Pleasing Mr. Wilson Pt. 06

I watched Stan's pick-up truck go down the driveway. It was nearly dark now. We had a lovely date together, making love in a meadow on a hill overlooking the lake. It was Stan's first experience with a sissy crossdresser. He knew I was a femboi before we went out but I was worried that he might be turned off as things progressed. But it was quite the opposite. Once I get a fella's cock in my mouth they're always happy and begging for more!

Stan's cock was the biggest I had experienced so far. Enjoying his cock was wonderful but my love hole was sore and cum was was still dripping out of it into my panties. I stood there reflecting in the light of the porch lamp. I felt the warm glow of having been thoroughly fucked in my mouth and ass by a young stud. I entered the cottage where James awaited me.

"How was your date?" James called from the bedroom.

"I had a wonderful time, James. Stan is such a gentleman and he really complimented my looks. I think he enjoyed the evening as much as I did."

"I'm sure he did, Diana! Go get cleaned up and come join me."

I went to the bathroom to freshen up. First I pulled off my denim capris, noticing a damp spot in the rear. Then I peeled my panties off. There was big gob of Stan's semen in the crotch of the panties. I stared at the proof of my womanhood. I could smell the still-warm cum. I threw the soiled clothes in the laundry hamper and took a shower. My makeup was a mess so I just removed it. I gargled the taste of cum from my mouth before brushing my teeth.

Then I brushed out my hair and went into the bedroom to find something sexy to wear to bed.

"Close your eyes James," I teased. "I'm going to find something sexy to put on and I don't want you peeking!"

"No problem, Diana. I'll just sit here in bed watching TV."

My own lingerie collection was growing so I was using less and less of Mrs Wilson's clothes. I decided to wear a new negligee that arrived earlier today. The negligee was practically nothing - sheer, black and nearly transparent. There was silly black faux fur trim around the edges. There was a ribbon around the waist which I tied loosely.

From Mrs Wilson's panty drawer I selected a pair of cream-colored vintage style fullback panties which were nearly transparent but had a wide band of lacy flowers around the waist. My little stiffy would be very visible through the negligee and panties.

Finally I picked a matching bra from Mrs Wilson's bra drawer. The bra had big padded cups covered with lace and a little butterfly in the cleavage. The band was extra wide with lots of stretchy lace. The bra was perfect for holding my fake boobies in place and showing off my figure. A real woman might have not bothered with the bra and just let her tits hang softly under the fabric of the negligee, but I feel most feminine wearing big fake tits held firmly in place with a pretty bra that my lover can squeeze while he fucks me. Mmmmmm.

James motioned for me to join him. He was sitting with his knees up under the covers and pointed the remote to turn off the TV. He wanted to be able to put his full attention on his little sissy cocksucker.

I walked toward the bed twirling my negligee in a seductive way. With my big boobs swaying and the negligee tied around my waist, I really had a feminine figure. I loosened the ribbon around the negligee and sat on the bed beside James.

"You look sexy as usual Diana," James said. "I see your little cock is stiff again. Where's your chastity?"

"Stan took it off and I didn't put it back on - sorry."

"That's ok," James replied. "Go get a ribbon from the top drawer."

I fetched a pink ribbon and handed it to James. "Come closer, Diana."

I stood closer to James and he parted my negligee and pulled down my panties. "Let's try this," he said as he held the ribbon under my balls. James brought both ends of the ribbon up around my cock and looped around again. He did a couple of turns around the shaft of my penis and finished up with a cute little bow.

"There you go," James concluded. "A cute little sissy cock all tied up in a pink bow like a little girl."

My cock was so hard it ached and the ribbon around it was tight and kept my cock hard. I wanted to stroke it but didn't dare touch myself unless James told me to. The sexual tension and the constant desire to cum is a sissy's lot in life. I was happy as long as James was happy.

James gave my wee wee a little slap which hurt plenty on my swollen cockhead. "Ouch," I said.

"Don't be silly, Diana. Your cock is always sticking out looking for attention and I just gave you some," James laughed.

"So Stan removed your chastity - he must have gone crazy during your date. Tell me all about it."

"He was really sweet James," I began. "It took a while to get him comfortable with the idea of me being a crossdresser but he soon came around and I think he thought of me as a girl. Then he couldn't get enough!"

"We went to this field overlooking the lake. Stan spread out a blanket on the grass where we made out. When I first got my hand in his pants I remembered just how big his cock is. A big clean, cut cock. So I started off by giving him the best blowjob I could, but it was hard because I couldn't get much of his cock in my mouth. My jaw muscles are still sore from sucking him."

While I was talking James pulled away the covers and got on his knees facing me. I lowered myself onto my back and looked up at James and his cock and balls. His cockhead was glistening with precum. Instinctively I reached up to caress his balls. James responded by bending over and rubbing the tip of his cock all around my face, stopping briefly a few times at my lips which I opened hoping he would push his cock into my eager little mouth hole. But James just wanted to tease me.

"So Stan has a big cock," James said. "I guess you enjoyed it more than mine - isn't that right you little slut?"

