It seemed the more time I spent with Carl, the more I enjoyed doing dirty things with him. The dirtier, the better. I looked forward to sucking his dick no matter where we were. Whether it was on a nice drive someplace, on a hike, or even in a theater, my mouth was always ready for his cum. I had also gotten used to taking him in my ass.
I was more used to controlling my sphincter to tease or pleasure him and would revel in pushing my ass into his body to take him deeper.
I was the epitome of a slut, wearing sexy lingerie or even other sexy things he liked. His favorites were a cheerleader and a Hooter's outfit. I fully embraced cross-dressing and looked forward to wearing sexy things he had for me. I felt transformed as I stripped off my boy clothes and slid pretty panties, slips, and hosiery on, my cock rigid in anticipation.
Often, Carl would watch me change, telling me to pose or move a certain way as he stroked his hard cock. I'd smile shyly and move close to him so he could feel my satin-encased body with his large hands. This always ended with sucking and mutual fucking, then a hot shower together. I was content with this routine and was always eager to visit Carl at his apartment.
After one evening of passionate lovemaking, Carl mentioned he wanted to introduce me to one of his friends. The thought excited me, and I wondered about being double-teamed by him and his friend.
Carl assured me that Henry was polite and discrete and I would enjoy meeting him. He said that I didn't have to do anything if I didn't want to, and I agreed to meet him.
On a Friday evening, I went to Carl's, and when I walked in, he introduced me to Fred. Fred was in his sixties like Carl and was about 6 feet tall with a slight belly and grey/brown hair. Fred shook my hand and then pulled me toward him, wrapping his arms around me in a firm hug. Fred released me, and I didn't know what to say as I felt his hands on my shoulders and his eyes roamed my body.
"Carl said you were cute; he wasn't wrong, that's for sure," Fred said.
I blushed a little and got a bit more red at this remark.
Carl told me, "I bought you some new things to wear, sweetie."
I walked down the hallway to the room Carl set aside for me and my clothes and saw a pair of Vanity Fair beige satin hi-cut panties, a matching bra, black thigh-highs, and a sheer black robe. My cock was straining as I dutifully took my boy clothes off and slid the pretty panties on. I was so nervous knowing a man I didn't know would see me dressed in such pretty things. I knew I didn't want to disappoint Carl and embarrass him.
Dressed, I looked at myself in the full-length mirror and made sure my rigid cock was contained in my panties before heading out the door to the living room where I heard Carl and Fred talking.
The talking stopped when I entered the room, and Fred let out a low whistle. "Well, don't you look adorable," he said.
Carl came over to me and gave me a hug and, with his left arm around my waist, said, "Robbie's such a sweet girl."
I looked down at the floor, embarrassed and blushing. I was standing there in front of two men wearing lingerie and ready to do who knows what. Another part of me was incredibly turned on and was bursting to pleasure both of them with my body.
Since I had met Carl, I had let him shave me totally bare and even paint my toenails. I was comfortable being a girl and making Carl happy.
Carl led me to the couch and had me sit down next to Fred and sat on my other side. Then he handed me a drink he had made me.
"Fred's retired and lives about 20 minutes from here; he used to be my neighbor," Carl told me.