Watching Jenna Ch. 04

Cathy saw my muddle, "Will you at least consider the request Keith?"

I then quickly realized that there was still something attracting me to Michaela and I wanted to find out whether she and I could become something.

Cathy reached across the table and took my hand as I blurted out, "When do you see this happening?"

There was of course selfishness in my suggestion but I had not pushed this to happen. Michaela's gender conditions now seemed unimportant especially after the past weekend with my sister.

"Well, really Keith, I would assume anytime Keith."

I looked away and considered my needs and whether there was a spark, Leyna had seen something. When I looked back Cathy had wiped her face and she saw my resolution.

"So you will meet her? I meant to say, you will come over, you know?" she asked.

I looked at Cathy and thought about what I was actually suggesting.

"No, it has to be a date. Only then does my head see this clearly Cathy."

She squeezed my hand, "Just be yourself Keith."

I wondered if she even knew I had desired her girlfriend these past few weeks. Maybe Cathy had forgotten how I had first met Michaela. No, she just was trying to help. My head had crashed hearing the erotic story from Cathy and something crazy was stirring in me about Michaela.

Scene Eighteen

My sister wouldn't understand the context so I didn't call her for a few days. On Friday morning Michaela sent me a simple text :

' our date could be tonight Keith '

So I arrange a table and the car service and I called her.

"Let me take you to dinner Michaela," it was that simple. I cleared my desk early and headed home to tidy up and chill the champagne.

An odd realization came to me as I got ready. She was just a girl that I liked a lot and therefore I was going to, well I would attempt to seduce her. She already liked me and she had created the opportunity for this date. But wasn't it more of a liaison? Maybe I was hoping for something more than what it actually was, an affair. Her lover had asked me to sleep with Michaela and I had agreed. Now, tonight, I wanted to find out if there was a way that Michaela and I might have a relationship. I wasn't thinking of Cathy now.

I recalled the difficult conversation with Cathy two days ago; I had been hard the entire time. The date was really just a shag; I was going to somehow 'complete' Michaela's sexuality.

I stopped that thought as I shaved. I wanted to be with her but this confounded me. I had to remember what Leyna had told me, how she was a woman and therefore so was Michaela. Even if what she wanted was to be deflowered I hoped to be her lover. This act wasn't to sully her for it would be with her consent. I recalled the last time, just four days ago, that I had dreamed of Michaela. That was before Cathy had shared her story and the request.

As I finished my shave I knew I would be okay sleeping with Michaela. I was semi-hard as I re-focused on my hair.

Michaela had insisted that Tony would drop her at the restaurant and when I arrived I saw Tony's car pulling away. I saw the beauty walking toward me and smiled.

Michaela kissed my cheek, "She was a bit of a security blanket Keith. I'm looking forward to this. The kitchen does great seafood."

I felt better sensing her nervousness. It matched my own. Michaela was dressed in a sexy dress with naked legs and heels. Her nails were colored a soft blue which matched her eyes. Her hair was an updo with a purposeful messy twin braid. The dress looked expensive, silk with a translucent buff color but her shoulders were bare; no bra and then I saw her slightly protruding nipples. I got slightly stiff thinking how sexy she was.

She again kissed my cheek as I pulled her in close for a hug, "Wow Keith, we're finally going to do this, I mean our date of course."

Her breathe even excited me and her scent was musky but with a hint of vanilla.

"You look so good, and the perfume is," I asked.

"Tocca's Colette," she smiled.

I had read a translation of Colette's story collection the "Vines of the Vine" in a college seminar on women authors. Now Michaela was in my arms and we would be together without the others.

I asked her if we should sit in the bar or take our reserved table.

"The bar sounds loud. Let's sit at the table now so we can talk Keith."

After we had ordered our dinner the Chardonnay arrived and we talked quietly as the setting sun fell across the marshland to the southwest. She told me of her acceptance at the College and her intention to study Literature.

"It may not be as practical as a profession but I have always wanted to write."

Michaela talked of her home without mentioning the bad issues. She spoke of her goals and desires to complete at least a degree at the College. I just listened and looked across at her. I enjoyed her beauty and her expressions. Though she was with me tonight I saw the pearl choker she had received from Cathy.

