Watching Jenna Ch. 03

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The discussion continued the remainder of the way but I resisted her view of Michaela.

Back home we had some wine as she decided on her outfit.

"Is Michaela right? About the leather pants I mean? Could I be dressed like this?"

I turned and saw that she had on the pants but had changed her top. I could see the soft lace of her bra through the nearly sheer top. Her nipples were hard. She was excited and I had to squeeze my leg to prevent my boner from being apparent. She smiled.

"Yeah, I'll wear this then," and she walked to the bath.

"I will need a few minutes to adjust my face. That will allow you to square the issue in your pants."

Scene Fifteen

When we had passed the bouncer at the door and walked across the dance floor I saw Tony and Michaela alone at a tall table. They waved to me and Leyna released my hand and moved on her own to say hello to Michaela.

"I know at least two people in this crowd," Leyna said as she again kissed Michaela's cheek.

Michaela said, "Wait about an hour Leyna and moving in here will be almost impossible. This is my girlfriend Tony. We work together."

So as these three talked I looked around at the crowd. I saw an old friend but just waved. She was with a guy I did know but didn't like. No need in screwing them up I thought as I heard Michaela talking about Cathy.

"Tony, she is different. We spend quite a bit of time together,"

Interrupting Tony said, "Yeah with you tied up or something."

Leyna offered, "Cathy sounds interesting Michaela. She is more than a little dominate. Tie you up? Really?"

Tony just giggled, "Maybe with loose silk ropes Leyna but she is a little like a predator."

Michaela told Leyna of the history between Cathy and Tony.

Tony blushed, "I did find you attractive Michaela. I didn't want Cathy to keep you."

I came back from the bar. I brought a cool bottle of Chardonnay and four glasses.

"Nice Keith," Tony joked. "Cathy was sent to get us a drink twenty minutes ago. She may have a new girl trapped in the bathroom!"

That was too much for Michaela as she punched her friend lightly.

"Excuse me Tony but I may be in love with your ex so keep it civil please."

I had explained to my sister that many of my friends were gay on the ride over to the Club. Leyna seemed to be enjoying these two. We finished the bottle before Cathy came back but without the drinks.

Tony smirked, "Out on patrol Cathy?"

Again Michaela banged her arm.

"Ouch, twice no more, I'll lay off the smart-ass comments," Tony said as we saw Cathy kiss Michaela.

Pausing the kiss, "Oh hello Keith, who is this?" as Cathy noticed my sister.

With Cathy's arms about her waist Michaela introduced her lover.

"This cannot be your sister," Cathy said to me with a smirk. "The picture Keith, you are not a photographer!"

Leyna smiled as Cathy picked on me.

"You are okay looking for a man Keith but she is way to beautiful to come from the gene pool that spawned you," Cathy laughed as her jab hit.

"Well she is and can I say that we aren't friendly enough for you to be picking on my sibling Cathy."

I wasn't hurt and the five of us chuckled.

"Excuse me a moment girls," Cathy said. "I think I see Celone and, oh yes their new friend Jamey too."

Cathy stepped away. her heels clicking over the pause in the music.

Leyna giggled, "She is something Tony but I also see her love for you Michaela. She's seems cool."

I watched as Cathy hugged the three women on th edance floor and pointed toward our spot. The shorter girl smiled at me as she saw me staring.

I heard Michaela ask Leyna about her work as I continued to look toward the four women. Cathy was moving slightly to the dance rhythm. She then hugged the tall girl.

Leyna tried to turn the discussion away from herself as I again looked about the large darken room. The waitresses all seemed frazzled due to the crowd size. It was getting tight on the dance floor too.

"I'll get us some more drinks, wine or?" I asked. With the list I stepped to the bar which was nearest.

As the barkeep worked I could watch but not hear the three women speaking. I thought that Tony seemed quite attracted to Leyna. Her eyes didn't leave my sister. Michaela was dressed in brown leather capri pants and a sheer top too. I had to keep looking away each time I caught a glimpse of her small breasts for she wasn't wear a bra. This sexy girl was for someone else it seemed. Cathy may be good for her but I was jealous and wished that we could have dated.

As the order was ready a waitress appeared and offered to carry the drinks to the table. I walked a few steps ahead and saw Cathy bringing the other three women to the table.

"I guess we will need some more please," I said to the waitress.

Tony introduced the three women as I listened to Celone order a special cocktail.

I was buying the round, seven women and me. I stood beside Cathy who was now tight beside Michaela. Leyna was in the middle of the group and I smiled at her since the music was loud and I couldn't hear the conversation between her and Cathy.

"Mostly I model for minor catalogs and some smaller City shows. You know, not the big designers, more the ready-wear stuff," my sister told Cathy.

