Pleasing Mr. Wilson Pt. 02

I made two grilled cheese sandwiches for supper. I wasn't much of a cook, at least back then, so I was relieved when Mr Wilson took a bite and said, "this is quite good Diana. You're getting better in the kitchen all the time!"

I thought to myself, "I'm getting better in bed too!"

"Thank you Mr Wilson," I replied. "I'm glad you like it." Then I took a bite of my sandwich. I still had the faint taste of his cum in my mouth so was a bit sorry to spoil it with food. But I was hungry!

I reflected while we both quietly ate supper. I was grateful to have made love to Mr Wilson with my mouth this afternoon while dressed in his wife's lingerie. And I was proud when he told me the blowjob I gave him was special because his wife never let him cum in her mouth.

I was so happy to be able to dress up and look feminine, thanks to my slight stature and fine blond hair. I let my hair grow recently into an androgynous bob that looked quite fem when I was dressed. The light hair on my body was not very noticeable and I was slowly shaving off more and more of it. My legs, balls and bum were smooth as silk.

I was tingling with excitement as I knew I would be making out with Mr Wilson again at any moment. That was the great thing about having sex with men, they were always horny and ready to fuck or have their cocks sucked. Now, I liked girls too and went out on a lot of dates during high school. But the investment needed just to feel a girls tits or get her bra off was just not worth it. When I dressed up in a bra and panties, I felt I knew what to do for men and was willing to do it on the first date.

The pounding of the rain outside was louder than ever. Mr Wilson had just called my mom to tell her that it was too stormy for him to drive me home from his cottage. It was charming that Mr Wilson felt he had to take the responsibility to call my mom on my behalf, even though it was totally unnecessary as I had just turned 19.

"Why don't you call me James," Mr Wilson suggested suddenly.

"Oh, I'd like that Mr Wilson, I mean James," I replied. "Thank you, James."

It felt odd to be calling Mr Wilson by his first name, but it also made it feel as if we were on more intimate terms. I guess we were on intimate terms as I had just sucked his cock only an hour ago!

We each finished our glass of wine. "Why don't we go back into the bedroom, Diana?" Mr Wilson suggested. "You can do the dishes later."

"You're not done with me yet, James?" I teased. "I'd love to but first I'd like to freshen up and perhaps put on some different things". I couldn't wait to sort through Mrs Wilson's panty drawer again. I always seemed to find something sexy I hadn't seen before.

I put the dishes in the kitchen then went to the bedroom to examine Mrs Wilson's lingerie. I felt like going a bit more naughty for the evening. I found a pretty black basque with lacy frills around the bottom and the bust. I wondered if Mr Wilson ever fucked her in it? I knew the basque would make my bum appear fuller so I took off the garter belt and put on the basque and attached its belts to my stockings. I put on a lacy black bra that held my fake silicone titties nicely. Finally, I put on a nearly transparent black nightgown that was trimmed with lace. I reinforced my makeup with more, darker eye shadow and a little bit of red lipstick.

I brushed my teeth then called Mr Wilson in to join me. He came into the bedroom with a big smile on his face when he saw the new outfit I was wearing. I gave him a little twirl and bum-wiggle to tease him. The nightgown flared out as I twirled. I could already see a bump in his housecoat.

James sat on the edge of the bed and beckoned me to sit beside him. He put his arms around me and kissed my mouth. I leaned back to give him better access and I reached for his dick which was now poking out from the folds of his housecoat.

"Hmmmm, your cock is hard for me again James," I whispered in his ear. "How will I satisfy you this time, I wonder?" With that, I straddled his legs, facing him. Our cocks were touching again, both seeping precum. James moved his finger in a circular motion on the panty bump made by the tip of my cock. It felt nice. Then he tugged on a leg hole of the panties and slid his cock inside to rub directly against my little cock. I was in heaven! James put a hand inside my panties and grasped both of our cocks. He gently thrust his boner against mine while squeezing our cocks together with his big warm hand. I was close to cumming!

Then I slid off the bed and positioned myself on my knees between his legs. James pulled his housecoat open and spread his legs to give me better access to his beautiful cock and balls. I caressed his hanging balls with my hands and put them both in my mouth. I rolled my tongue all over his ball sack while grasping his shaft. Out of the corner of my eye I could see my reflection in a mirror, my head down between my man's hairy legs and my sheer nightie spread out on the floor around me. I felt very feminine doing a wife's duty with pride and contentment.

James started to moan and that was my cue to take the head of his cock into my eager mouth and start sucking in earnest. I struck up a rapid up and down motion with both hands grasping the base of his cock. His cock felt full and wonderful in my mouth and it tasted clean and fleshy. James took my head between his hands and guided my mouth up and down on his cock. I loved a man controlling my body and maximizing his pleasure. I tried to take as much of his cock as I could but gagged on only half of the shaft. I had work to do on my deep-throating skills but for now James seemed to be loving my blowjob.

When he got close to cumming, James lifted my head up to his and kissed me deeply on my mouth. "I'd like you get on the bed, Diana and lay on your tummy," he said.

I stood up in front of James and let my sheer nightgown slip off my shoulders and fall on the floor around my feet. Then I got up on the bed and put my head on my arms. I spread my legs slightly so he had access to my bum and anything he wanted. I felt my big fake tits squashed under me against the bed.