The meal was good and the shared wine was just right. After dinner we walked to the terrace as the Moon was near the horizon. She looked at me and we kissed.

"I'll call the car okay?" I asked.

She turned and simply smiled.

Ten minutes later we were at the apartment door and we kissed as she wrapped her arms about me. My hands held her bottom through the thin silky material of her dress as our tongues explored each other. We slowly realized that we needed to be inside, in bed, together and I fumbled with the door key.

"Please don't turn on the lights Keith, I want to undress for you right here with the moon glow from that large window."

I sat on the edge of the sofa arm as she reached to release her garment. It fell to the floor as I looked at her perfect moonlit breasts. She reached up to her nipples and pinched herself as she smiled at me. She didn't remove her panty nor her heels.

"Now you please," she said softly.

I stood and removed my jacket as she step closer. I then untied my tie and started to release the shirt buttons.

As she moved closer she asked, "May I do those Keith?"

She stood but was barely at my nose wearing her heels. Except for her panty she was naked. Michaela kissed me lightly as she finished with the shirt but left it open as she moved her hand across my chest, "Ummm, you are smooth,"

Then her fingers went lower and the belt fell with a soft bang.

"I want to fellate you first Keith. A warm cock is what I want now okay?"

I just smiled as she slipped to her knees and reached to pull my boxers lower. I looked into her eyes as she touched my stiff penis that first time. How I hoped this would go on forever. She was so beautiful and sensual as her tongue reached the tip of my penis.

"Yes Michaela," I finally said. "That is what I have wanted you to do all these past weeks."

As she played her tongue up and down my shaft I noticed her pearl earrings. Her eyes transfixed me as she continued to lick me and yet she would look up to my face. Her hand moved along my soft but erect dick as her lips covered me completely. I had never been sucked off like this. She seemed quite practiced at this for someone not accustomed to men but I just enjoyed her attention as her soft lips played with me. Each time she took me into her mouth deeply I marveled at the feeling at the entry of her throat.

"Oh damn Michaela, your mouth feels so good, oh,"

She smiled as her finger lightly played up and down the shaft as her tongue licked about the head of my cock. This was extraordinary and I wondered how, somewhere she had been practicing this.

"Oh, god, I'm so close Michaela, I'm going to,"

She reached up and her long finger shushed me. I moment later I erupted and flooded her mouth as she pumped my slippery shaft with her hands. I leaned back as she played her tongue across the head of my still hard penis.

Looking down at her smiling face I was about to speak but again she silenced me with a finger to her lips.

"Practicing has helped me Keith, and Cathy introduced me to a friend named Jenna but your hot dick is the best thing I have ever put between my lips," she said quietly.

I smirked but didn't mention Leyna's discussion. I just looked at this beauty. I didn't see her penis for the throng was still about her hips. Helping her up we hugged each other as my mouth found hers. Over her shoulder I saw that I had failed to shut the door.

"We were a little distracted huh?" she said.

I moved to close the door as she came behind me and we kissed as the door shut.

"Now I want to see you naked Michaela, okay?"

She giggled and turned to skip in her heels to the bedroom, "Wow, you do huh? Maybe when we get to the bed."

I watched as she stopped and bent at the waist and rolled her sexy bottom at me with her hands on her knees. The thin fabric disappeared between her tight cheeks. Then I saw her resemblance to that Jenna chick, skinny but wide enough hips and a smooth backside.

"Do you want to play with my tight hole Keith?" I stood several feet back watching her.

She looked at me and gave me a come here motion, "Lets get to your bed Keith. I want your body to fill me please."

I walked to where she was as she stood and took her hand, "The moonlight is perfect," she said as she seized hold of my penis.

"It seems that you still want me Keith," Michaela whispered as we slipped onto the bed and my seduction began.

I wanted to fill her but also to show how she was more to me than just tonight's main event. I had enjoyed our dinner conversation and had just stared across the table. She was beautiful and intelligent even though she felt she was less; she wanted to educate herself. I was certain the degree was in her future.

She had told me of the reading list she had prepared and I found her views on the economy to be clear and informed. Her work life didn't include a need to be aware of the larger nature of retail competition but she was leading our discussion on the tax disadvantages of the latest election.

"I have a subscription to the "Economy" and read it cover to cover. Soon I hope to travel to London," Cathy had suggested the magazine would help her understand the views beyond our borders.

