Watching Jenna Ch. 04

Please remember this is a copyrighted work and all legal disclaimers apply.

I appreciate that the poor grammar may take away from the tale.

Thank you for your comments.

The plot of this story includes the relationships of seven women and is tied to "Watching Jenna". "Watching Jenna V" is underway.

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Scene Sixteen

It was an awkward Saturday morning with Tony sleeping to nearly Noon. After I told her about the drive home the night before Tony saw that her car was outside. She quickly departed leaving Leyna and me to spend the afternoon watching old movies on Tmax and veg'ing out. I purposely stayed clear of discussing the night before until Leyna inadvertently hit the DVD player and 'Jenna' again appeared with the large cock buried in her bottom.

"Let's not watch her dance right now Leyna," I said as I grabbed the control.

"Yeah, I'll get you an IPA though. Dinner?"

We ordered Chinese and continued to watch several Hepburn and Tracy films.

Leyna left early Sunday afternoon for home. She texted me after she had gotten on the train.

' Tony was wonderful thanks for the introduction Keith '

I stopped the car and called her. Leyna giggled as she told me that Tony had met her at the train station and the two were traveling north together.

"Tony has decided to stay over Monday with me since she doesn't work tomorrow," so they would have some time together. The changes for Leyna were exciting and I hoped it meant her lessons could stop.

I clicked off the phone. Leyna didn't need me with her friend Tony showing her the ropes.

On the train the two were considering which car to sit in. The conductor had taken their tickets as they boarded the very long train. He said as he punched their paper stubs, "We're transshipping these cars back northward. The last ten cars are empty. Sit ahead of those."

Tony made for the rear of the long train.

"Tony he said we couldn't sit in those cars," Leyna whispered.

"But he didn't actually. He simply said 'sit ahead of those' and see this door is open. Come on Leyna. The back cars tends to roll about like a wave."

They made their way to the tail of the train and found the seats were looking out the back of the car. They sat for a few minutes enjoying the rolling action as the train sped up and the urban landscape zipped passed. They sat holding hands when Tony reached to touch Leyna's leg above the knee.

"You enjoy wearing pantyhose?"

Leyna felt the fingers delicate touch, "Yes Tony but many days the work requires them. I've grown accustom to the feel and don't tend to go naked except on really hot days."

Tony turned to kiss her sexy girlfriend. The seduction was easy as they were alone.

"See what I mean, the sensitive roll of the train. It's making me want you Leyna."

Their kiss began gently but Tony was ardent. She wanted this woman, here on the bench seat of the train heading north. Her tongue teased across Leyna's lips as her fingers continued to rise. With her other hand Tony reached behind and retracted the zipper of her lover's dress. There was no resistance as their tongues licked, sucked and probed each other's mouths.

"Oh yes Tony, I want this so bad, " Leyna moaned.

Leyna felt the clasp of her bra being released as Tony's fingers reached about to touch her sensitive nipple. The other hand was now atop the nylon fabric covering her pubis and Leyna shifted as the Tony's fingers pushed the waistband of the pantyhose downward. Tony's hand found the lacy top edge of the pink thong panty and though tight she pushed her fingers down to touch the little nub of Leyna's penis secreted between her legs. Leyna was moist.

"I want you in my mouth Leyna," Tony moaned as she paused her kiss and moved to pull the stockings and panty to her lover's lower legs.

"Kiss me some more please," Leyna asked, "I love how you play with my tongue," she breathed in the aroma of Tony's excitement.

Leyna continued, "like I am yours," their kiss continued as Leyna reached to caress Tony's breasts through her top.

Tony had moved her hand to cover the girls tucked little nub as Leyna sighed, "I wish I could make that scent, you smell so good Tony."

Tony was aroused and moved closer and covered her lover's mouth and her tongue pushed inside as the train moved along. Her fingers held Leyna's penis as their kiss continued.

"Now, I," Tony mumbled, "need to kiss your body Leyna," as she moved to her knees.

"Wow Tony you want me," Leyna signed as Tony bent down and licked her soft little cock.

Leyna closed her eyes as Tony's moist mouth caused her to stiffen slightly. The last time with Tony she hadn't climaxed but the patient woman sucking her now was determined. The little penis she had did become almost hard with Tony's attention but when Tony's long middle finger entered her bottom Leyna became erect, all two and a half inches.

