All in all, I consider myself to be a pretty good judge of character. I rarely make mistakes when it comes to first impressions, and I like to think that I am fair and nonjudgmental when others meet me, too. I'm pretty easygoing, and I like to put people at ease when they make my acquaintance. That's probably why I have a fair number of friends, and people generally trust me and confide in me.
By the same token, I've made my share of mistakes and have had my share of successes as have we all. And also, like everyone else, there are parts of your life that you enjoy reliving and parts you'd wish you'd never experienced. But if you think back on your life they are, on a few rare occasions, one in the same.
I met Janice through friends about 2 years ago. She is a very attractive woman, a real knockout about 5'3" tall with light brown hair and green eyes. Her figure was perfectly balanced to the rest of her body, nice enough up top, nice legs, etc. When I met her for the first time we hit it off, but she was involved with someone so I pursued it no further. I never met her SO Chris and I wondered why since she was quite a prize. She was a great dancer and looked absolutely adorable in her typical flowered sundress. Not to mention she was well read, well traveled, and had a very cosmopolitan demeanor. It was clear to anyone that met her that she was not some girl next door; she was a social butterfly and could light up a room just by walking by.
During the winter she had a falling out with Chris. A few months later, I was unattached so I asked her out & she gave me the typical "let's just go out as friends" routine. I obliged her and treated her to a walk on the beach and a nice dinner at my favorite Chinese place. I fumbled through my chopsticks and enjoyed the conversation decidedly more than the food. She was also fluent in 4 languages, one of them Chinese, which made dinner interesting since she could actually order in Chinese. I was quite impressed.
I don't live that far from the beach, and we had parked at my house, so we started back to my place. It was a beautiful spring evening and the salt from the beach filled the air with that unmistakable brackish scent.
"Jakey, I loved that restaurant," she said. "It reminds me of a Chinese place back home." Despite our dinnertime conversation, the past didn't come up much. "And where might that be?" I asked. "Far away. Minneapolis."
"Yikes! Chilly winters, eh?"
"Yeah, but not so bad when you have someone to share them with," she smiled.
"Here we are," I explained. "Tera." We laughed at the mockery of my less than palatial estate. I bought a "fixer upper" house several years earlier. It's still a fixer upper.
"I think it looks great!" she said. "Want to come in? I have running water, floors, all the toys."
I could tell by the way she turned her head away the answer was no, but that was OK. We were going out as friends.
"Jake, let's not confuse this. We're friends and I don't want to ruin that."
"Hey, fair enough, Janice. I had a great time and maybe we can do it again."
"Yeah, sure, we can. I just need to..." she trailed off. "Umm, what?"
"Well, it's a long complicated story. Let's leave well enough alone for now, OK?"
"You got it. I'm going to be out of town for a few weeks, Janice. Do you want to get together when I get back. Dinner?"
"Yes, I do, Jakey. Sounds good to me."
"OK, I'll give you a call when I get back into town."
As I bent over and gave her a kiss on the cheek I thought to myself, "She's never going to go out with me again." But that was OK, too. We were still friends and that was important to both of us.
* * * * *
For the next two weeks I caught myself thinking about her quite often. I was really looking forward to going out with her again and I was anxious to see if she would want to oblige me. The evening I arrived back home, I pushed the front door open, careful not to dislodge it from its hinges. On the floor, amidst a pile of junk mail and bills, was a yellow envelope with "Jakey" on it. I opened it up and it was a card sprayed with perfume, or at least it smelled like it was.
It was blank except for the inscription:
Hope you had a safe business trip. I never thanked you for dinner.
PS Give me a call when you have some free time.
Free time? For a hottie like her all my time was free time. But not to seem overly anxious, I waited til about 9:00 pm to nonchalantly give her a call. I got her answering machine and left a message that I was indeed, back home safe and sound and to call me back when she had a chance.
About 10:45 the phone rang.
"Oh, I hope I'm not calling too late," she said. "No, no not at all. Still unpacking. What are you up to?"
"Just thinking about having dinner again. You may think I acted like a real jerk the other day refusing to come into your house, but I have my reasons. I am at a point where I really need to trust people to get close to them, and that takes time."
"Janice, you don't have to explain. That's fine. Take all the time you need. We're just friends, right?"
"Yeah, well, that's the part that I didn't plan on. I mean, we've known each other for over a year, but we have always been just friends."
