Jack & Jill - his first time with a transexual

Jack and Jill meet

It was when I went to the patio to enjoy a cigar after dinner that we met.

On the road for business, I found a decent bar and grill near my hotel where I was welcome to enjoy a fine smoke. I had dinner and then moved outside for a relaxing smoke in the cool weather. I lighted a Churchill-sized stick and after a few minutes of solitude, an exotic looking brunette spoke from just behind and to the side of me.

“I love the smell of a fine cigar,” she said in a sultry voice that got my attention.

I turned to look as she moved forward into my view and was pleased to see a young woman dressed in a red formfitting top with a leather mid-thigh skirt, and more importantly, luxurious long dark hair as straight as if ironed.

“You’re welcome to enjoy one for yourself if you wish,” I said while politely standing to greet her. “I’m Jack,’ I added as I extended my hand to take hers lightly.

“Jill,” she said with a smile and laugh.

“No kidding, Jack and Jill?” I questioned.

We both had a short laugh and I motioned for her to sit across from me. When she sat down I got a great look at a long pair of tan legs and was impressed with the slight curve of her hips, slender torso, and just right sized breasts.

Now I was looking at her, face level with mine, and saw her dark eyes and lusciously thick lashes. She was exotic in that she was part Asian, possibly part Anglo and almost had a look of a Latina as well.

It is quite sexy to when a hot chick smokes a large sized cigar. Clearly it’s the oral phallus action but, there is also a sexy confidence to such a woman that I find attractive.

Jill allowed me to light the cigar as she expertly turned it, keeping it far off of the flame demonstrating that she was not new to the delights of a fine cigar. I was already hoping she was not new to other oral delights as well!

We visited for some time and she was obviously inserting and removing her cigar in as sexy a manner as you could imagine. It would have taken nothing more than her walking up to me to get me excited and thinking about sex with her. Add the sexy smoking, with the good conversation, and this became a pursuit I could not refuse.

After I thought I’d enjoyed about as much as I could take, Jill began blowing smoke rings! Wow! Putting her full lips in that rounded, puckered position needed to blow the rings was more than suggestive, it was almost pornographic.

By this time she knew I was staying in the hotel next door and much about where I was from and what I did for work. I had tried to get her to talk more about herself but she would say little except that she worked in show business.

One thing that I kept wondering about was if at some moment she was going to tell me she was for hire. It’s not unusual to have attractive women strike up conversations when smoking a cigar – you get everything from how the smell reminds them of their fathers to how they enjoy smoking too, as if it is the greatest novelty in the world. But few are as sexually suggestive as was Jill.

I’d already eaten dinner so it wasn’t a great idea to ask Jill to dine. Instead I decided to blurt out: “Jill, how about spending the rest of the evening with me at my hotel?”

“I can tell you’re ‘up’ for it,” she replied confidently while glancing through the metal screened tabletop toward my crotch and smiling.

“Let’s go,” I said as I stood up and offered her my hand.

While taking my hand and pulling herself up, Jill said: “Jack, I don’t want you to get the wrong idea. I spoke to you because I was looking for company in enjoying a cigar. But after talking with you I felt a real spark,” she said. “I’m not a slut and don’t go around meeting guys and going off with them as a regular behavior. In fact, it’s really tough for me to meet and spend time with most men.”

“I can’t imagine that, as gorgeous as you are. Plus you are a great conversationalist,” I replied.

“I’m a bit different,” she said as she pressed my hand and stopped walking for a moment. “I don’t have any medical problems or anything but, I have a situation that can sometimes be a bit of an embarrassment.”

I pulled her hand and started us walking across the parking area toward my hotel again.

“I’m sure I can deal with it Jill, whatever it is,” I said confidently while pulling her along.

“Just be gentle with me, please,” Jill said in a pleading sort of manner as we walked.

“I promise,” I told her, meaning it.

---

We had held hands up the elevator and down the hallway to my room. Our body heat and flushing cheeks that told the entire story of our attraction.

After we entered my mini-suite and walked just as far as the small couch, I felt Jill’s hand on my ass and we turned into a passionate kiss. Our tongues lashed as each other and we were filled with the exhilaration of hot lust being fueled by tasting the first morsels of what would become a banquet of sex.

As we groped and rubbed our bodies together and began to explore with our hands, we fell lightly to the sofa without parting our mouths. I was enchanted with Jill’s olive, smooth skin and sensual looks and even more delighted to find her wearing high quality, lacy lingerie under her blouse.

Her small breasts were swollen and encased in a front-clasp bra through which her hard nipples could be seen as they pressed hard against the feminine fabric. I had much practice with this type of fastener and easily liberated her breasts in one quick, one-handed move.

As I kissed my way down her slender neck, Jill was moaning and breathing harder. When I brushed my hot tongue across her nipples, her back arched and she pressed her chest toward my mouth for more.