Leyna was keeping them all focused on fashion so I just watched, listened and sipped my Manhattan. I had missed the name of the Celone's sister's girlfriend. She occasionally smiled at me but she was quiet compared to the others. She was smaller too as she was standing without a stool. The table had room for the five so three of us were standing.

Celone asked Michaela about her background, "When did you move to town?"

I listened as she spoke of the first months in Akron and dropping out of college.

"I have applied to the College, Cathy has helped me and the interview at State went well. Part-time study is easier for me due to my work."

Cathy smiled as she suggested, "You could go full-time Michaela. I can handle you quitting the store."

I saw the anxious look cross Michaela's face but Cathy didn't.

Celone spoke about how Jamey had joined them recently, "She just arrived on Flo's doorstep and has moved in."

Florence was rubbing her girlfriend's bare back. I didn't see Jamey's bra straps. I realized that Leyna was the only girl wearing one. As I listened to Cathy speaking about Tony's suggestion about college Celone slipped next to me.

"This is special Keith, I haven't seen a guy with this many beauties ever. You are holding up well."

I thanked her and smiling said, "My sister needed to get out and meet some new people. This Club attracts such a varied crowd. I love being with you girls. Those guys, look there," I pointed across to a table of four guys, "They can't image how they can move in. The estrogen at this table is kind of like a barrier."

"Well Jam," Celone started to say something but changed quickly, "We're not all on the pill Keith but the feminine scent is strong. I think that can pause a macho man."

I felt her hand touch my thigh, "You seem to enjoy our company. Maybe you could visit us sometime?"

Celone's fingers traced up my leg to my semi-hard dick tightly pack in my pants.

I turned but didn't move her hand, "It might be an interesting visit if you keep warming me like that Celone."

She kept her hand on me, her eyes looking intently, "My sister and Jamey would enjoy you and I would love to watch."

I knew I was going to meet these women but I just kept smiling as she kissed my cheek and stepped away. She moved back to between Jamey and Cathy and I saw her whisper in Cathy's ear. Cathy glanced slyly up and smiled. Then she looked over to Leyna and said something to Celone that I couldn't hear.

I looked toward Jamey who seemed to be aware of Celone's comment. She winked at me.

Then Celone whispered into Jamey's ear, "Michaela and you are sharing correct? I saw a text she sent you this morning."

Jamey seemed a little upset as she spoke with Celone.

"I think her and Cathy will fail," Celone offered, "I plan to offer her a refuge if necessary from Cathy."

Cathy stood and signaled Michaela toward the dance floor. She took her lovers hand and led her to beneath the mirror ball as she slow danced to a Eurythmic's song. Tony asked Leyna to join her and I watched my sister moving provocatively in front of the crowd. She seemed to be seducing Tony as I saw her hand rubbing across the girls bottom. Then Tony paused and kissed Leyna. I moaned slightly and Celone heard it.

"Keith it might be a good match," Celone offered but I was thinking of the ride home now. How do I get Leyna home. I respected Tony and she was a smart good looking woman. She might be good for my sister. Then I saw it, the deep and emotive kiss between the two as they danced.

Cathy and Michaela came back near the table but they seemed unsettled and each took an empty seat. Jamey was between the two lovers.

"I can shift so you can sit here," Jamey offered. Clearly something was up with the two as I saw a spark of remorse on Michaela's face again.

I turned seeing Tony lead Leyna to a corner as they kissed again. Tony's hands explored my sister's leather covered bottom. I worried how Tony would respond to the news Leyna had.

As the set had ended Tony and Leyna returned. My sister smiling stepped to my side and whispered as Tony held her hand.

"She knows Keith. She is cool and I really like her," Leyna said as she kissed my cheek.

I saw Cathy reviewing the situation and wondered what was up with her and Michaela. Cathy's eyes followed Leyna as her and Tony sat together but Michaela was now beside Leyna. These two whispered in a conspiratorial manner and giggled as Tony ordered another round.

Cathy wasn't enjoy herself now and she stood which seemed to allow her to hear the conversation more clearly.

Leyna spoke, "Thank you all for inviting Keith to this party. I wouldn't be able to enjoy myself like this. My small group of girlfriends are a bit more competitive."

Cathy offered, "I think we can make a show like that too Leyna. We're being polite and trying to relax."

Michaela now stood and moved to hug her lover, "Cathy, I'm sorry it upset you. Let's enjoy this song."

As the two danced off I heard Tony's opinion, "Cathy is usually the most beautiful girl in the group if not the room. Leyna has that spot tonight and Cathy's a bit piqued by the situation. She will adjust and settle down I'm sure."

