with your girl cum."

I exploded. My hips bucked like a wild bronco. My experienced grandma rode me like a professional rodeo cowboy. I didn't realize I had been moaning loudly the entire time I was cumming. My eyes were closed tight, I was seeing white even with my eyes closed.

When my orgasm subsided, she complimented me on holding off as long as I did.

"You did a great job Brandy. Now, good sissies clean up their messes." She then moved forward and squatted over my face. Lowering her pussy to my lips she commanded me to "Clean up your sissy cum out of my pussy, sweet little Brandy. Swallow that cum like a good girl."

This was one of my most recurring fantasies: a woman making me go down on her pussy filled with cum. In my fantasy, most of the time it wasn't my cum, but the cum of some stranger I never met. Don't take that as me being disappointed in what was going on. I was still amped out with desire.

"We are going to have so much fun together Brandy."