While I bathed her nipples with my tongue my hands began working around to her hips and lower back. I began to unbutton and unzip her leather skirt and she assisted by moving in just the right way.

“Jack,” she said breathlessly. “Please promise me again that you’ll be gentle.”

It sounded as if she was imploring me not to hurt her making me think that possible she could be a virgin. I didn’t mind and it wouldn’t be my first time but, I found it hard to believe given our ages and her overall sexual confidence.

While nibbling on her breasts and stomach, I pulled her skirt down as she lifted herself to allow it to pass. She pulled the one leg up and through it that was hanging over the edge giving me full access to her body.

Again, her panties were of the highest quality and very feminine, something that is important to me and adds greatly to my enjoyment.

I began kissing my way down to her pussy and when my mouth began to press against the fabric where her wet slit and clit should be, I felt heat but not the expected wetness and musk.

Moving back just slightly so that I could see the area more clearly, I was more than surprised to see what seemed to be a smallish, maybe five inch, cock pulled back between her lovely thighs.

In my surprise, I looked up at her gorgeous face and saw the most beautiful but fearful expression. Again, before I could speak, she said: “Please, please be gentle with me.”

I was no stranger to what a shemale or transsexual was. I had fantasized about being with one before and looked at pictures and movies online. But I’d never acted on such a desire nor had it been a major interest.

At that moment, while looking at her lovely expression, I made a decision. I directed my gaze back toward her boy clit, pulled the crotch of the panties back so that there was more room, reached in and moved her cock up and forward, and then began kissing it as if it were the most sensual clitoris I’d every touched.

As I did this, Jill relaxed and began running her fingers through my hair and pulling me closer to her boy clit. As she did, I moved the panties to the side and did something I thought I’d likely never do. I took a cock into my mouth and smothered it with saliva while running my tongue around and around its full width.

“Oh, Jack. It feels so wonderful,” she began to say repeatedly as she pressed my head lightly.

I just sucked and sucked, moving my head up and down and working my tongue over the sensitive areas of her boy clit. As she began to lift her hips up thrusting her cockette into my mouth, I slid my hands under her ass and squeezed in rhythm.

It wasn’t long before she began to tremble and I felt what was coming. Another decision to reach and I chose to keep her in my mouth through full orgasm.

Her thrusting stopped with her hips pressing up against me and the pressure from her hands on my head become stronger. Then her clitty erupted in my mouth. Hot spurt, after hot spurt filled my oral cavity while she held me in place.

Soon Jill relaxed back down pulling her clit from inside my mouth. She then began pulling my head up to hers and kissing me, taking her own spunk from my mouth and swallowing it. Wow! That was sexy. I didn’t mind taking in my mouth but I wasn’t up to swallowing on this my first time. Her action relaxed me and we then kissed slowly as we enjoyed the feeling of the natural lubricant on our lips and in our mouths.

During this time, Jill’s hands had found their way to my crotch, unzipped my trousers, and had started to fondle my hard, wet cock.

Suddenly she pushed me back, crawled to the floor, and planted herself on her knees right in front of me. As she locked on my eyes with her dark oriental eyes, she lowered her mouth onto my cock and began giving me the most intense blowjob I’d ever experienced.

Just like Jill, it did not take long before I gushed into her mouth. And, unlike me, she swallowed it all as if she loved it.

She didn’t get up to kiss this time though. Jill stayed between my legs and licked my cock gently, careful not to over stimulate but directly enough keep it from going completely soft.

I just looked at this lovely woman between my legs and did everything I could to burn this sexy image into my memory to last a lifetime. She was more beautiful, feminine and sexy than ninety percent of the women I’d ever met, much less those I’d made love with. And, she was making love to my cock and my balls in a way that no other woman had ever come close to.

“That was incredible,” I said to Jill as she was licking my balls and working me back to full tumescence. “And what you’re doing now feels like heaven.”

“Mmmm”, she said looking at me while taking my cock back in her mouth and deep throating me.

It was a new and fantastic experience to feel my cock enter the top of her throat; I could feel the vibrations in my cock head when she moaned.

After a few more minutes of getting me back to life, Jill came back up on the couch and began licking and kissing my ear and neck.

“Jack, I want to feel you inside me,” she whispered in my ear between nibbles. “I want your big cock in my ass.”

As she was saying this and nibbling on my ear, her hand was gripping my cock strongly keeping it at full attention.

“I’d love to fuck your lovely pussy,” I said and began to pivot my body so that I could stand.

I stood and removed the rest of my clothes with Jill’s help and we moved to the bed which had already been turned down by housekeeping.

On the way, Jill had grabbed some KY from her purse and I began to apply it to her very sexy, smooth, boy pussy.