As I lay near Michaela she was on her tummy with her chin on her elbows. Her breasts hung in that position and mesmerized me. I shifted near and we kissed.

"You know Keith, you do like me a little bit," her hand had moved to my cock and she held me as our intense moment neared. She had not removed her thong.

"Can I climb above you Keith? I would love to slip onto you like that," I kissed her just as she rolled and allowed her to straddle my waist as she moved the slim fabric to the side and my dick kissed her ass.

She bent to kiss me again and said, "I think I'm ready," but I considered the need for lube.

She saw my concern, "No Keith, I am okay," as her fingers reached to position her body's opening. I wondered but I felt the ooze of my semen as she moved my dick back and forth over her hole.

"Look at me Keith," and she slipped down atop the tip of my hardness, "Oh yes god, ohhh, yes," she moaned looking at me intently.

But then she smiled and reached around to hold my dick as she looked down at me on my back. She was quite still with her hips high but my cock tip inside the tight rim of her ass.

"Stay here, just so Keith, stay still with me," she breathed rapidly as she closed her eyes, "Stay there honey," I could only reach to kiss her nose but then she moved and ravaged my mouth.

"This is so perfect, perched atop you Keith," then she slowly lower herself, "Oh, oh yes, yes, honey, yes! Oh sweet god, you are inside me. Your warm prick is, oh oh, oh Keith,"

I held her as her breasts moved across my chest and her hand was on my hip, controlling the penetration.

"Yes lover, please fuck me," she whispered as I held us together with my dick deep inside her bottom. She kissed me and pushed her tongue into my mouth.

"But slowly Kei, Keith, the heat in me is incredible. My tight ring,"

She squeezed me with her body and I thought I might shoot off.

"Oh no," she saw my worried look, "You need to just move back and forth in my tight snatch honey. Yes, like that, wow, so good."

My hands came to support her bottom as her one leg shifted to her knee and together we slowly fucked each other. Her mouth and tongue never leaving mine. I heard one of her heels fall to the floor.

"Keith, is it possible?" she was now panting and I saw the flushed skin of her face.

"I'm coming? From your cock? Oh god I knew it was possible; god fuck me, oh damn, you feel perfect. Fuck me a bit faster Keith. Oh, fuck yes,"

I looked into her eyes as she bit her lip and her other hand came around my shoulder. She rode up and down on me.

"Ahh, ahhh, yes, like that," but her eyes were shut as she began to moan. The sound was soft and I increased my thrusts into her body as I felt my own release coming. Her tight ass, hot about my cock was going to be filled. My own breathing was sharp now as I lifted her up as we rolled to her back.

"Michaela I love fucking you," I screamed as her nails dug into my back and our mouths loved each other.

She seemed to go still and her fingers relaxed and released my skin and she began to shake, "Oh yes Keith, ohhh!"

Her bottom received the jets of semen of my orgasm but I slipped out of her body with my final thrusts.

"Oh god yes Michaela, I've fuc, fuck, fucked you!" I was gasping strongly.

The gooey cum shot onto her belly as I fell to her and my mouth again found hers. Somehow my dick found her hole and I slid into her again. We stay like this for several moments kissing.

As we rested I rolled to my back. We held hands but Michaela bounced up onto her knees.

"I want to eat you up lover," as she bent to lick my tummy clean.

I was flaccid but she smiled and moved her hips atop mine and sat on me. I lay with my eyes closed as her warmth and subtle attention caused me to stiffen slightly.

"I want you again Keith but let me continue this," she whispered as her hips rolled atop my softness.

"You have treated me like a Lady Keith," she said as I became slowly hard and she reached behind to allow the easy penetration.

"Your are so slippery now Michaela. Wow!" I said.

She didn't speak and in the dim light I saw that her face was content and her eyes were closed. She used her warm hole just as a woman would to milk my dick and after a few minutes she was bouncing off of my hips as my penis move in and out of her body.

She reached around to keep me from leaving her canal as her movement overcame me. My dick was on fire as she clamped down to squeeze me.

Now with her eyes open and her right hand playing with her breasts she said, "This is so much more than her toys Keith. I could get used to fucking you."

