My First Time with a Shemale

As my 30^th birthday approached, my wife Eva told me she had a special surprise planned for my birthday. She said she thought I was going to really enjoy it. Later I overheard her making reservations at a French restaurant that had recently opened to rave reviews. I was eager to try it. I thought I knew what my surprise was going to be.

My birthday fell on Saturday. Eva and I slept late. After we showered, she prepared a fabulous brunch, to which she added a generous helping of mimosas. During brunch, she mentioned that her co-worker, Cathy, would be stopping by later to drop off a file. I had met Cathy before at company functions and house parties hosted by Eva's colleagues. Cathy was a very pretty redhead who stood about 5'6". She was always elegantly dressed. She had a gorgeous body, but the feature that really caught my eye was what I considered one of the sexiest butts I had ever seen. I found Cathy quite attractive, something I was pretty sure Eva knew. I was not the least bit disappointed to learn she was coming.

Shortly after we finished cleaning up the brunch and loading the dishwasher, I heard the doorbell ring. Eva said, "That must be Cathy. Would you get the door sweetie?" I opened the door to find Cathy standing on the step. She was wearing a tight black dress that landed about mid-thigh and sexy high heels with a two-inch heel. She looked fantastic! I thought she must be just getting home from her night out.

I invited Cathy in. I deliberately offered her a seat on the sofa thinking it would cause her skirt to ride even higher giving me a glimpse of more of her shapely legs. I offered her a mimosa, which she accepted. I went into the kitchen to prepare her drink and another round for Eva and me.

When I returned, I found that Eva had joined her at the other end of the sofa. I handed Cathy and Eva their drinks, retrieved my own, and sat in a chair chosen because it was located to give me the best view up Cathy's skirt. We began chatting. Well, to be fair, Eva and Cathy did most of the talking, mostly about work-related matters. Meanwhile I admired Cathy's legs and tried to look up her skirt without being obvious about it. Glasses emptied quickly and I made another round. Fifteen minutes later Eva asked me to fix another round. By this point I was getting pretty buzzed. "Great 30^th birthday so far," I thought to myself as I headed to the kitchen to prepare another round of drinks.

I returned holding Eva's and Cathy's drinks. I went to Eva and held out her drink. Instead of taking the drink, she leaned forward, reached out, and grabbed my crotch. I was so surprised I just stood there. My cock began to harden. She fondled my cock and balls through my jeans for a bit. Then she grabbed the top of my jeans with one hand and the zipper with the other. She opened my zipper, undid my belt and the button holding my jeans close, reached in and pulled out my stiff cock. She pulled me closer. Then she took my cock into her warm soft mouth. I let out a small moan and glanced over at Cathy. She didn't seem the least bit shocked by this unusual development. Instead she had a little smile on her face.

For the next few minutes Eva gave me a wonderful blow job as I stood there still holding a drink in each hand. Eventually, she pulled her mouth off my cock. She looked over at Cathy and said, "I'm sorry. I'm being an awful hostess. Would you like some of this, Cathy?"

"Yes, I would, as a matter of fact," Cathy replied.

Eva took her drink from my hand. "Take Cathy her drink, dear."

I walked over to Cathy. She took her drink and set it on the table with one hand as she grabbed my cock with the other. She leaned forward and quickly swallowed my cock. What followed was exquisite blow job that included some amazing deep throating. Cathy would pull all the way to the end of my cock, swirl her tongue around the head, and then suddenly take all of it into her mouth, bobbing her head back and forth until I was about to cum. Then she would pull off again and start over. Meanwhile she was massaging my balls with her other hand. I was in heaven. I was getting a fabulous blow job from this gorgeous woman I had lusted after for some time.

"Does that feel good, sweetie," Eva asked.

"God yes."

"You're willing to return the favor for Cathy, aren't you?"

With visions of eating Cathy's pussy dancing in my head, I quickly replied, "Oh, yes. I'd love to return the favor."

"Oooh, I'd like that," Cathy said.

By this point, my jeans had fallen around my ankles, making it difficult to move without tripping. I quickly stripped off my clothes as Cathy stood. I moved to her and we kissed. My left hand found her right breast. It was medium-sized -- maybe a 34C cup -- and I could feel her nipple harden. I could tell she was not wearing a bra. Cathy broke the kiss and turned her back to me. "Unzip me," she said.

I unzipped her dress and slowly slid it down her body. I ended up on my knees as I lowered her dress to the floor. Staring me in the face was her glorious ass framed in a lacy black thong. I leaned forward and planted a wet kiss on each cheek. I hooked the top of the thong with my fingers and slid it down her long shapely legs to the floor. I couldn't resist spreading her cheeks and flicking my tongue across her rosebud.

"My goodness, you are a nasty little boy, aren't you," Cathy said. To answer her question, I gave her asshole a couple more quick licks.

Cathy stepped out of her dress and turned around. Instead of the pretty pussy I was expecting, a very hard, very erect cock was staring me in the face. It was about seven inches long, of average girth, and circumcised. She was completely shaved. I froze in surprise.