I was uninterested in dancing since these six were fun and the pairs seemed to be settling. Florence's didn't let Jamey out of her sight and with Michaela dancing Jamey relaxed. I was wondering about their relationship when she turned just so and I saw her neck in profile. The bump was unmistakable. Jamey was like Leyna I wondered? My sister's neck was smooth but I thought as I considered her poise. Was it possible that Jamey was a male? I could be wrong so I looked away.

Being unattached I now was studying the group with a renewed perspective. Celone had walked off somewhere and I needed to pee so I excused myself. With all groups the dynamic was important. I was here for Leyna tonight and my goal was for her to have fun with some friends.

As I slowly walked back to the table I decided that I should respect the life Jamey was living just as my sister's world needed those around her to allow her to safe and normal. Jamey might have been born male but now I thought 'so what'.

It was after midnight when the eight of us all were about the table again. Cathy begged forgiveness.

"I was so being a bitch. Leyna, you are beautiful and I apologize for being nasty earlier. Michaela and I need to get to bed, I mean to head home."

I watched Cathy to see if she was truly aware of her behavior tonight. She stepped over to hug me and then turned to Leyna, "Welcome Leyna. You are my friend right?"

Leyna kissed Cathy lightly on the lips, "Friends Cathy. Thanks for tonight."

The women all kissed and hugged as the two left.

Tony whispered to me, "Cathy is going to bang her hard tonight," I realized she was a bit drunk but didn't say anything.

Leyna was now speaking with Jamey. I wondered if she knew Jamey was also born a male but I simply watched the two as Florence listened as well.

Celone seemed distracted for she was alone and was watching the others much as I was. Tony had clearly drank too much. Celone asked if I could help get her home and I agreed.

So the night was an adventure that Leyna needed. She helped Tony as the five of us exited the building and found the cars. I drove Tony's car as Leyna had suggested. I assumed that Tony would help us find her apartment but she had fallen asleep. Leyna just drove to my place.

I helped Tony inside as Leyna grabbed their handbags

"She can sleep on the sofa right Keith?"

So after a few minutes of sorting out the sheets and pillow I went to bed. Leyna stayed up to unwind as Tony snored on the couch covered in a blanket.

"Tony what's going on?" whispered Leyna as her new friend slipped into bed beside her.

Tony kissed her softly, "I know I'm doing something I never would have considered yesterday. Sleeping with a woman such as you is new to me so let us just see what happens Leyna."

Tony eased the panty off of Leyna's hips, "I like your body," she said as she bent to kiss the small semi-hard penis she found.

Leyna moaned as her lover licked her body. Tony's fingers reached to play at her nipples and Leyna moaned.

"Yes sweet Tony my tits are quite sensitive."

The two rolled into a sixty-nine position and Tony cried softly as Leyna's tongue entered her pussy.

"Eat my pussy please, yes Leyna, there," as Leyna's tongue moved along and across her clitoris.

Leyna's long fingers moved into Tony's body as her tongue continued on the hood of Tony's clit.

"God, god, yes, Leyna, oh shit, ohh,"

The scream was muffled as Tony came and pushed her mouth tight to Leyna's sex.

Tony moved back to the bed head and licked Leyna's face clean, "My god Leyna. I'm glad I had that last drink."

They fell fast asleep together after their lovemaking.

I was awakened by the sound of moaning near five in the morning. I walked into the living room and saw the empty sofa. Then I saw the glow from the video system in the guest room. The door never closed properly and the gap allowed me to look in.

Leyna was snug against her lover and Tony softly snored. The DVD control was between them. I looked to the screen to see the beauty with the white lingerie fucking that big black cock again and I got stiff. They must have rolled onto the button or fell asleep with the DVD running. I pushed the button and left.

When I was back in my room I considered what had happen over the past hours. I remembered the name of the performer. Jenna had made me hard twice today. My sister now seemed to be beyond my assistance, at least I could hope. Things could be worst. I heard Tony's noisy snore for I had failed to shut the door tightly.

There were changes happening in my world and most important Leyna was happy and sleeping with a lover.

To be continued . . .

By MadQuill

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4 Comments
MadQuillMadQuillabout 7 years agoAuthor
More of this Tale

The last two chapters are steeping. Michaela and her friends will be ready soon

MQ

AnonymousAnonymousabout 7 years ago
More story

Wow, we need to how all of this ends up. More please!

MadQuillMadQuillabout 7 years agoAuthor
Watching Jenna move

The arc of this plot brings these women into each others lives. Their individual evolution is clear but the complex relationships will develop in Watching Jenna IV

Thank you for reading,

MQ

AnonymousAnonymousabout 7 years ago
yeah another chapter

thanks again , another wonderful read cannot wait for more.please keep this going , reading the characters stories and growth is great.i have discovered i am transgendered as well. lots of love to you.

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