"Now we're getting somewhere," Tony mumbled as she continued to lick Leyna with her fingertip slipped inside the warm bum to the first joint.

"Oh god Tony, never," but Leyna couldn't speak as the woman loved her body with her mouth and now pushed inside her bottom deeper.

A moment later Leyna moaned and Tony felt the small release fill her mouth.

"Your stuff tastes good Leyna," Tony said as she shifted up to kiss her lover.

The two held each other but Leyna's body was more exposed with her thong now near her heels. She reached but Tony stopped her.

"Please let me look at you. No one can see us," the rolling train was sweeping passed farm fields as Tony stood with her back against the train door smiling at her lover.

Leyna moved forward and began to remove her dress over her head as Tony smiled and her hand slipped into her jeans.

"You are so beautif," but just then the rear train door gave way and Tony slipped.

"Tony!" cried Leyna.

She jumped up and toward Tony. Tony's hip had released the latch and the door swung open and she fell down onto the deck. The roaring sound entered the train car as Leyna tried to reach her lover's feet.

"Oh my god, fuck," Leyna swore as she lunged and grabbed Tony's feet just as Tony hit the dirty metal outer platform. The wind whipped Tony's loosely clipped hair and then the clip blew off and away.

Leyna held both of Tony's ankles now as Tony bent up at the waist. The air rushed across the two women and Tony's hand reached to hold Leyna's.

"Now I can see you quite well Leyna," for Leyna was bent and her groin was completely exposed as her dress hem flew up to cover her face. Her panty was wrapped about her ankles.

Tony looked backward and saw the edge of the train deck just beyond her right elbow.

"Close, but I'm fine honey," she slid on her butt toward Leyna as the train continued to rumble on. Her pants were covered in dirt but she was otherwise okay and she pulled herself up and reached to close the door.

"No," she heard a voice and looked up the cabin to see a different conductor.

"You two shouldn't be in the back cars. Come away. I'll get that door closed, and locked."

Leyna reached and pulled her panty upward while she was still concealed by the tall seatbacks. The man walked nearer as she straighten her dress.

"You could have been badly hurt Miss. Dave was supposed to check those doors. He'll be reprimanded now."

The Conductor slammed the door shut and with a key locked it as Leyna moved head of Tony.

The conductor saw the dirt on Tony's bottom, "You would have hit the rails at over forty miles an hour young lady."

Tony smiled as she watched Leyna's bottom shimmy as the tap of the heels resounded in the empty train car.

My sister called me Tuesday morning.

"Keith it was wonderful to be with someone who shared her body so willingly. Tony was amazing."

I asked Leyna to keep the specifics light.

"But without your help it would have never happened. So you needed to hear at least that brother. We played for hours, "

"Leyna, okay but, to much information."

"Oh, then I won't tell you about the train either, but Doctor Claire is quite pleased. She still wants me to find a male to sleep with but she feels that sleeping with Tony was a major step forward."

Having my sister happy was good and she turned the conversation to her next trip south. Her doctor would let it rest though. I needed to resolve some other issues before Leyna's next visit.

Scene Seventeen

Cathy called me later the same day with her special request. She asked me to meet her for lunch near my office on Wednesday. I wondered what she needed to speak in person about. I did not share this with Leyna though.

I little past one on Wednesday we found a table and I ordered some coffee while Cathy asked for some white wine. She looked about.

"Is everything okay Cathy?"

She moved closer and told me that she was worried about losing her lover, "Michaela is great Keith," but she was unsettled with their relationship.

"How can I be of any help?" I asked a bit dumbfounded.

She whispered, "I don't want to lose Michaela and thought, "

I looked at her carefully. She was anxious as she spoke quietly again.

"You don't know Keith, that Michaela is a transwoman like your sister."

I was floored but somehow didn't react in a negative way. I sat listening as Cathy spoke but I was in my own thoughts as I considered this news. I had thought of Michaela for weeks as I masturbated.

"I feel that if," Cathy put her hand over her mouth a brief moment then continued, "my girlfriend really likes you Keith, and, well, I thought that you could have a chance to,"

Now I was alert and knew what she was after and I interrupted, "Cathy what are you suggesting?"

She wanted me to sleep with Michaela, "She needs to have sex with a man Keith. You are a good candidate and "

"You are asking me to do what Cathy? Fuck your girlfriend?" I said as I pushed back away from the table and almost caused the waitress to spill her tray as she walked passed.

