I almost felt like I was being stood up, and it took the wind out of my sails. I was getting up to leave, rather embarrassed that she hadn’t arrived when her 4th text came in.
“I’m here, but I can’t find anywhere to park.”
I was aggravated and felt let down by having to wait so long for her to come, but I sat back down, calmed myself down, and waited. Just minutes later I saw her walking across the dining room floor, towards the table. I got up and hugged her and she must have apologized 10 times for being late. Event that sarcastic ass waiter – whose tip reflected his condescending mouth – came over and said; “Oh, you finally made it.”
I was as nervous as could be because now I wasn’t just texting a man, who was transitioning over to a woman. I was sitting in public with her. Now in the light of this room, for the length of time we were together sitting face-to-face, I could truly see more “manly” features on her face and hands. Anyone else who looked could see as well. I was still interested in seeing where this could go, but there was no denying, she wasn’t a she. I think we were both very nervous throughout the dinner, but we made conversation and made it through without it becoming too awkward. When we finished, I walked out to her car, got a hug, and promised to chat more throughout the week. I’ll spare you the lengthy detail of our conversation, because this story would be ten more pages, so on to the second date.
The second date was a bit better. She wanted Thai food, so I met her at the restaurant she chose. I think the nervousness was less intense than it had been before, but we were still a bit uneasy about being alone together. I know it was for me. Even though I wanted to date a shemale and experience dick again. There was no doubt looking at her from across the table, I could still tell it was a man’s face. A man’s neck. A man’s arms, with hands as big as mine. Even if she could pass herself off as being a woman at work with elderly patients who couldn’t see her distinct features. I could. And I guess at the time it mattered. But, it didn’t. Our second date ended similarly, I walked her to her car, but this time after the hug, I got a small kiss on my cheek, but it went no further.
I know you must be asking yourselves if you could tell and it bothered you, why did you continue to see her? Well….
I thought she was beautiful. Even though she wasn’t born a female, she did an excellent job trying to be one. She had deep brown eyes and was always trying to speak in a feminine voice. Jillian seemed very personable, very caring, very honest, and didn’t appear to be playing the field. And through it all, she was very open about her transition. In the dark recesses of my mind, dating a “man” scared me. But it also excited me. I wanted to see a real dick again. I was fascinated by shemales. I wanted to give head again. I wanted to be fucked. I wanted to fuck her. I knew what I was getting into. This wasn’t going to be some deep make-out session where I’d be surprised when I discovered her dick. I ran it through my head feverishly. Tits or not. Long hair or not. Painted fingernails or not. Women’s clothing or not, there was still a dick between those legs. Albeit a dick I wanted to see, but, a dick nonetheless, and if I had my chance, I was going to find out if it’s what I wanted in life.
Many nights of polar thought swings. On one hand, I thought, I wanted that dick. I wanted to see it and suck it. I wanted to know what it was like in this type of relationship. But would I be ready enough to continue dating and then become very open and honest with friends and family? On the opposite end of that; I would be dating a man! And if it developed into a relationship, then it wouldn’t be a fling or some one-night stand. I would be sucking dick every time we made love. That was scary. Moreover, how would my friends and family react to that? All questions that time would have to solve.
But our conversations that night and following text communications with her developed into deeper, more meaningful, evolving interests and I just kept going for it.
Our third date was ice cream and miniature golf. It was so much fun. We met later than usual and went to one of the recreational parks LA has to offer. We sat and ate some ice cream on the park bench just outside the golfing area. We had such a great time talking and just being out in the cooler evening air. She was wearing a light, free-flowing knee-length dress, that had shoulder straps. Her tits were bulging under the material because the top was tighter than the bottom. We went into the golf park and played 18 holes of mini-golf and even though I could tell she was a man; I was actually more relieved being out with her that night than I ever had before. We laughed, we giggled, we hugged, we cheered each other on. But, at times, we tried to make each other miss the putt, on the putting green. It was so enjoyable. By the time we left, it was pitch dark and she had parked closer to the entrance than I had.
Jillian offered me a ride to my car and I accepted. She drove across the parking lot to where I parked my car, backed in, rolled down the windows, and shut the car off. We were just sitting there talking and laughing about the shitty game we both had just played when she started telling me about a crazy patient they deal with frequently and before her story was over, we were both laughing so hard, we were crying. I placed my hand on top of hers as she rested her arm on the armrest and I cupped her fingers inside of mine.
report We both caught our breath after her story and were just leaning back in the seats, taking in the salty LA air. I angled myself more towards her leaning on my left hip, and she turned to face me. I knew we were going to have our first kiss, but I didn’t know who was going to make the first move.
“Jillian,” I spoke. “This was so much fun. I’m glad we got together again.”
She smiled at me and said, “Yes Tim. It was.”
I leaned in to kiss her and our lips touched. I could feel her trembling as much as I was and I knew we were both extremely nervous about this. But as our lips parted and our tongues met, I could feel the warmth of her mouth as the kiss deepened. Now I had never kissed a man, let alone kissed one while transitioning, but I will tell you my heart was racing.
We held that deep kiss for about a minute, just getting used to how one another kissed, and finally finding that groove that worked. When I pulled away, she smiled at me, still holding my hand, and spoke, “That was wonderful.”
I thought it would be the end of it and I would get on my way, but she reached her left hand out and placed it on my arm, which was still holding her right hand, and looked me deep in my eyes. We didn’t speak a word, we just sat there in the darkness, with the bright neon lights that lit up the golf park, until I leaned in again.
This time any fear or apprehension of kissing her was subsiding. Her left hand came to rest on the side of my face as our kissing grew deeper and our hormones were awoken. I felt myself getting hard in my pants as much as you might think I was taken aback kissing a man. I was rather excited.