Watching Jenna Ch. 03

"Aren't you worried about getting sick?"

I chuckled, "Not really though safe sex is essential. Are you suggesting that fear has contributed to your staying clear of men?"

"No, well maybe, not exactly Keith but I do not have sufficient experience to select someone to sleep with that is healthy."

I told her than she would need to relax a little.

"You can't go into a relationship with another woman or man without some openness Leyna. You should relax and let, I mean to say, suspend judgment until you need to. They're doing the same thing; worrying about you too."

"I guess I hadn't thought of it that way before but it makes sense Keith. See why I needed a big brother."

I received a text from Cathy as we sat waiting for the check:

' so is your sister coming to town '

I smiled and turned my phone and snapped a picture of Leyna.

"That is sure to cause some trouble," I said.

Cathy was quick with a response:

' wow! tell Leyna we're all looking forward to tomorrow night '

Leyna pouted slightly, "I wish you had not sent her the picture Keith."

She said meeting new people was not easy due to her looks.

"I know the pressure is from me personally and doesn't rise from them, your friends, but yet I'm still anxious."

I suggested that we head home. It was after nine and she was still tried from the trip.

Scene Thirteen

Leyna lay in bed after a shower thinking of what her brother had suggested; 'You need to relax'.

She occasionally touched herself and tonight she needed some relief. She close her eyes and thought of the woman at the station yesterday afternoon. Her smile and scent had been a pleasant surprise. The woman had sat across from Leyna and when she moved her knees Leyna had glanced and saw that the woman was bare and purposely exposing her body for Leyna to see.

Though there were others about Leyna had watched this older beauty reach to touch her pussy with her finger. The sexuality she exhibited was alarming yet Leyna now recalled her own excitement as she rubbed her small penis quickly. The stranger had one hand at her pussy as her other touched her breasts through her blouse. Leyna saw the stiff nipple tent the woman's blouse as she caressed herself.

"Ohh, god, yes," Leyna moaned as her orgasm was quickly reached. The small release Leyna wiped from her fingers. Then she fell asleep easily.

In the morning her thoughts of sex didn't disappear. Keith's friends would not know of her past and she was absolutely not going to volunteer the information. Sandra had been most clear.

' treat this information like a girl treats her virginity, sacred and for just one person, the right person '

She knew that Keith was right though. She had to move passed the fear that had begun so long ago while she lived a restricted life with Sandra. It had never left her, the fear of discovery and Leyna had fabricated a tall wall about herself. It had taken her mom months to get her to reach out to Keith. Now she saw her hesitance as silly.

I heard the coffee mill working and knew Leyna had got up early. She was sitting with a coffee when I came out of my room.

"I heard you get up over an hour ago. Is everything okay?"

She told me she was good and had been thinking about what I had said regarding suspending concerns.

I paused her though, "But after seeing the affect you had at the Gallery I may be jumping to use my standards. Your behavior is tempered by the scene you can cause Leyna, and if a strong willed guy was to be attracted to you I do now understand your reserve."

"But I almost hide, you know. I mean I wouldn't be going to a strange club without you. Even with another girlfriend Keith because I worry."

She was controlled by her fear of being exposed. Her concealing her gender was the trap. Few men would believe her actual sex if she found a need to explain her history. She did not just pass. Leyna looked female.

"Maybe then you should consider reassignment,"

"No way," she interrupted me, "the risks are great as are the complications too. You just don't see the failures. The high profile reassignments such as Geena and Andreja make it appear safe but I have heard of very bad results too."

I was not certain who Geena or Andreja were but I didn't ask either. I wanted to help her, "Then you need to make more friends and build from that, not hiding in fear Leyna."

She stood and looked to the window, "Maybe I need some lessons on being with men, and women. There is no easy way to learn with the fear of failing Keith."

I could see her body profile as she stood with the sunlight beyond. The dressing gown did little to conceal her lovely shape. I wondered if she was asking me to seduce her.

"Do you really want me too Leyna?"

She didn't turn but I noticed her head drop. It was too quiet.

"Maybe it could help Keith. Just to be held and not be sexual."

I considered that in the three months we had only loosely hugged except that early morning when I had needed to pee.

"Leyna, I'm a man and though you are my sister I wouldn't want anything to makes you leave my life now that you are here."

I wondered if a sex therapist might help.

"I have spoken to one Keith. She points to my hiding years ago with Sandra as the psychological trauma that has caused me to be troubled with intimacy. She told me to suggest it to you."

"Well that seems nuts sister," I barked.

I stood and went to the Kitchen using the counter as protection from Leyna's suggestion.

"She, the doctor, suggested that we could just keep to foreplay and not actual, you know."