Cathy hesitated but then spoke quickly looking at my eyes, "Yes Keith. I needed to share the request with you. She is not a genetic woman and Michaela like Leyna needs to experience safely having sex with a guy."

She told me that Michaela had dropped a hint regarding her conversation with Leyna on Friday night.

I couldn't believe this statement but spoke slowly, "Cathy, I have had years to understand the world of my sister. I am officially surprised by your news of Michaela as I am about the request. Are saying that Michaela has asked you to prepare this rendezvous?"

"No Keith, well maybe a little, " Cathy was smirking.

I shook my head, "I cannot see a 'boy', no way, Michaela too?"

Now she smiled, "You're kidding Keith? Really? Even the name, the chokers she wears. Now I won't believe you."

I had certainly spent time looking at her girlfriend but since she had cancelled our date weeks ago I tried to keep my mind on other things. As Cathy talked I was distracted by these thoughts.

"So I feel she needs to experience, " Cathy stopped talking.

"Keith, are you listening?"

I apologized, "Its just a crazy idea Cathy. My sister and now Mich "

She paused me, "Keith, they are both women, okay? Don't go there. Leyna is, I mean I would never have thought she was a male, "

I spoke quickly now, "disregard that Cathy. What you want me to, I just cannot see how that will benefit your relationship."

She stared hard at me, "Who said anything about me? I want Michaela to be happy. Right now I think she isn't but it may not be just about having a man. She may need more than I can provide and I want her to feel complete."

I still had an interest in Michaela, well now there was a small resistance. Cathy's statement did seem possible as I reviewed my memory.

"So you read Leyna the other night?" I asked thinking that I knew the answer.

She glanced down to her lap, "No actually. Michaela let it slip on the ride home."

Now I wondered if Cathy had guessed what Leyna had sensed about Michaela the other night. I didn't feel her attraction but my sister was unequivocal.

Cathy started to tell me about the past weekend. How on Sunday afternoon Michaela had went to visit Florence and Celone for lunch. Cathy had an assignment to complete so she stayed behind. She told me more about her job and how sometimes her Sunday afternoons were partial workdays. She had needed to address a legal document.

Cathy told me how welcoming Florence had been.

"Michaela stepped in and saw Jamey as Florence stood at the door. Michaela had worn a simple blouse, a skirt with pantyhose and tan wedge heels but she saw that Jamey was dressed in a LBD, sexy heels and full seamed hose'.

Florence had kissed Michaela on the cheek at the door, "We're doing some dress up. Jamey just received this dress yesterday from the brown truck. She, well, I think she looks great."

Cathy continued her description of the afternoon in a near whisper so I had to pay close attention.

"Florence was wearing a simple print dress but she had spiked heels on and her face was full glam too. Michaela thought she had under dressed as the group moved into the house.

"but when Celone came into the Foyer. She was barefoot and her cotton top was white with ruffles and she had on a loose pair of girl shorts. Michaela said that she could see Celone's nipples for the top exposed her breasts as she walked over to greet Michaela.

Jamey told Michaela, "The girls keep buying new outfits for me," and it distracted Michaela for a moment.

"Then Celone kissed Michaela and they all walked out to the sun porch."

Cathy seemed very focused as she continued, "Michaela explained to them that she had needed to step away from me, she needs some space."

After that Jamey brought in the wine and was serving when Celone said, "Jamey has been eager to experience something we can't give her."

Cathy told me how it began, "Celone walked to the chair where Michaela was sitting. Celone slipped down to sit on the armrest of Michaela's chair as she continued to explain what she meant.

"Jamey was quite turned on by Keith the other night and she wants us to help get her a big guy to sleep with her. Maybe it will be Keith, maybe someone else," Celone suggested.

As Cathy told me the story she didn't include all of the details of what happen next but she did explain that Celone asked Michaela if she had been penetrated yet, "By a hot cock I mean?"

Michaela moved back into the chair and pushed at Celone's hip to get her to move away.

"Excuse me Celone but that's a bit too personal, "

Cathy told me that she knew how powerful Celone could be.

"Celone is used to controlling the group and she had slipped to her knees next to the chair as she slowly lifted Michaela's dress hem and exposed her lingerie.