"I know what you mean. But I do have to admit that I am attracted to you. I like you and I am attracted to you."
"I'm attracted to you, too, Jake, but there are so many things that you don't know about me. I'm afraid that you would have a hard time if you knew..."
"Knew what? That you took drugs a few times? You've been arrested? I can live with that stuff, but if you had something to do with that Lindberg baby thing, I mean, that's going to be a whole other ballgame" I laughed out loud.
"How do you do that?"
"I'm trying to...oh, forget it!" she chuckled under her breath. "You're not serious very often are you?!"
"I am when I have to be, but not usually by choice."
"What are you doing tomorrow night?" she asked. "Probably something with you by the sound of it."
"I'll be over at 8:00," she laughed. "See you then."
And that's how it stayed for about 3 months. We'd have dinner, see a movie, a play, whatever. We simply and incredibly enjoyed each other's company. She was witty, intelligent, fun. I was starting to fall for her. We talked a lot about animals, art, people's prejudices, kids, architecture. We covered innumerable topics and found that we had, for the most part, pretty similar views. I mean, about as similar as they will be for any two progressive-type thinkers.
One Saturday afternoon she drove up in her little '60's vintage Corvette convertible, sunglasses and bonnet notwithstanding. She had no idea how good she looked. I was in the middle of a "house project," but twisting my arm was an art she had honed to a fine perfection.
"Where we goin'?" I asked. "Just hop in. My turn to take you out."
We drove for about an hour way out of town, up the coastline. Eventually we pulled off onto a side road and slipped into what appeared to be a deserted golf course or field of some kind.
"I used to live near here," she explained. "My private party area. I love to come here because there's usually no one else around. Great place to read."
She opened the trunk and took out a wicker basket and the requisite checkered red & white tablecloth. We spread it down & unpacked the goodies which included an excellent '85 Chianti. The first bottle was gone in what seemed like minutes. Good conversation is a time accelerant, it seems. As she opened the second one, she asked, "Have you ever had the wrong idea about someone?"
"Oh, no here we go again. Janice, will you relax? I like you for who you are today not for what you have or haven't done. I enjoy being around you and nothing past or present can alter that."
"It's not a question of what I've done," she said as she filled our glasses again. "There are, um, pretty significant things about me you don't know yet."
"Well there are things about me that you don't know, too," I replied. "Did you know that I am NOT an Eagle Scout! How about that one?!"
She put her glass down and moved toward me, lying on top of me for the first time. We had never been this physical. She bent down and started to kiss me. "I trust you, Jakey," she whispered. "You should, Janice. I would never hurt you."
We embraced and kissed hard, my hands fumbling under her short sundress. She moaned as I kissed her neck and gently kneaded her breasts.
"Jake I need so much to know that I can trust you." She was more emphatic this time, looking me straight in the eye.
"You can trust me. You can."
I took off my shirt and tossed it into the speckled sunlight on the grass near our blanket. Her small hands moved slowly across my chest, to my neck. She raised her back from the blanket and pulled off her dress and unclasped her bra. Her nipples were standing out in anticipation, pink and beautiful. I wasted no time kissing them. giving full attention to their tiny, taut peaks.
As we kissed, she moved her hand down toward my groin and began to massage my full erection. I also moved my hands downward and felt her gasp, but she continued to massage me through my pants. Before we went any further, she gently moved my hands away. She slowly stood up and, facing away from me, slid her panties down her legs. As she turned around I saw what I hadn't suspected.
Without a word, I stood up and removed my jeans and boxers, joining her on the blanket. I resumed kissing her and she returned my passion one thousand fold. We were face to face on the blanket, our staves and scrotum mashed together.
"Oh, Jakey, I have to explain this, I know. I'm a pre-operative transsexual. They are going to make me into a woman in a few months. I've already scheduled..." she whispered.
"All I know is that I want you," I interrupted. "You are what I have come to desire. So you're under construction. Who isn't? This is a strange package, but life isn't neat and tidy."
"But it's so...strange for you. It has to be strange!"
"OK, it's strange, but it's not insurmountable. You have always been and always will be, to me, a woman. How you were born is, in a strange way, somewhat irrelevant, if that makes sense. I know who you are and who you want to be."
