In my first submission, "A Fantasy Fulfilled", I related the story of my attempt to partially fulfill one of my ex's fantasies of seeing me get fucked in the ass. Tracy's real fantasy was watching another man take my ass. She settled (happily I might add) for taking it herself with a dildo. She really enjoyed herself, particularly the control she had over me. She had always told me of her "penis envy", how it must be really cool to be a man and put a part of your body inside a woman and just fuck her. (Tracy was also bi-sexual, another little thing we never explored together.)
We never followed up on the anal sex because we were divorced a few months later. We remained friendly after our divorce though, and after a couple of years, when neither of us were in a relationship, we'd get together occasionally for sex. We had better sex on these occasions than we did during most of our marriage.
I hadn't forgotten her fantasy and I had a similar one of my own. I wasn't interested in allowing some guy to put his cock into me. I was intrigued, however, by the thought of letting Tracy do it. Being taken anally by a woman had interested me ever since the episode with the dildo and I decided to fulfill both of our fantasies at the same time.
I decided that Saturday would be the big day. I called Tracy on Monday and asked if she'd like to spend Saturday with me and have some "unexpected fun."
"What do you mean by unexpected fun?" she asked.
"Trust me. I promise you a fun day that you won't forget," was my response. "Come over around 1 o'clock and you'll see."
She agreed to spend the day with me and my preparations began. On Tuesday I went to the adult toy store to look for Tracy's phallus. I figured if I was going to let her take my ass, I was going to pick out the right strap-on. Not too big, not too small. I wanted fun and pleasure but wasn't interested in pain, you know? I chose one made of firm latex that felt very close to the real thing. "My" end was about 6 inches long and about 1 and a quarter inches in diameter. Not huge but not tiny. Tracy's end was about the same size and was curved in a way that would allow it to fit into her easily when she strapped it on. I also bought some lube (a large tube) and asked the clerk to wrap them up. She gave me a knowing look and put them in a box, then wrapped it in plain white paper with a red ribbon.
"Have fun," she said as I was leaving, giving me a smile and a wink.
"Thanks. I hope to," I said.
I bought a couple bottles of Tracy's favorite wine and some things for dinner, which I knew we would eventually need. I could hardly contain myself during those days before Saturday and masturbated several times during the week while envisioning the scene. God, I was really ready and wanting this!
Saturday finally arrived. I had cleaned the house and changed the sheets on the bed. The wine was cold and Tracy's gift was sitting on the coffee table. She knocked on the door at about 5 minutes to one. When I opened the door I instantly began to get hard. Tracy was dressed in extremely short, tight denim shorts and a crop top with no bra. She looked like a hooker and I knew she was in the mood for sex. Tracy was 5'2" tall, small boned with C-cup breasts and a great ass. She had been working for a landscape company in the Florida heat and had lost several pounds. Her stomach was flat and her legs body was absolutely incredible. Her long, curly, reddish brown hair hung down around her face and she looked beautiful and extremely sexy. I pulled her to me and kissed her deeply, our tongues swirling together and our hands roaming.
"Hi honey," she said between kisses. "How are you?"
"Hey Baby. I'm good. In fact, right now I'm great!"
Tracy smiled and stepped inside. I closed the door and locked it, my eyes glued to her ass. The shorts were cut right up to her cheeks, not allowing them to show but just barely. "You look really hot," I said. "Damn."
"Thank you Baby. I'm glad you like it. I wanted to get your attention," she replied.
"You definitely got it," I said, pointing to my groin. It was obvious I was getting hard and Tracy walked over and rubbed her hand up and down on my cock, giving me another kiss as she did it.
"Is this for me?" she asked.
"Later," I said. "I have something else in mind first. Would you like a glass of wine?"
"Sure. What are you up to?" she asked, giving me a sideways glance.
"You'll see," I said. "Trust me, you'll like it."
I went to the kitchen and poured two glasses of wine and took them back into the living room. Tracy was sitting on the couch holding her present in her hand.
"What's this? Did you get me a present?" she asked with a smile.
"As a matter of fact, I did. But you can't open it yet. Be patient. You'll enjoy it, I promise."
"I'm sure I will," she said.
"I think we should take a shower and get wet and slippery. What do you think?"