My Friend Ashley Ch. 06

I was intrigued but a little wary. Sheila is a very pretty brunette with a dynamited figure. I could not imagine her needing any more friends. She was smart, witty and had a great sense of humor. I decided to explore her instincts even though I had no idea what she was talking about.

"Okay. Give me your address in case I get lost. I will try to follow you, but you know rush hour traffic."

I followed her closely and managed not to lose her in traffic. When we got to her apartment, she invited me in.

"The pizza will be here in about twenty minutes. How about a glass of wine?"

I was fine with that and she opened a bottle of dry red. To say that Sheila was pretty would be an understatement. She was about 5'-7" tall and her heels were a little more businesslike than mine. She appeared to be about a D cup and had an enviable figure. She wore stockings which is a little out of the norm in today's office attire, but her legs were absolutely fantastic. The calves were well defined, but not overly muscular. We talked and I was wondering where this was leading. The pizza arrived and we each had a piece. Sheila said that the sauce from this parlor was fantastic and that it was a little messy.

"Do you want a towel?" She asked.

"Sounds good." I accepted the towel and the pizza was delicious, but indeed soft crust and messy.

"If it is okay with you, Ra'Chelle, I am going to slip out of my dress so I don't get any sauce on it."

"Sure, fine, I don't blame you. It is really good."

She kicked off her heels and removed her dress before picking up her pizza again. I did not notice at first. I was battling my pizza also. When I did look up, I noticed that she had on a sexy demi-bra and her cleavage was very prominent. I followed her body lines down to her waist which was encircled with a lovely yellow lace garter belt. This held up her off-white stockings. I noticed a pretty yellow bikini and a What?? A hefty bulge in her panties. Oh, my god, this lovely woman had a cock stuffed into those panties that was about to burst out.

I looked her in the eye in shock. I had no idea what to say. I sat in stunned silence.

"Everything okay, Ra'Chelle?" she asked.

I stammered. "Yes. Everything looks good."

"Would you like to take your blouse and skirt off, Ra'Chelle?"

That was it. She had made me. I wondered when she had noticed. Maybe I was deluding myself about passing. Maybe Ashely and Gretchen had complimented me too much and I was not as critical of my appearance as I should have been. No, that could not be. Many men were either fooled or didn't mind since I presented myself as a woman.

Either way, Sheila looked great. That cleavage was all real. Her face showed no signs of any masculine traits. Her legs looked better than mine and my legs were my best asset. Was she trying to fool me? Was that a fake cock in her panties? If it was, I would feel better. I was hiding a meager inch and a half of soft dicklet now that the hormones were shrinking my little clitty.

I stammered to answer. "How did you know?" I asked.

"I didn't for sure. Still don't Ra'Chelle. I guess it is a heightened awareness and my concern for always looking my best. You have that and are always looking at your makeup in the mirror. How about you take off your skirt and show me? I don't mean to be pushy and I do respect your privacy if you would rather not. I have been obsessing about you for so long and I could not contain it any longer. You are so pretty that I kept telling myself that I was wrong. Obviously, I don't share my secret with many people and I was desperate to get to know you."

She seemed genuine and later I was very appreciative of her fondness and attention. Right then I had to decide. Should I bluff and tell her she had me wrong? Should I huff out of her apartment and make her think that she was dead wrong? What should I do?

Going back to my basic core morality, I decided to do as she asked. I got up and removed my blouse then stepped out of my skirt. What was left were my bra, bikini panties and pantyhose. My dicklet was safely tucked away. She looked me over, paying particular attention to my cleavage. I assume she understood that I was tucked. Having real cleavage might have convinced the average man that I was a genetic woman, but not Sheila. Her eyes were sharp and she saw my panty profile, but still she was smiling and satisfied that her gamble had paid off.

"You are very pretty and perfect. I am impressed. I hope that I don't pry too much, but could you tell me if your breasts are natural, enhanced or transitioning?"

"Well," I said, "I might ask you the same thing."

"Fair enough. Growing up I always felt like something was off. My father was disappointed when I did not take to baseball, football or basketball. I wanted to play the piano. Since my mother was a talented amateur musician and singer, we thought that this was just the family genes working. During high school I developed an aversion to ugly boy clothing. I put down the impulse, but secretly was drawn to my mother's clothing. I am an only child."

