Janice Ch. 02

Story Info
The relationship takes an erotic turn.
1.7k words
4.42
77.4k
14

Part 2 of the 2 part series

Updated 10/18/2022
Created 06/09/2001
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Jakey
Jakey
92 Followers

We continued to date and were falling in love with each other. I had begun to come to terms with the physical differences, or rather similarities, that we shared knowing that in short order things would rebalance into normalcy. But the ensuing months would bring some confounding events for both of us, confusion and conflict that defied resolution.

Janice and I slipped into a comfortable rhythm of intimacy that was both erotic and satisfying. I accepted early on that she was in a state of transformation and was comfortable with the situation. More correctly, I secretly reveled in the knowledge that living this life was a rare and coveted treat. My so called girlfriend was well endowed and I had explored facets of existence of which most men only fantasize. All outward appearances were that I was dating an attractive woman. When we were in social settings people saw a happy couple, maybe man and wife some day. But appearances can be deceiving, and nothing could have been more diametrically opposed to what people thought we were: a loving heterosexual couple. We did love each other, but that's where their knowledge and supposition ended and our secret life began.

Her surgery was scheduled for late September, but it was in late July that things changed. Our intimacy up to that point had consisted primarily of us pleasuring each other with oral love. I admit that initially I was so in love with her that it was only peripherally important to me that she had been born as she was. But as time wore on, even knowing that her transformation was on the horizon, I began to wonder about myself. I loved our intimacy; I loved the feeling of her next to me, and did at times fantasize about when she would be changed and how that would affect us. I had assumed the male role exclusively until late July, and enjoyed our intimate encounters entering her and pleasuring her afterwards.

We had planned earlier in the week to clean out the dreaded garage on Saturday, so we got up early for a weekend day and got to work. By 3:00 we had finished our daunting task and agreed to get some iced tea and get cleaned up. Saturdays off for Janice were rare because of her job, so having her home all day was a terrific bonus. We went into the master bath and shared our oversized shower. Naturally, and typically, our thoughts turned to intimate encounters as the hot water cleansed away the day's toil and sweat. We sneaked out of the shower and quickly headed for our bed. In true form for any other couple, we had our "normal" things we did which was simultaneous oral pleasure. I had become more than accustomed to accepting her into my mouth I must admit.

And that's exactly the way this Saturday interlude began: lovely, warm and wonderful, side by side and planted firmly and gently opposite. Each motion was returned, two eager and willing souls with smiling eyes and lips curled around each other. Our eye contact over a span of months became an accurate and sensitive method of communication during our intimate encounters. Janice would raise her eyebrows when I did something just right, and would scrunch her brow when I thrust into her a little too hard. I'm sure I returned signals in kind, and she became an increasingly wonderful and attentive lover.

But that Saturday afternoon as we snaked our way through a wonderful albeit predictable pace, Janice had something else in mind. Without a word, she withdrew from my mouth and reached to the nightstand for a lubrication tube. She motioned me onto my stomach and, as if we had done this many times before, began to lubricate me. The only problem was that we had never done this before, never talked about it, and I certainly never thought it was going to happen.

"Janice. What are you doing?" I laughed through my words.

"I don't know, honey, I thought we'd spice things up a bit."

"OK." I rolled onto my side. "Baby, I thought that things were going, you know, like you're going to be undergoing some changes pretty soon."

"Yeah. I think I will. It's just such a big step that I want to make sure I don't make a mistake. I know we need to talk about it but you have to understand this from my perspective. I was born a man and until recently that's what I was. I just want to make absolutely sure that's not what I am. I want to make sure that the change is right because it's so permanent."

"What are you saying…exactly? Are you having second thoughts about the surgery?"

"I know I should have told you this sooner, but I have already put the surgery on hold. Honey I need to know that it's right for me."

I looked at her and just attempted to digest what was going on. I sat up and put my hands on her shoulders. As I looked her straight in the eye I began to share my thoughts and feelings with her.

"Janice, you definitely need to do what's right for you. You know how I feel about you, but you must be going through some very hard emotions right now."

"You've been supportive, honey, I just want to make the right choices. I've probably made the wrong ones, or at least some wrong ones, up to this point."

"Not wrong, baby doll. Different."

She flashed that priceless smile. "Will you do something for me?" she asked. "Let me do this. I need to know more about myself. Will you help me?"