Now she had turned to look at me.

"I need some guidance Keith and you,"

She was now crying softly and brought her hands to cover her face.

"I'm so ashamed that I have made you uncomfortable, but you could be my surrogate."

I saw her stand tall as she spoke these last words. She meant them. She wanted me to practice with her. She wanted me to be her guide, an alternative to an actual lover. It seemed crazy except now it didn't.

"Tell me about the therapist and all."

She had seen Doctor Claire three weeks ago. After her last visit and the morning of my stiffy. They had met three times and the doctor felt I was the best adjunct with some respect for her needs and I was healthy.

"But what if I'm not?" I wanted to escape the role she was painting for me.

She took two steps and I saw her slipper cover feet for the first time.

"I can understand your trepidation Keith."

"Doctor Claire suggested we wear these."

She placed on the counter an envelope. I could see that there were two masks of some kind.

"You're kidding Leyna? A lace mask is suppose to help me lay down in bed with my sister?"

She moved a step closer, "Yes Keith. I'll meet you in my room in five minutes. I need you to do this for me."

I watched her leave quietly considering her proposal. It was insane to me to consider her request but she had what amounted to a doctor's permission slip.

"I am not following you Leyna."

"Yes you will Keith, because I have asked you to. You will."

Her confidence had me. Just like yesterday in the Gallery. She seemed to be willing to work through her difficulties. I sat down on the sofa. A few minutes later she called me.

"Come on. This is awkward for me to."

I stood near to the guest room door but did not enter. I was looking the opposite way to avoid seeing her.

"Do you understand what this is?" I asked.

I heard her shift on the bed, "Of course and the doctor suggested some ground rules."

"Oh?"

"Yes, initially she wants us to simply be on the bed, together and clothed. She recommended light touching but no sexual contact."

"Humm,"

Leyna told me the doctor's want her to become comfortable with relaxation and sensual intimacy and touching. She also told me that the doctor felt this was a better step than using a one-on-one consultant or sexual surrogate. Her needs were real but Leyna was fragile and yet she wanted to get passed her fears and enjoy some level of sexual intimacy. It was more about having some level of sexual satisfaction.

"So we're agreeing to only touching and no sex?"

"Keith please come here and just try to not be judgmental."

So we hung out on the bed. She wore the long gown and a mask of black satin. Mine was red. We hugged and I did get a little hard. She just looked at the bulge in my pants.

"Maybe for the next step you could be naked Keith?"

She had never seen a normal penis. After an hour I relented and removed my shirt and socks but not the pants. She changed her gown for a black satin slip. Now when I was lying beside her and saw her beautiful body I stayed hard.

"Now try and keep focused Keith. I want you to remove your pants, but not your boxers."

"How do you know I'm wearing any?"

I was eventually naked lying against my sister and my dick was soft.

"Now Keith the doctor hoped that I would be comfortable removing my chemise. I'm ready."

We had been on the bed for about ninety minutes.

"Okay but I'll look away and I'll slip beneath the covers."

"That's a good thought Keith."

Knowing she was naked now caused my penis to stiffen. She was on her hip looking at me as I lay still looking at the ceiling.

She touched my body first, my chest but this didn't give her pause. Now her fingers moved down slowly to edge of the sheet covering my crotch. I had been shaving my chest for years.

"You are smooth," her fingers stayed just above the end of my cock. My eyes were shut tight.

They she took her finger and ran her long nail down the length of my penis. I was covered by the sheet but it was still my sister's finger and it was my penis.

"Take care Leyna. That nail is sharp and this is quite close to sex."

"Okay and yes. This has been amazing."

She moved quickly but I saw her get out of the bed and hurry to the Bath. Her naked breasts swayed and I saw her butt cleft.

"Keith, that was successful. Let's get some lunch?"

So that event was behind us. At least I thought so. I enjoyed the guacamole salad she had made. She was wearing her gown again but she stepped to the other room. She called her doctor and described the morning. I could just hear her side of the conversation.

"Yes he did get hard. Yes I did touch it but only beneath, I mean the sheets covered him."

She hung up and walked back to me.

"Doctor Claire wants me to, she wants me to watch you masturbate."

"What? What kind of doctor, "

"She doesn't want me to be involved but she feels watching you is important Keith."

I didn't like this now, "She understands that you are with your brother right?"

I relented after she reminded me that I had agreed to try and be helpful. After she was under the covers I walked in with a towel about my waist.

"Can you sit on the coverlet?" she said.

"You know that I have never jerked off with anyone watching?"

She asked if I needed some porn?