"When I turned eighteen, I went to live with my maternal grandmother. The friction with my father had escalated to the extent that I wanted to get away from the conflict. The good thing for me is that my grandmother is filthy rich and I am the only grandchild. The move was ostensibly to go east and live with her while I was in college. Once I got away from home, I was free to dress as I pleased. My grandmother inadvertently found a pair of panties in my room when one of the maids noticed them behind my bed. Instead of placing them in the laundry, she laid them on my dresser and Grandma found them. She didn't pry, but somehow, she knew that they were not from a girlfriend. There was no evidence that I had a girlfriend. My interests were music and studying."

"Grandma was pretty hip and my grandfather had passed away years before. Grandma had some boyfriends, but no one stayed overnight in her big house. The family money came from her father and my grandfather was marginally involved in my great grandfather's business. My grandmother did not truly dominate my grandfather, but let's just say he knew where the bread was buttered."

"Back to me. Grandma managed to get me talking about school, girls, friends and just about everything. In a way she became more of a best friend. At some point she sensed that I was fighting my identify and thought I might be gay. It didn't matter to her, but she asked me what my deepest desires were."

"I could not come up with an answer. She suggested that I go to a psychologist friend of hers. She assured me that the information was strictly confidential and that she didn't want to know anything about it. After about three months, we got to the questions about sexuality, dating and all things in between. It was at this time after I felt secure with the doctor that I shared my uncertainness about who I was sexually. Over the next few months I managed to share that I was drawn to more things female than I was male."

"I was not an effiminent guy, I just loved everything about women. How we dress. How we wear makeup. Just everything feminine impressed me. I did not desire a sexual relationship with a woman. At least not then. I was doing very well in school. My friends were actually brainy girls. It was not romantic. I just liked the way they thought and how unpretentious they were. Sure, there was no shortage of beauty queens in the Ivy League, but that was not what I wanted for friends."

"And then, my grandmother died. In her will she left me millions of dollars, her house and the instructions to find myself and my happiness. She stressed in her will that I not be bound by anyone else's perception. My father was of course livid that my mother was not the primary beneficiary. She was well taken care of and my father still had his cushy job in the corporation. I was free to finish school or not. I did finish and got a master's degree. But I didn't need it. With the money and a secure trust fund, I never had to work a day in my life."

"But I was not wound that way. So, I finished college and explored my grandmother's wishes. I decided that I wanted to transition to a pretty girl and wear pretty clothes. I was thin and did not appear at all manly, so when I dressed as a woman, I made a pretty good picture. Not perfect, but passable even then. The only thing that was manly about me was my cock. I love my cock. It is big and thick and I could have made any girl a great lover based on my equipment. But I dressed girly and masturbated instead."

"After studying transition scenarios, I decided that I wanted not only to become a woman, but a pretty one as well. There were not financial constraints, so I set about finding a good plastic surgeon. I got some facial work done and then added these wonderful breast implants. Aren't they gorgeous? So natural looking. Some lower body work and I was set after about six months of recovery time. I didn't have anything else to do, so I set up a gym in my home and hired a personal trainer. I take a boatload of supplements, but no hormones. My cock is hard as a rock and I wear clothing to hide it. I might change my mind later, but for now I still love my big cock."

I was bowled over by her story and by her desire to get to know me. I was certain that it was all true and wondered aloud why she was working.

"Uh, the job is fulfilling, and I need to keep busy. I want a normal life and I am just getting to the point where I am embracing my feminity. Well, almost all my feminity if you don't count the elephant in the room. I am always refining my gestures, look and voice."

I noticed that her panties were completely bulged and her cock was making a tent. It was a sight to behold. I had seen some bigger cocks already in my new experiences, but nothing quite as sexy as a big cock stretching pretty panties. I was almost instantly jealous of her.

"Would you like to see it Ra'Chelle?"

Since moving in with Ashley I had had sex with at least three women. One straight. One Bi. One confirmed lesbian. I had sucked off numerous men. And big cocks at that. Now I was nervous about seeing a cock on a pretty gurl who had even better female characteristics than I possessed. It took me a few seconds to respond.

"Uh, sure."

"Oh, my god, thanks Ra'Chelle. I dreamed of this moment."

She placed her fingers under the elastic of her pretty panties and shimmied her hips while lowering them. Pop... Her cock sprang out and bobbed up and down. I was mesmerized. It was a gorgeous circumcised thick cock. It was almost eight inches long and thick. In addition, there was a pretty shiny glow about it. There was no way she could hide that sausage. I don't see how she would ever be able to wear pants or jeans. I almost lost my breath as she moved gracefully toward me. She placed her hand on my shoulder and leaned forward. Our lips met. We kissed. Her tongue explored my mouth. Our lipstick meshed together as we shared that intimate moment. Then she held her hand more firmly on my shoulder again and I sank to my knees...