I laid her on her back kissing her neck and tummy. My body was raging with desire and erotic confusion, which only added to the passionate moments that followed. It was then that I was faced with a dizzying and awesome array of circumstances, questions. Do I take this rather large, thick penis into my mouth? It belongs to a woman, I mean a person, that will be a woman. I want to please her, but should I wait until after the operation? Is she gay, I mean, is she going to be non-gay? Is this going to make me gay? I mean, she WILL be a woman pretty soon. My mind was grabbing at straws. The situation was what it was: accept her for who she is today and who she will be in a few months, or don't.
She trusts me.
I kept thinking over and over about how difficult it must have been for her to come up here, to disrobe in front of me, baring her body for me to see. Showing me what she was by birth, not by choice. I also reflected on the past three months and how I wouldn't have traded a second we'd spent together. We were falling in love with each other. How long would it be before I could find her equal? Would I ever?
I gripped her shaft, hesitant at first, massaging it gently. My hesitation, my wanting, my confusion. What was happening? What am I? What are we? Who am I? Who are we, who are we together? I stopped thinking about it and slipped it into my mouth. She recoiled gently as I, for the first time, sucked the cock of another person. I had from time to time had fleeting homosexual thoughts, but nothing that could compare to this. I was giving her head and I was enjoying pleasing her. As I engulfed the shaft I gently rubbed her sack, feeling the testicles within, wondering what this would be like after the operation. I mean, what would they do with all this cock? It was at least six inches long, thick, totally out of proportion for her body. In fact, mine was probably only a few inches longer.
I continued giving her head as she motioned for me to move so that she could take me into her mouth. She wrapped around me like a warm, silken glove, her red lips bobbing all the way down to my scrotum. This was by far the best I had ever enjoyed, and it was difficult to remain focused on touching, sucking, licking her. I thought to myself that this was a rare opportunity to have such an experience. The contrast of her delicate, beautiful features, her tiny hands, her wispy hair, her gorgeous face. The contrast between those frail, feminine features and this stalk of flesh wedged into my mouth. I was in a state of total psychological and sexual overload. No prior experience could compare to this.
After several minutes of oral sex, I could feel her tensing in her abdomen, and her sucking becoming more rhythmic as I allowed her post to enter my mouth again and again. I was cast into another new experience as her semen trickled out of her and into my mouth, a creamy salty mixture. I never thought I would say this, but I enjoyed it. I kept sucking her until her peak subsided.
As I moved toward her face, her mouth agape with subsiding pleasure, we kissed sensuously, passionately. She was satiated and I was pleased at my ability to satisfy her.
I lay down next to her face to face as she caught her senses.
"It's been so long for me. You can't imagine how long it's been."
"My ex never knew. I dated him for over a year."
"Didn't you ever have sex?"
"I gave him oral and he used to have anal with me, but only in the dark. I am so relieved that my secret life is over. You made this possible, Jakey. I am so...I am so...I am so in love with you."
Again we locked into an embrace that seemed to last for hours. Her soft, supple, features relented to my touch, my moves. She was mine.
She kissed me full on the lips, her softening member pressing against my abdomen. She pulled me on top of her and lifted her legs high. She was so limber it was amazing. Reaching behind her she found lubricant and began to apply it to herself.
"Please tell me you like anal sex."
I didn't have to reply. I placed the thick tip of my straining member at her entrance and gently pushed inward. Her opening was extremely tight but after a minute or so of relaxation, I was inside her headfirst, followed by the remaining portion of my girth. I applied more lubricant to my shaft as it poked, plunged, and sawed in and out of her tight pink hole, my testicles relaxing and swinging hard against her bottom with each thrust. I continued to slide inside her, kissing her on the lips, kissing her tits, stroking her cock as my penis invaded her anal opening.
I don't know what it was that sent me over the edge. The delightfully tight anal sex, sucking her cock, her sucking mine. I began to stiffen and thicken inside her. Within seconds I was filling her with thick jets of cream as I licked her tits. As I was coming I noticed that her cock was semi-hard and she was masturbating. This was quite simply an all-out assault on the senses. In less than five minutes I was hard again and, after thoroughly cleaning myself off, was fellated to an incredible peak, dumping what little my straining glans had to offer into her mouth.
There were many, many questions to be asked and answered. But now was not the time. This was more than a sexual escapade. This was the beginning. This was the beginning of something more.
To Be Continued...