I pulled her into the kiss that I hoped would let Michaela know I wanted her more now than yesterday. I wanted to be her sole lover but I felt it should not be said.

"Oh god Keith fuck my ass, fuck me big boy, fuck me like a slut!"

The cream I shot was still enough to fill her. Afterward she lay atop my chest and we slept as it oozed to cover us. I held her as she snored softly.

Near morning I felt her get out of bed and she kissed me lightly after dressing. I heard the door closed and I got up noticing her absence. I walked to the large window naked to see her get into Cathy's BMW as they drove away.

I knew she had enjoyed the sex but her calling herself a 'slut' had told me I wasn't the one. I was just the first. She would need time. She might need me again and soon but for now Cathy could keep her sated.

I went to pee and saw the note on the mirror, ' Keith, I love your cock but Cathy 2 '

I awoke late on Saturday to find a thank-you note on my E-Mail from Cathy.

' she told me she loved being with you but now knew I was for her '

I heard the following week from Tony that Michaela, who was unaware of Tony's budding romance with Leyna, had agreed to marry Cathy. My heart sank but I was also happy for her. Tony didn't pick up on my disappointment and I wondered if I had been stupid to think Michaela was interested in me romantically.

"Michaela mentioned that she had had a liaison with a man and she became convince afterward that she was into women. She said somehow a penis just 'tangled up relations' whatever that means."

I wondered if Michaela had withheld our meeting, our 'date'.

The following week Cathy called me to assure me that her lover's affair was just between us. I got the feeling she was happy that it had been me to help settle Michaela and not a stranger. When I next saw Leyna she obviously had some word for she pressed me about Michaela. I told her of the date and their marriage plans.

"I just knew you could help her Keith," so it might have been my sister who had kindled the notion with Michaela?

Scene Nineteen

That Saturday Leyna had invited Tony as well as Florence, Jamey and Celone to stop by the apartment. I had considered telling Leyna of the sex play the three had had with Michaela but it was only hearsay. I hadn't discussed the Celone affair with her.

"Tony would be spending the night with us, okay Keith?"

Leyna had agreed to withhold my date with Michaela from Tony and the others. Again I was the sole man with these five women. Leyna had prepared several appetizers and I had made the chilled margarita cocktails. During the evening we learned that the following week Jamey would be in surgery.

"The size is important right Keith?" Tony asked me as we enjoy the second round.

I told the girls that I was into smaller breasts but Tony didn't believe me.

She pushed, "Whose are the right size then Keith?" and the five women stood up beside each other and presented their chest, without removing their outfits I must say.

I moved along from Leyna, "to small for me," but she was my sister and they all laughed.

Tony had the largest and I found them excessive. Jamey was of course wearing her falsies but they were quite nicely shaped.

"Jamey, I think yours look nearly perfect on you," but the other four scolded me.

I looked at Celone carefully for the first time and then stepped to Florence. The two sisters were both beautiful but Celone wearing her heels was an inch shorter than Florence yet her breasts seemed perfect to my eyes for her height and figure.

"Celone has to be have the best pair here today," I said.

"See, to some guys big isn't best Tony," Tony smacked my hand away as I reached for her.

Celone hugged me as the others moaned. She whispered, "Maybe I'll show you them up close Keith."

The conversation turned to the planned trip with Jamey to Singapore, "We travel in three weeks. That will allow Jamey at least two weeks of rest."

Celone came over as the girls continued to discuss the surgery, "They will be married while visiting our mother," she told me.

I told her it seemed a bit fast, "Florence feels that Jamey is the one. I agree with your assessment Keith. I'll be moving out next week before the trip. Nowhere to stay, lonely too."

She was seducing me now!

"You could come stay with me for the week before the trip. Nothing permanent you know. The spare room is available when Leyna heads north on Monday.

"Tuesday," Leyna called out. My sister had heard us talking. I saw her cheeky smile.

It was settled, I would have a roommate for at least six weeks until Celone's new condo was ready.

When Celone arrived I had already placed her temporary wardrobe boxes in her room. She shared the news of the hospital visit.

"Jamey is in heaven. Her bruising is subsiding and it should be imperceptible by the flight to Singapore in ten days.

She explained the trachea and nose work, "Jamey will never be mistaken for a boy, that's for certain. Flo is over the moon happy."