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.