"Oh James, it's not like that. Of course I liked his cock but I couldn't deep throat him and I nearly gagged a dozen times. I much prefer sucking your cock because it just the right size for my mouth and you've taught me how to deep throat which I love doing for you."

"Well you can suck mine now missy" and he pushed his boner deep into my waiting mouth. It felt so good to have James in my mouth again. I was so used to the feeling of his cock in my mouth and the feeling of the stages of the blowjob. I could feel his cum building and could control when he came and could decide at the last moment whether I wanted to take his load in my mouth or deep in my throat or just let him spurt all over my face and body. Of course James often held my head and directed his load wherever he wanted and I loved that too.

My description of my date with Stan clearly turned James on and he was really pounding my mouth with his hard-on. It was an uncomfortable position for me and my neck hurt but I kept doing my duty as James' substitute wife, happy to be giving him the pleasure and satisfaction he deserved.

James pulled his cock from my mouth and I quickly turned on my side and got more comfortable. "So you worked hard to give Stan a good blowjob. I bet he shot his load in your mouth quickly."

"Oh yes, he did cum quickly the first time," I replied.

"How many times did you make him cum?"

"Just twice - once in my mouth and once in my ass."

"After I sucked him off I gave him the key and he removed my chastity. The chastity and my cock were slippery with lube and he had a hard time getting it off and slipping my balls through the loop to remove it. I got lots of feeling up while he removed it. I think he enjoyed touching my cock but then he tucked it back in my panties. Later he let me stroke my cock until I came. So I had a nice cum too."

"So Stan really was a gentleman, and generous with your pleasure. You must have been happy, Diana."

"Yeah, it was nice. Then I encouraged him to play with my boi pussy and he did. Before long he was on top of me pushing his cock into my love hole. I was on my tummy with my legs spread apart. I held my bum cheeks apart for him to make it a bit easier. It was pretty uncomfortable when he finally started to get his cockhead into me. It hurt. I'm still sore. It felt like he filled me with cum when he came. It's still dripping out!"

James pushed my negligee aside and reached around to my bottom. He put his hand in my panties and gently massaged my love hole with his index finger. He slipped his finger inside me. "Your hole is so loose, Diana. You really are a slut! You're always spreading your legs for men, and parting your lips for that matter. You are a real cock-hound! Lie on your back so I can fuck you now!"

I moved to the middle of the bed and down onto my back. My negligee was open completely and my pretty bra and panties shone in the light of the bedside lamp. I spread my legs as James got into position between them. My ribbon-tied cock was sticking out uncomfortably between my legs. James pulled my panties down to the top of my thighs which is where I like them when I'm being fucked. I love the thought that a man's balls are cradled by my panties while his cock is enjoying my bum hole.

James was on his knees between my legs then bent forward onto his elbows with the tip of his cock between my bum cheeks. He began to slowly move his cockhead in and out between my cheeks which were slippery with lube and Stan's semen. I could smell the yeasty scent of Stan's cum. James' cockhead just grazed my bum hole at each stroke. I thought this was how he gently begins making love to his wife - and I was his wife for this moment. I felt so happy to be able to please this kind and sexy older man. I was his, for his enjoyment.

I reached down and tried to pull his cock into my love hole but James just pleasured himself more by pushing his cock through my grasp. I hoped he wouldn't cum before entering my hole.

After a few minutes of James thrusting and panting, he finally pushed hard at my opening and easily entered. There was only slight discomfort at the beginning. Stan's cock had done its job, stretching my hole wider than it had ever been before and ready for James' cock.

James started thrusting faster and faster. I wrapped my legs around him and tried to pull his body tighter to mine as he fucked me. I was sweating and panting too, feeling my fake tits flattened against his chest and feeling more feminine that I ever have. I was a dutiful wife enjoying every minute of her sexual duties.

But I felt like more than a dutiful wife, I also felt like a cock-hungry slut. I already had a load of cum in my ass from Stan and in a few minutes James' load would be pumped in there to mingle with Stan's. Two loads together in my boi-pussy. The thought excited my inner crossdresser sissy faggot.

Right on cue, James began to pump harder and grunted at each spurt of his load. I was a full woman in more ways than one!

When James finally stopped cumming, he collapsed his weight on top of me, sweaty with heart pounding. I relaxed my legs and wiggled into a position that allowed me to breathe a little. My partially pulled down panties were still stretched across my thighs, holding James' balls, my big fake tits squished between us.

"You really are something Diana," James whispered in my ear. "I could fuck you everyday forever."

"I'd love that James! Even after your wife gets home I hope you can find a way to keep fucking me. I can't bear the thought of not pleasuring you every day."

"Yeah. I've been thinking about that and I think I have a plan. But for now let's continue enjoying the privacy of my cottage. I think there may be positions we haven't tried yet!"

"By the way Diana, I meant to tell you that I have a surprise for you. Tomorrow."

"A surprise for me? I can't wait! What is it?"

"I'll tell you in the morning Diana," and James drifted off to sleep in my arms.

To be continued...