I kissed her and submitted myself by lying face down and wiggling my legs wide. My arms were above my head and held tightly to the headboard frame pegs. I could feel my hands shaking as they gripped the cylinders, wondering what was going to happen. I could hear her rustling above me. My heart was beating out of my chest because I couldn't see what she was doing above and behind me. My submissive and vulnerable position totally exposed me to her self indulgent experiment of which I was a willing participant. It wasn't long before she made contact with me. Her girth and warmth surprised me, gently resting at my entrance as I had done to her dozens of times. It was so different being in this position, looking down at the sheet, wondering what was next. It was the uncertainty that was so unsettling actually. If she had laid out in detail what she was going to do to me, it probably would have been no great matter. The fact that I was being driven, my bottom raw and open, new, willing, but hesitant…this was the source of my trepidation and fear. I didn't know if she was going to be gentle or rough, fast or slow. I didn't know if I would be filled with her warm flow or if she would abruptly withdraw and spray the small of my back.

It was only now that I finally realized what every woman experiences at some point. Those futile rearward glances to determine the direction gain only glimpses into the mind of the man. Tightening and loosening your muscles, I eventually learned, only delays or accelerates the inevitable release. It was erotic, new, and in its own way deliciously different. Once again, it provided me with a chance to experience a fantasy, an opportunity to walk a path that I likely would never again traverse. With my lover, my love, it was a simple and straightforward choice.

As she managed herself inside me I made the requisite look back, replete with smile, as she eased deep into me, my first experience as such. The best word I can use to describe the deep pressure that I initially felt is "interesting". It neither hurt nor was pleasurable. I knew she was inside me, I could see her in the dresser mirror moving into and out of my body, but it was only exciting because of the knowledge of what was happening, not because of the event itself. I caught a glance of her with her hands on my bottom, spreading me wide. In the past few minutes I didn't even notice that she had succeeded in gathering me at the waist, turning me into a perfect triangle with the bed. She was up on one knee to provide her with an optimal penetration angle.

I could hear her moaning louder as my body provided her with increasing resistance to her motion. She became increasingly aroused and I easily noticed that her thickness increased substantially. In the past few months I became very good at knowing when she was approaching climax based on the diameter of her penis. I thought to myself, at this point if she were in my mouth, I would be sucking her all the way down and resting with my lips at the base of her shaft, hands massaging her scrotum. But, alas, she was lodged deep into my only other opening.

In the mirror I could see her mouth open as she approached her peak. For some reason, ostensibly her pleasure, she decided to withdraw completely and poke her head plus about an inch into me in quick thrusts. After 14 rather painful extractions and insertions (that is an exactly count incidentally) she lodged a bit deeper and I felt her pulse inside. Sensations washed over and inside me as I remained with my body totally exposed, deeply penetrated, and now filled with semen. It was a strange and wonderful experience. She kissed the back of my neck and withdrew from inside me. Immediately I was in mild discomfort, primarily a burning sensation, as my opening returned to its resting position. The nerve endings on my opening were rubbed and stretched raw from her little pre-orgasmic playtime with entering and exiting my body. Despite the rather copious amounts of lubrication she applied, my body had never been used and/or abused in such fashion, so it goes without saying that the remainder of the afternoon and evening were uncomfortable.

"Oh, baby, I am so glad we did this" she said.

I thought to myself, yeah I guess I've been elated when I've captained my ship over someone's bottom. I thought to myself and replied, "I am, too. I know you needed to do this, baby."

Actually, I wasn't all that glad. I was burning and spent and beginning to wonder if I had made the biggest mistake of my life.

Jakey
Jakey
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8 Comments
Rapier875Rapier875about 1 year ago

You've written more chance this so why didn't you finish it ?

So frustrating.

MrBill36MrBill36about 9 years ago
Interesting Outcome

I met a transvestite in a Bar in SanDiego and as things worked out, we ended up in her hotel room. She serviced me first orally and allowed me to perform my first anal penetration. We rested, then she convinced me to allow her to also penetrate me annaly. The experience was not what I had expected, not painfull and ended up being quite acceptable. When she ejaculated into my rectum, I could definitely feel the fullness and I found myself actually expanding and contracting my anal muscles to help her complete her ejaculation - not at all painfull. I did have a very strong feeling of needing to find a toilet to "discharge my gift" soon following the experience.

AnonymousAnonymousabout 10 years ago
more

Would love to hear more please !

Marcie4youMarcie4youover 10 years ago

Anxious to find out what's next?

AnonymousAnonymousabout 12 years ago

Great story.Would love to hear more

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READ MORE OF THIS SERIES

Janice Previous Part
Janice Series Info

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