My First Date with Kerry Lynn

This is the story about how I finally got up the nerve to kiss Kerry Lynn, a beautiful TransLady who I became enthralled with due to our relationship as COP/Prostitute; both of us working the streets. Make no judgements about her lifestyle; she was a beautiful person inward as well as outwardly.

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I was a seasoned police officer at the age of 35. I knew my way around the streets. I had seen my fair share of the ugly side of the city. In doing so I had met more than a few interesting characters. I knew most of the street people and had developed a friendly relationship with the girls of the night. The "Girls of the Night" also included several girls who were "Boys of the Night." Or should I say boys who were girls...or girls who were boys. Whatever you label people as, the labels quickly disappear when you get to know them. I had gotten way past my homophobic upbringing and racial barriers to learn that all people have personalities and all people have wants and needs and issues.

I had begun to find more similarities than differences between these "night people" and me. After all, we were both out there on the street at 2:00AM looking for something better. I had listened to their stories and knew them by their real names and given reassuring hugs to people who polite society had shunned. Sometimes, even when I was on duty and in uniform, one of these "ladies" would cop a feel (catch the pun there?) of my ass or crotch and snicker away into the night. One joke around the Police Department was that the best way to tell the male streetwalkers from the female streetwalkers is that the really pretty ones are the boys! We laughed, but it was so very true.

Such was the case with Kerry Lynn. Her hair was a perfect shade of blonde, long past her shoulders and naturally curly. There were no wigs; everything you saw was the real thing. Kerry Lynn was about 5'6", slim; her waist couldn't have been more than 24". Her legs were OMG picture perfect, always tan! Her face was the spitting image of Darryl Hannah. Her body was pretty damn close to that too! I don't know if I saved the best till last, but her ass was just absolutely beautiful. She could have posed in any gentleman's magazine and as a matter of fact she did get featured on a blue jeans billboard from a very prominent company. Nobody ever guessed that was a man's ass in those jeans.

Kerry and I had a unique relationship. Although completely professional, I had a special place in my heart for her and I think she felt the same toward me. If she ran into problems with some sort of street bully or another cop was harassing her, she would call me and I could usually get it all ironed out. Very often I gave her money just because I knew she needed it and maybe that was one less trick she'd have to turn to get by. I wanted better for her. Life had dealt her a harsh hand. She did not choose to be a transsexual; she did not choose to be gay or to live on the streets. She was born this way. If you had ever met Kerry Lynn, you would know that this person was in every sense of the word, a female. Her only physical contradiction to that was that she had no female breasts and a very masculine cock! But you could certainly not tell that from meeting and talking with her. She was ALL woman to everybody she met.

I had been working Detective Division for a couple of years when I got a call from a sobbing Kerry Lynn. I was working the "on-call" night shift so my schedule was pretty flexible and totally unsupervised.

Kerry Lynn told me that someone has stolen her car and that when she reported it to the officer working that beat, she gave me his name, he called her names; a faggot and a prostitute, and refused to take the report. That made me sick to my stomach so I researched it and found out that, sure enough, she had called the PD and reported an Auto Larceny. The beat cop responded and marked the call as "UL", which means "Unable to Locate" the complainant or reporting person and found no evidence of any incident at the reported location. That failure to perform his duties was handled...he got what was coming to him...but that's another story and I'm getting off track.

After talking with Kerry Lynn by phone again, I determined that she was at her house, alone, and yes, she still wanted to file an Auto Larceny report. With tons of unprofessional thoughts in my mind and in my pants, I told her that I am a police officer and I can take the report, however I would have to take the report in person. Since she was without a vehicle and her roommates were not home, I offered to come to her house and take the report personally. She asked for about 30 minutes to freshen up. I told her that I would be there in 30 minutes.

I had determined at that moment that I was finally going to find out what it feels like to kiss Kerry Lynn! I was SO excited! My cock was rock hard! I couldn't wait to get there. That was a long 30 minutes.

I arrived at her house and parked around back in the alley. I walked toward the door to knock and kept telling myself that I had be professional and take the report and do the victim advocacy form and all that stuff. But all I could think about was how beautiful Kerry Lynn is and maybe...just maybe we might take this relationship to the next level. I knocked on the door knowing that I was going to kiss her before I left. I had to let her know how I was feeling about her.

Kerry Lynn opened the door and she looked absolutely beautiful. I know I was staring because she said "Are you OK? Do you want to come in?"

Stuttering something, I found my way into the house. She was wearing a thin blouse that wrapped around and appeared to be held in place by one tiny little string. I was thinking to myself that there is a whole lot of sexy just under that string. Her old grey sweat pants were thin and worn and very tight, although not glued on tight. When she stepped around me toward the couch I noticed that her soft cock was swaying back and forth in her sweats and it was WAY bigger than mine is when I'm hard! She had always been dressed totally as a girl, so I had never known how big her cock was. I'm pretty sure I was staring at her crotch as her big soft cock swayed back and forth inside those thin pants. It was obvious that she wasn't wearing any undergarments and I was hoping that was intentional and purely part of her seduction of me. I had only seen her before in drag and she always had her cock tucked so that she looked more fem. She hadn't bothered trying to hide her true self from me tonight. I was mesmerized. She is honestly one of the most naturally beautiful women that I have ever known.