I heard Eva get up and come to stand behind me. She said, "Now, Joe, you promised to return the favor for Cathy. You can't break a promise." I felt Eva's hand go to the back of my head and gently press it forward. I was incredibly turned on. I opened my mouth and surrendered any resistance to Eva's prodding. In a moment I had the head of Cathy's cock in my mouth. "Oh, God," Eva said, "that's what I wanted to see."

I wrapped one hand around Cathy's cock and began moving my mouth up and down her cock. I was amazed how hard, yet soft, it felt in my mouth. I swirled my tongue around the head. I quickly found myself getting lost in the pleasure of sucking Cathy's cock. I took more and more of it into my mouth. I tried to give Cathy as much pleasure as she had given me. I began playing with her balls with my other hand. I pulled my mouth off and really looked at her cock. I told Cathy I loved sucking her cock. Then I tried to deepthroat it, taking in as much as I could. I found that if I moved quickly and let it slide down my throat, I could swallow almost all of her delicious cock.

Eva knelt beside me where she had a good view of Cathy's cock sliding in and out of my mouth. "Oh, God," she said, "you look good with that cock in your mouth." Soon I felt her hand slide over my ass to my asshole. I could feel her apply some lube. Then I felt her slide a finger into my butt.

Eva knows I enjoy having my ass played with. She had recently introduced the occasional strap-on play into our sex life. Her finger felt great while I continued my efforts on Eva's cock. Soon I felt a second finger enter me. Then a third with some more lube. I couldn't believe the situation. Here I was with the cock of one gorgeous woman in my mouth while another gorgeous woman was fingering my ass! I felt like a nasty slut. I had never imagined myself in this position, but I was loving every minute of it.

"I want to see Cathy take your cherry," Eva whispered into my ear. "I want you fucked. Ask Cathy to fuck you."

Suddenly I understood the recent strap-on play. Eva had been grooming me for this very moment. I reluctantly pulled my mouth away from Cathy's cock. I looked up at Cathy and said, "Please fuck me, Cathy."

"Louder, Joe. I didn't hear you," Cathy replied.

"Cathy, please fuck my ass," I answered louder. "I want to feel your cock in me." I quickly got on my hands and knees with my ass pointed toward Cathy.

I watched as Cathy slipped on a condom. Then she knelt behind me, rubbing the head of her cock against my rear opening. "Do you want to be my bitch, Joe?"

"Yes, Cathy, yes. Make me your bitch. I want your cock. Please quit teasing me." I couldn't believe I had just said that. Even more incredible, I meant every word of it.

I felt Cathy line the head up with my opening. Slowly she began to slide in. I could feel the head stretching me open. She kept pushing forward until finally I felt the head pop in. Cathy's cock was slightly larger than Eva's strap-on. It hurt just a little, but felt oh so delicious. She stopped and gave me a moment to adjust. Then she began slowly sliding it in. She would slide in a little deeper, then pull back. With each stroke she slid in a little deeper. Finally, I could feel her pressed against my cheeks and knew she was in all the way. She set up a rhythm and began fucking my ass in earnest. It felt wonderful! I reveled in the feeling of being stretched and filled. And as much as I enjoyed the strap-on play with Eva, I had to admit that the real thing felt even better. I began pushing back to meet Cathy's thrusts, trying to get her cock deeper into my ass. I heard myself moaning softly.

Eva moved to where she had a good view of Cathy's cock sliding in and out of my ass. She reached into her pants and began rubbing her pussy. "That's it, Joe," she said. "Take that cock; take it deep in your ass. Show Cathy what an ass slut you are. If you make her feel good, maybe Cathy will come back sometime and fuck you some more. Maybe she'll even bring a friend or two."

After about ten minutes, Eva reached over and took my cock in her hand. She began stroking me, matching the rhythm of Cathy's thrusts. "Cum for me, Joe," Eva said. "I want you to cum with Cathy's cock in your ass."

I could feel my orgasm building. Soon I cried out as one of the most intense orgasms of my life ripped through me. My cock spurted what seemed like endless streams of semen. I felt my sphincter tighten around Cathy's cock as I came. That must have pushed her over the edge. I felt her cock swell as she pushed as deep as she could. She let out a groan as I felt her cock twitch. I knew she was cumming deep in my butt. I realized I was happy I had made Cathy cum. Next, I heard the unmistakable sounds of Eva enjoying her own orgasm.

Cathy pulled out and we all sort of collapsed. Eventually we all finished our drinks and got dressed. Cathy gave me a big wet kiss goodbye as she reached down between us and fondled my cock. Then she left. "Happy birthday," my wife said. "I hope you enjoyed your present."

"I did," I assured her, "very much."

I later learned that Eva had long known that Cathy was transsexual. She was also aware that I thought Cathy was hot, a situation she found amusing. She soon realized the situation presented the perfect opportunity to fulfill her long-held fantasy of watching me suck cock and get fucked in the ass. She approached Cathy with the idea over drinks one evening after work. Cathy quickly agreed. On the way home, Eva stopped at a sex shop and bought a strap-on and harness. Eva told me that she enjoyed the experience even more than she had imagined. Something tells me I will be seeing a lot more of Cathy in the future.