Pleasing Mr. Wilson Pt. 05

Stan guided my mouth to his with one hand and felt my tits with the other. He cock was getting hard again! What a horny stud!

As we made out Stan's hand began to explore my legs and tummy. He felt my panties until he pushed his hand between my legs and gave my chastity bulge a little tug.

"Wow, you really do have a cock, Diana. It's hard to believe, you look so feminine."

I responded by kissing him harder and wetter.

"You know, I don't mind if you unlock the cage thing," he said. He fished the key out of his pocket and handed it to me.

"That's so sweet Stan, I'd love to be unlocked. But it's not my place to unlock myself. That's for you to do, and I handed the key back to him.

"Unlocking a sissy girl's chastity is a man's way of rewarding her." I spread my legs to give Stan access to my chastity. With his big fingers Stan pulled the gusset of my panties aside revealing my cute little pink chastity. He lifted up the little lock and inserted the key. The lock came off but the chastity device was still looped around my balls. I let Stan figure that out as he gently held the panties aside and removed the cage. He ended up getting a good feel of my cock in the process which brought a smile to my face.

Stan handed me the chastity, lock and key and I put them in my purse. My little cock got hard immediately and was sticking out of my panties. Stand stared at it. "You have a cute little cock, Diana. It doesn't bother me to see it. Then he took my cock between his fingers and tucked it inside my panties where it made a nice little bulge under the lace.

Then Stan started to unbutton my blouse. I was happy to show off my pretty white bra heavy with fake titties. I helped him get the blouse off.

"I can't get over how pretty you look Diana," Stan said as he looked into my eyes. I smiled and kissed him again.

I interrupted the kiss and got the bottle of lube from my purse. I squirted some on my hand and reached behind me, putting my hand in my panties and lubbed up my crack and bum hole. I was sending a pretty clear message to Stan that he could put his cock in me if he wanted to.

"Let me put some lube on your cock Stan," I said as I dribbled lube all over his cockhead and my hand that was squeezing his shaft. Then I used both slippery hands to slide up and down his big boner. I lay on my tummy with my head close to his cock and lovingly jacked him off. He was super hard again!

"You can get on top of me and fuck my bum hole if you like," I said in my most feminine voice. His cock was bigger than James' so I was a bit worried about the discomfort to come but I was determined to give Stan everything I could.

"I'd like that Diana."

Stan got up on his knees behind me and started to pull my panties down. They were fullback style, sheer and transparent on the back and showed off my plump little bum.

"Just pull my panties down a little, just enough so you can get your cock in. I like to keep my panties on when a man is fucking me. It makes me feel more feminine."

Silently Stan tugged my panties down to the top of my thighs. I still had the garter belt on even though I wasn't wearing stockings. He must have wondered what all that lingerie was about but it sure made me feel sexy.

Stan straddled my bum and pushed his enormous slippery cock into the crack. Pushing his cock down with one hand Stan moved his hips so his cock slid up and down my ass crack. His cock felt warm and wonderful as he enjoyed himself.

I guessed Stan was too shy and inexperienced to know what to do next so I reached behind me and grasped his cock in my hand and guided it to a stop at my love hole. "Put a little pressure on my hole Stan," I said as I held his cock.

Stan moved forward and got the tip of his cock in a good position to push into my hole. I reached back with both hands and pulled my bum cheeks apart to help with the entry.

"Grasp the base of your cock to make the tip as hard as possible. That should help you push it in."

Stan did as I suggested and slowly put more pressure on my hole. Pressure - relax. Pressure - relax. He was making progress against the resistance of my love button which was beginning to succumb to him.

Suddenly his cockhead began to enter as my love hole yielded to the pressure. I gasped as it hurt quite a lot but it was tolerable. "Keep going gently," I said into the blanket.

Eventually Stan's cockhead was fully inside me and the discomfort lessened. He was motionless for a moment. "Your asshole is going to spoil me for the rest of my life, Diana. It's so tight and hot, I can't imagine a woman's pussy feeling as good."

That was music to my ears. "Oh Stan, please enjoy me as much as you like. Give me a good hard fucking, I know you'll love it."

With that, Stan began to move his cock in and out of my hole. The feeling of all that cock moving inside me sent waves of pleasure through my body. I wondered if I was having a female orgasm.

Stan's rhythm slowly increased until he was fucking me hard and moaning with pleasure. For me the discomfort was completely gone and the feeling of his cock inside me was pure pleasure.

I hoped he would last a long time inside me since I had already made him cum, but Stan was such a horny young buck that it wasn't long before he started grunting and pumping me full of his seed. He had a big long orgasm then he collapsed on top of me.

"That was fantastic Diana," Stan whispered in my ear, "Thank you. I can't believe how good sex is with you. You're amazing!"

I lay there on the blanket in the meadow enjoying Stan's heat and weight on top of me. With my tits squashed beneath me, the taste of cum in my mouth and a big load in my ass, I felt a complete woman. I was doing what I wanted to do - giving men pleasure.

It was beginning to get dark now. I saw a bright star low in the sky. Venus, perhaps. Goddess of Love. How romantic.

We both sat up. I could feel some of Stan's load drip out of my love hole onto the blanket. A nice souvenir for him!

We held each other and kissed passionately. Instinctively my hand went down to my stiff little cock and I started rubbing it. As Stan kissed me with his tongue I stroked my cock faster and faster until I spurted cum all over his legs.

"Oops, sorry about that!"

"No problem Diana. I'm surprised, but I don't mind your cum at all. He scooped some up with his finger and put it to my lips. His finger was nearly the size of my cock. I licked the cum off his finger and he scooped up another taste for me.

"You could almost turn me gay, you know."

"No need for that Stan, I'm happy just being feminine for you. If I can give you the illusion that I'm a woman but I suck you and fuck you better than a real woman then I'm happy. I'm gay enough for both of us, you just be yourself."

"Well, you're a helluva a woman and a helluva fuck!"

"Thank you for the compliment, Stan. I hope we do it again soon!"

"I better get you home, Diana. By the time I get you back it will be 10. I don't want to get in trouble with Mr Wilson!"

"Ha ha, he's happy you took me out, Stan. He will want to know what we did tonight. What do you think I should tell him?"

"Holy crap, I don't know! But don't tell him I fucked your brains out!" We both laughed.

We got up and put our clothes back on. Stan used the blanket to wipe the cum off his legs.

We held hands as we walked back to the truck. We had a lovely drive home with a spectacular red sunset. What's that expression - 'Red sky at night, sailor's delight'? It was certainly a delightful evening for me and I couldn't wait to tell James all about it!

To be continued...