"You look very feminine Diana," James said. "Your ass is nice and round and I like your shaved cock - very cute!"

James began massaging my bum cheeks, gently touching my pucker hole with his thumbs. He paused, reaching for the lube and squirting some on his hand. After warming the lube between his hands he continued to massage my bum and finger my hole with his slippery thumbs.

I was glad I had been working my hole with a dildo every night for weeks so I knew I could take his cock. I was a virgin and it looked like I was going to give James my virginity tonight. I couldn't imagine a man I'd rather submit to than James. He was kind, handsome and attentive. He treated me like a woman and I was willing to play the part of his substitute wife, one who would please him more than his actual wife. A woman's pussy just can't compete with a boy's bum hole. I felt any man would like to fuck me, gay or not.

After a few minutes, I felt one of his fingers enter my hole soon to be followed by another. "How would you feel about me putting my cock inside you, Diana?" James breathed into my ear.

"Oh James, I want you to make love to me."

"Have you ever done this before, Diana?"

"No, I'm a virgin, James. I'd be so happy if you're the first to make love to me" I replied.

"I think I'm going to enjoy this Diana, I hope you do too".

"I've been practicing with a dildo for weeks James, I know I'm ready for you"

James straddled my legs and positioned his cock along my bum crack, sliding it back and forth on the sheer fabric of my panties. Then he pulled my panties aside and moved the head of his cock around my bum hole while pushing gently. He was going to make my hole yield. I gasped in pleasure and wiggled my hips in encouragement. I lifted myself up on my elbows and let my big fake titties jiggle in my bra. I hoped they wouldn't fall out!

"Oh James, that feels so good," I murmured.

"Lift up a little and I'll pull these panties down, Diana."

I lifted my bottom up and James pulled the panties down from my bum, but thanks to my garter belts he could only pull them down to the top of my stockings. I was happy about that because I feel most feminine when wearing panties - even when they are askew or partially pulled down.

James slid his slippery cock between my bum cheeks, pushing hard on my hole each time his cockhead touched it. I tried to relax my hole hoping to help ease his cock in. After a few minutes James stopped and repositioned himself on his knees across my legs. He grasped the base of his cock with one hand to make the head as hard as possible. He began to push the head of his cock hard on my hole and it began to yield.

"Oh James!" I cried. "Please keep pushing, I'm ready, you'll see. Fuck me darling!"

As James pushed harder my slippery little pucker hole began to give way. My head was spinning, knowing that a handsome man was beginning to take my anal virginity - he was making a woman of me, a fantasy come true in real life here in his bed where he'd fucked his wife dozens of times and now it was my turn. I relaxed on the bed on my tummy, feeling my big fake titties squashed on the bed.

James was gentle and considerate as he overcame my bum hole's resistance. Finally, his cockhead entered and then he continued to push slowly but forcefully as his cock found it's new home inside me. I felt some discomfort but it felt good overall.

"Is it okay, Diana?" James asked with concern.

"Oh, yes," I gasped. "Your cock feels so good inside me, so full. Please fuck me and enjoy my ass as much as you can, darling".

I loved talking to James as if I were his wife. He repositioned himself on top of me with his legs between mine. He slowly began moving his cock in and out of me as I tried to match his rhythm with my body.

"God, your ass is so tight, Diana," James gushed. "My cock has never enjoyed such a tight pussy! I don't think I can last long".

"Please enjoy yourself and fuck me as hard as you like James," I replied. "I want you to be satisfied, and you can fuck me as many times as you like tonight, darling."

He slowly increased his tempo and drove his cock deeper and deeper into my pussy-hole. I moved with him to increase his pleasure and in doing so was rolling on my big fake tits - I loved it! I was thrilled to feel James' balls bang against my ass as he fucked me. I felt like a busty teenage girl, like a slut, like a gay faggot crossdresser who wanted nothing more than to be a man's cum-hole.

James pounded me harder and harder until he started to grunt and I could tell he was spurting his load into me.

Then the grunting and heavy breathing subsided and his pumping stopped as James relaxed and put his full weight on top of me. I could feel his heart pounding hard. I was finally a well fucked femboy!

After a few minutes, James rolled onto his side and kissed me fully on my mouth. I put my arms around him and pulled him close.

"That was probably the best fuck I've ever had, Diana. Thank you," James whispered in my ear. "My wife is great in bed, believe me. But her pussy can't compare to your tight little hole, Diana. I'm grateful for the pleasure you give me. And I want to pleasure you too."

"Oh James, my pleasure isn't important but you can do anything you like to me for your own pleasure," I replied.

With that James put his hand between my legs and pulled my little cock into position for stroking. Of course my cock was hard and he started to jack me off with his big strong hand. I started to tremble and shot my load onto his arm in no time at all. Then I curled up next to him with my head on his chest getting semen all over my bra. I would have to do a lingerie wash tomorrow, but for now I was basking in the glow of having been beautifully fucked for the first time and knowing that I had satisfied a handsome married man.

I wondered where this was all going but I sure hoped James would continue to enjoy my body and teach me how to be an obedient femboy.

To be continued...