After some time of lubing her and my cock, she rolled onto her back and pulled her legs high in the air giving me full access. I placed two pillows under her lower back and then moved in on my knees with my cock pointed straight toward her boy pussy.

“Please Jack, please fuck me,” she said with anticipation. “Put your manly cock in my pussy-ass.”

“Jill, I’m going to fuck you with my hard cock sweetheart,” I said as I pressed it against her relaxed opening.

Looking down at her lovely breasts, gorgeous face, and long dark hair fanned out on the bed, I couldn’t believe that she had a cock and no other sign of masculinity. No Adam’s apple, no think torso or arms, just all feminine woman with a very smooth and nice looking cock.

“Fuck me Jack,” she said as a command.

I pushed into her ready ass and entered her sensual body. Deeper and deeper I pushed, slowly and deliberately as her eyes rolled back and closed while her lips parted and mouth gaped open at the sensation.

I held her legs tightly against me with her ankles on my shoulders. Then I began a slow in and out thrusting rhythm that grew and grew until I was fucking her with full vigor and speed.

“That it, Jack. Don’t stop. Fuck me, fuck me, Jack,” she said with repetition.

“I’m fucking you Jill,” I said as I moved faster and harder into her ass holding her legs ever tighter. “I’m fucking you, you beautiful girl. Feel my cock pulsing in your tight pussy. Feel it!”

I began to order her to enjoy the fucking she was getting and the more I talked the more she thrashed around on the bed. One hand was pinching her nipples and the other was thrown up and behind her grasping the headboard railing.

“Jill, I’m going to shoot into you!” I exclaimed.

“Yes, yes,” she panted. “Shoot your come in my pussy. Please, shoot it deep inside me.”

“I’m going to fill you with my come,” I said loudly just as I began to seize. I plunged as deep as possible and enjoyed the massive orgasm as my both my muscles and hers pulsated. The feeling of her tight hole gripping and pulsating on my cock intensified the orgasm beyond belief.

Soon we both began to relax and Jill’s legs lowered to the bed as I pulled out of her tight ass.

I crawled up beside her and kissed her as I stroked her now very hard cockette with my hand.

“You are so incredible,” I told her. “Let me take your come again.”

She nodded yes and I moved my mouth to her cock and began, for the second time ever, sucking a penis. But this was no hairy boy dick; this was a feminine, smooth, attractive large clit. And I sucked her and squeezed her small balls until she again shot her load into my mouth. This time, I swallowed her seed.

Jill and I took a long shower together after that, slept for a while, and made love again a few hours later. This time, I told her of my love of ass play and stimulation and asked her if she would be willing to fuck me.

“Jack, I’d love to fuck you,” she said excitedly. “I’d love to fuck you more than anything I’ve ever done in my life.”

Jill rimmed my ass with her tongue, which was a tremendous feeling, then lubed me up good. And, since I often use a small dildo on myself when alone, I was ready to accept her thin cockette immediately.

“Get on all fours, baby,” she said.

When I did, Jill came behind me and pressed the head of her cock against me and the feeling was indescribable. The feeling of her cock was much better than from a plastic phallus. As she pushed into me, what I noticed most was the heat.

“Oh baby,” I said with my head buried in a pillow and my ass sticking up in the air taking her cock. “It feels so good.”

Slowly Jill began to fuck me, a feeling I had never been able to attain while just holding a dildo in my ass. It was fantastic as she slid in and out. I could feel sensations I had never before noticed.

“Jack, your ass is mine,” she said playfully as she began to fuck me faster and harder.

“Yeah, baby,” I replied. “fuck me hard. Make me your plaything.”

Her cockette moved in and out of me faster and faster and when she reached around and grabbed my swollen cock, I thought I would explode from pleasure. But, before I exploded Jill shouted: “Here it comes baby, here comes my pussy juice!”

And with that, she shot a hot load deep into my bowels. The feeling of the hot liquid entering me was unmatched by anything I’d ever felt. And just as she came, she squeezed my cock causing to erupt for a third time. As I shot my load, each spasm clamped down on her cockette in my ass and milked every bit of her sweet juice from her boy clitty.

After our bodies relaxed, we lay next to each other and kissed and stroked each other for a long period of time.

Finally, I asked: “Sweetheart, you never have told me what you do except that you are in show business, what kind of show business?”

“I bet you think I must be a stripper or something,” Jill said coyly. “Well, I’m not. I own the local art house movie theater. And what’s more, there’s not a person in this town that knows my little secret – except you.”

“Well Jill, if you don’t mind,” I said, “I’d like to keep it that way but with one condition.”

“What’s that?” she asked.

“That they all do get to know that I’m your man,” I answered.

She just smiled and kissed me deeply and lovingly.

“I think we might arrange that,” she said.