I watched Cathy, her eyes looked moist as she spoke of the event, "Celone then looked up at Michaela's face and smiled as she said unequivocally, "Is it though dear? I have slept with Cathy and know a thing or two about her interests," as Celone slipped her hands upward and caressed Michaela's pantyhose covered thighs.

"Michaela was surprised by Celone's actions Keith. Jamey and Florence had also moved closer, on either side of the chair. Then she felt Celone quickly shift upward and she kissed Michaela on the mouth. The other two watched as the kissed became more passionate and Michaela surrendered her anxiety."

Cathy looked concern and glance away as she stopped for a moment.

"It was no longer subtle Keith, but not aggressive. Celone was french kissing my lover!"

Cathy wept softly as she told me, "Michaela said that she did not touch Celone nor try to stop her caress as Celone's hands explored her body but as they kissed Celone reached down to her inner thigh.

"Michaela felt that Florence was near for she whispered as Celone's kiss continued.

"My sister isn't trying to push you Michaela. She only wants you to enjoy our loving."

Cathy had tears in her eyes as she continued, "Celone held Michaela and a moment later she grasped Michaela's small penis."

"Celone told Michaela that she was smaller than Jamey, "but Jamey doesn't want to fuck you she wants to be with a man."

Cathy's voice trembled as she continued, "Michaela's head was spinning and her arousal grew strong as Celone played with her genitals. She later told me that she had anticipated that Florence and Celone might make a pass that afternoon but the reality of the seduction had overpowered her. She heard Florence's talking softly.

"My sister wants to fuck you though," Florence said.

Cathy meekly told me what Celone said, "she told Michaela that they had all felt that something wasn't good the other night with me and they wanted to make Michaela feel welcome; to offer a safe place to stay. To leave me, "

"This is Florence's house," Celone told Michaela.

I looked at Cathy as she spoke with her head down. She was hurt by this but she wasn't finished with her description of Sunday, "Michaela told me when she came home that the idea of being with a man was incontrovertible in her mind after the seduction by Celone."

"Celone told Michaela that, Jamey and Flo want to be helpful too. They feel that they may aid her adjustment."

Cathy explained to me, "As Celone moved to kiss her again Michaela tried to move away, she turned her head to stop Celone's kiss and she reached to pushed the fingers playing in her panty away but now Florence and Jamey had taken her arms and gently restrained her.

Cathy continued, "She tried, Michaela tried to get up. Maybe she wasn't attempting to leave but to distance herself, but she asked why they were holding her? Why was Celone seducing her?"

Cathy then spoke with a quiver, "She saw it then, Celone had a strap-on about her waist and she exposed it to Michaela.

"Celone," Cathy now cried loudly, "she told Michaela that she seemed beyond my sex games when she had watched her with me the other night."

Cathy was nervous as she told me the story that her lover didn't feel trap but she needed to move away and to get some space.

The sound of Cathy caused a look from the waitress, but she continued quietly, "Celone helped her stand as Flo pushed her panties down," Cathy said, "and then Celone turned Michaela as the others held her and they slipped her onto her tummy resting atop the chair's armrest. Then Celone moisten her toy and rubbed it slowly along Michaela's body."

I could now understand that the three women clearly were interested in fucking Michaela but Cathy's story was confusing. So I asked her directly, "Did they rape Michaela?"

Cathy stated strongly, "No Keith, she wanted it. Michaela admitted that she had asked for this, for Celone. In her mind she knew she needed more than I could offer. She told me at home how she had enjoyed having Celone fuck her and loved the attention of Florence and Jamey as well."

I saw that Cathy's mascara was smudged. She was weeping as she covered her face.

"She wanted to cause me some kind of hurt Keith. Later that night when she returned to the apartment we discussed the afternoon and then she asked me to reach out to you. She said that she would decide about us afterward."

I was now aware of the background but was still paused by the facts of Michaela's gender change and the lascivious behavior Cathy had described.

Cathy calmed a bit and spoke of her lover's hometown experiences as she felt I needed to understand as much as possible about Michaela including her teacher and the aggressive boys.

"When she met Leyna last Friday night something clicked," Cathy told me.

"Michaela knew she wasn't alone, not totally. There were other women like her. Your sister and her barely spoke but they clearly had shared a moment Keith."

I didn't need any more details of Celone's afternoon with Michaela and wanted to seem supportive of Cathy but I wondered if I could sleep with Michaela, I wasn't sure so I held my thoughts.