She sat down on her couch and I seized the moment and sat down right beside of her. It was actually a love seat, so it was a comfortably snug fit. I had on my suit with my shoulder holster under it, so my gun was pressed up against her. She said, and predictably; "Is that your gun, or are you just glad to see me?" I said "Don't worry Ma'm. I'm from the government and I'm here to help you." We both laughed and I got down to business.

I tried to keep focused on taking the report. Somehow I managed to do that just long enough to get all the required information. So I could write the report later.

I said "That takes care of all of the official business but there is one other thing I have to do."

Without giving her a chance to answer, I took her chin in my hand and turned her face toward mine and kissed her deep and long, right on the lips, our tongues swirling and ...and...oh my gracious what a kiss! I was hoping it would never end.

She seemed quite stunned as I stood up and took off my suit coat and my shoulder holster and laid them on the coffee table. I looked back at her, still looking stunned, and I took off my necktie. She grabbed it and pulled me back to her and as our lips met again, she threw my tie across the room.

As soon as I landed on top of her, I reached into her sweat pants and found the biggest cock I had ever seen! She was well over 8 inches. As my hand touched, and then explored the first cock I had ever touched, I knew immediately that I was going to love this. I explored her cock as it got harder and harder and grew to over 9 inches, maybe 10, I don't know. She felt so silky soft and smooth yet so firm and stiff all at the same time. Her cock seemed so much more masculine than mine, yet so feminine at the same time. I could feel every vein of her beautiful cock in the palm of my hand.

I don't think it was consciously, but I found myself maneuvering into a position so that I could take her cock into my mouth. I HAD to taste this beautiful woman's cock! I had never tasted one before, but I was not going to miss this opportunity. There certainly couldn't be anything gay about sucking the cock of one of the prettiest women I have ever seen!

Strangely enough as I lowered my head over her sexy cockhead, it was the sweet smell and silky feel that impressed me more than the taste of it. And then there was the size. This massive cock was slowly sliding into my mouth...MY mouth! It felt so fucking good! I couldn't believe that I was actually engulfing most of it. It was as if I was a natural born cocksucker. I remember savoring for a second, the feel of her cockhead as it was finally inside my mouth. Sucking her cock was the most natural feeling in the world.

At some point I realized that Kerry Lynn had managed to almost completely undress me as I was enamored with her cock. I looked at her, with her cock still in my mouth, just in time to see her wink at me as she took my much smaller dick into her soft mouth. Simultaneously she placed her hand on my head and pushed me back down onto her beautiful cock. The touch and force of her hand felt masculine on my head, just as her cock felt utterly feminine. I know I have never been that hard before or since! I thought I was going to ejaculate prematurely.

As I was playing with her balls with one hand and holding tightly to her cock with my other, she pulled her ass cheeks apart and guided my thumb into her asshole. It felt so much like a pussy that I had to look to be sure. Just then her asshole tightened up, her cock became rock hard and swelled to another dimension. She threw her head back off of my dick and moaned loudly. I thought she was trying to pull her cock out of my mouth, but when she did I pulled her tightly into my mouth and sucked even harder and deeper and she exploded into my throat and mouth. I was determined that my first blow job...especially since it Kerry Lynn, was going to be a total SUCKcess! I swallowed her cum as my own spurted out uncontrollably all over her neck and chest.

As I tried to catch my breath I heard her say, "What a nice gift on our first date. You gave me a pearl necklace."

I turned to kiss her I licked a big glob of my cum off of her chest and we shared a precious cum filled kiss.

My police radio blurted out my number as we stood together nude in her living room. As I answered it, one of her roommates entered the room and said "OH, you should have called me and told me to stay away. OOOOH! Kerry Lynn got her some Blue Dick, didn't she." She/he went on to her room.

As Kerry Lynn stood naked and still half hard in front of me; me back in my suit and preparing to go on another call...she kissed me again and asked: "Did you have this planned or was it spur of the moment?" I confessed, "I have wanted you for a long time...but tonight, I planned this. I couldn't wait any longer. I knew when I offered to come over here that I was finally going to kiss you. I hope you don't mind?"

"If you don't go right now I'm going to have to get plugged. Cum on back whenever you can. I've been told that I am quite 'a-dick-tive."

We had quite a long and beautiful relationship after that. Definitely some of the best sex I have ever had. She was quite a woman. All woman in my book!

I'm sorry we lost touch Baby. I hope life has been kind to you. Miss you!