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Vanessa and Ken's Second Date

"A forbidden second date draws us closer."

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It had been a couple of weeks since Ellie and had our little trysts with Derek and Ken, and I couldn't stop thinking about it.  As much as I loved being with Ellie, there was something magical about that night with Ken.  We had talked about it, and I downplayed how wonderful it was to make love to Ken.  She told me that she enjoyed her night with Derek too, but she didn't really seem to make a big deal about it. 

 

I wondered if she was downplaying it too, but part of me didn't even care.  Maybe she was still thinking about Derek, but I was thinking about Ken.  It was taking all of my restraint not to call or text him.  This was supposed to be a one-time thing, but we exchanged numbers anyway.  

 

Then one day I got a text.  It said, "I can't stop thinking about you.  Let's meet."  I was shocked, and I didn't know how to respond.  I never wanted to hurt Ellie, but my desire to be with him again was too strong.  I sent him a message back that said, "I can't stop thinking about you too.  I need to be with you again.  Where and when?"  We went back and forth for a little while until we decided that a good time to meet would be a Friday night when Ellie would be out with her girlfriends.  I told Ken he could come to our place, but he would have to be gone by 1 am the latest.  Plenty of time for us to have some fun.  

 

On the days leading up to our date, I bought myself some new clothes so I would be all ready to get dressed up for him.  When the night arrived, I said goodbye to Ellie for the evening and went for my stash of clothes.  I laid everything out and hopped in the shower.  After shaving all my body hair off, I jumped out, dried off, moisturized, and was ready to get dressed.  I slid on a nice new pink Victoria's Secret thong followed by a pink garter belt, and bra. 

 

Then, I opened up a brand new package of nude stockings and slid them on.  I always liked the combination of pink lingerie and nude stockings.  Next, I put on my new blue dress.  It was short sleeved and came down to just above my knees.  I wanted to be flirty, but not too slutty.  Not yet anyway.  I sat at Ellie's makeup table and took my time making my face as pretty and girly as possible with sexy, smoky eyes, and light colored lipstick.  Then, I put on a long blonde wig and sprayed myself with Ellie's perfume.  My five-inch high heels were the last touch, and I was ready for company.  

 

I sipped a martini waiting for Ken to arrive.  I was nervous, and when the doorbell finally rang my heart jumped.  It was racing as I answered the door.  He stood there looking sexy as hell, and I invited him in.  He gave me a kiss on the lips to greet me, and my heart jumped again.  I got him a whiskey, and we just sat and talked for a little while.  We talked about likes and dislikes, politics, and some past relationships.  He had been an admirer of sissy girls for a long time, but he only recently worked up the courage to meet with one.  I was only the third he had been with, and he was realizing that he liked it better than being with a regular girl.  

 

After some time passed, we both seemed to be getting anxious.  He moved a little closer and put his arm around me.  I took the hint and moved onto his lap.  He kissed me slowly and deeply and put my arms around him.  We made out for a little while enjoying each other's lips and tongues.  I could feel his cock getting hard beneath my ass. 

 

Then, I felt his hand moving up my skirt.  He started stroking me through my panties, and I kissed him deeper.  His mouth moved to my neck, as his hand pushed my thong aside and his fingers started playing with my little hole.  He licked his finger and pushed it inside of me.  It felt so good to feel his big manly finger inside my little boi-pussy.  I moved my hips with his fingering and kept my lips locked on his with our tongues massaging each other.  

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He whispered in my ear, "You're so fucking sexy.  I want to make love to you Vanessa." 

 

I couldn't handle much more.  I stood up and took him by the hand to lead him to the bedroom.  Not a second passed before he was kissing me again, groping my ass and legs.  My arms held onto him tightly, and then my hand moved down to his hard cock, bulging through his pants.  He took off his shirt, revealing his sexy, muscular body, and I unbuttoned and unzipped his pants.  He took them off, leaving just his underwear and that giant bulge of his. 

 

I got down on my knees and slowly pulled his underwear off, revealing his beautiful shaft.  I looked up at him, smiling, and then I gave it a little kiss.  Then, a lick, and then another couple of kisses.  He moaned as I teased him with my mouth.  I licked around his shaft and tongued his balls before finally engulfing his entire cock into my mouth. 

 

"Oh god, Vanessa, yes!" he cried out as I sucked on his cock.  As my head bobbed up and down on him, my tongue flicked the head of his dick, and I played with his balls with my hand.  He put his hand on the back of my head and moaned louder.  His hips began to move to meet my mouth.  He was fucking my mouth and I was loving it.  

 

"I need to fuck you, Vanessa," he moaned.  

 

I looked up at him, still sucking his shaft, and kind of batted my eyelashes at him.  I stopped and stood up to kiss him again.  He led me over to the bed and laid me down.  He laid down next to me and kissed me again as he began to finger me.   Then he moved on top of me, spit on his hand, rubbed it on his cock, and placed it against my pussy.  For a few moments, he just rubbed the head against my hole, teasing me.  I loved it and it made me want his cock in me more than anything in the world at that moment.  

 

"Oh god, I need you.  Fuck me, Ken.  Put your cock inside me," I cried out.  

 

He slowly began to push into me so I could feel every inch.  I moaned like a little bitch until I felt his balls against me.  He kissed me again and then started to slowly and deeply pump his cock into me.  My legs were up as far as they could go giving him total access to my sissy hole.  I could feel him hitting my prostate with each stroke and it felt so wonderful.  I wrapped my arms around him as he fucked me deep and hard, bucking my hips against his strokes.  

 

"I want to make you my girlfriend, Vanessa," he whispered in my ear as he kept pumping into to me.  "I want you to be mine, and call me your daddy."  

 

I moaned and yelled out, "Yes, I'm your girl, daddy!  I'm your sweet sissy girl!"  

 

Then, I started to feel an urge to cum that I couldn't control.  He was hitting my prostate just right, and my cock started to spurt without even being touched.  My cum shot all over both of our chests and we could feel it on us as he kept fucking me.  Then, he couldn't wait any longer and his cock began to pulsate as he buried his load deep into my boi-pussy.  

 

He kissed me again with his cock still inside of me and I put my arms around him.  As he moved aside and put his arms around me and held me tight, he said, "I meant what I said.  I want you to be my girlfriend."  

 

I thought for a moment, not knowing what to say.  What about Ellie?  What should I do?  

 

"Have you thought about hormones?"  he asked.  "I would love for you to move in with me.  You could start hormones and maybe get some breast implants.  You would be so fucking sexy as my shemale girlfriend."  

 

We talked some more and decided we would think more about this.  We set up another date, this time at his place where we didn't have to worry about Ellie coming home.  I couldn't wait.  

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