I grabbed the remote and selected the channel. There were two women with a guy and it was still weird for me. After ten minutes another scene started. This was a woman dressed in sexy white lingerie and stockings as she danced for her partner in a sun filled room. She even had a black mask over her eyes.

I watched as the woman played with her breasts. I was not hard though. Leyna was there but she was covered by the sheets. I watched while the woman sucked on her hard partner and something began to stir. Seeing this woman's pussy spread by the fat cock while the flimsy panty was pushed to the side and her white stocking covered legs raised high did it and I became hard. The lighting changed in the guest room where we sat watching this porn thing. The sun must have slipped behind some clouds.

After a minute of watching the guy rubbing his cock over the tight hole of his lover caused me to moan. I saw the man line up over the girls' asshole and she took him deeply into her bottom.

"ahh ugh," I whispered.

I climaxed as the view shifted and he entered her ass. The anal penetration was too much.

Leyna shifted and I felt her touch my back, "I think that is Jenna."

She reached about and touched my penis.

"Can I feel your semen?"

I was bewildered by her statement and now her question but she now held my cum covered penis.

"That's a lot of semen right?"

I jumped up off the bed.

"Alright that is too much Leyna," but I saw the woman pumping the dick on the screen as the man shot all over the woman's face.

"What? Who is Jenna?" I said.

Leyna sat up as I turned and I saw her bare breasts for the first time.

"It's Jenna Haze and I was talking about the load she had on her face Keith."

"You know this woman?" I asked Leyna.

She giggled, "No, but yes. Jenna is famous for her love of anal."

I was beside myself and stepped out of the room holding the semen-dampened towel about my waist.

Scene Fourteen

Twenty minutes later she came out dressed in a beautiful black dress and heels. Her face and hair looked amazing. She quietly sat down at the counter.

"I was able to, well I did orgasm after you had left Keith. Thank you for sharing with me today."

She turned to take a drink of water.

"You may not comprehend how important a step this was. I just spoke with the doctor and she is happy. Thank you Keith," she moved around the counter and kissed me on the cheek.

"So then we're done, correct?"

Leyna then told me what the next step would entail. I reacted negatively to her suggestion. Her voice broke as she explained how and why it would be helpful for her.

"A surrogate would be a worse alternative Keith. Please think on it rather than closing the discussion with a no."

She returned to the guest room and I did not see her for thirty minutes.

She came into the living room where I was reading and I noticed she had changed.

"Why did you change out of the dress?"

She didn't answer as I looked at her bottom in the sexy leather pants and her high heels.

She asked, "The plan for dinner is?"

I looked at her.

"I'm still not ready to do what your doctor wants. You can parade around naked Leyna but I cannot see how my sister's learning fellatio with me is a good thing."

I fidgeted on the sofa as Leyna paced.

"Maybe we can go for a drink?" she asked.

I considered whether I could keep calm. Her outfit was quite distracting.

"How about using a fake penis, shit a banana!" and I stood to step to the bath and relief myself.

As I peed I wondered if this was possible. Could a woman actually propose such a thing? Incest was at the core of bad family behavior and I still was getting over that she was born my brother. When I walked back to the living I grabbed my coat.

"Yeah, let's walk down to the corner for a beer."

When I entered I knew I had made a mistake. Estonia was named by the recent owner but the crowd was the same since I had been coming here over the past year. A few guys waved or nodded hello but their eyes stayed focused on Leyna.

"Hey Keith are you going to introduce me to your girlfriend?"

I was Jake who ran a small ad firm near my office.

"Oh Jake, hi. This is my sister Leyna. She is staying the weekend with me."

Jake was an older dude that I hung with on occasion but Leyna sat down next to him on the empty stool.

"I'll just stand," I said. I watched him and was uncomfortable. He clearly was interested in my sister.

"My brother has been hiding me for months. He has protected me but I needed to get out. With him at my side I can and not fear any lewd come-ons."

Leyna smiled and I saw Jake move back a bit.

"Well," Jake said and smiled, "He has a beautiful sister and I would do the same. I mean protect, I wouldn't want, shit Keith is right to hide you Leyna."

We stayed for two rounds and Jake bought both of them. Leyna seemed to just need me there for I barely added anything to her and Jake's conversation. I learned more about her by listening. She was a magnet though and after some time I noticed that we had a clutch of other guys around us. They weren't difficult but clearly Leyna felt special tonight. Her smile seemed to do most of the work. Jake's flirting disappeared and he enjoyed her company.

As we parted the crowd to leave I saw the lust in the eyes of the men and wondered about her request anew. I realized that she had wanted me to see this display of their lascivious need. She hadn't acted inappropriately nor was she jerking their chains. It was just she caused a stir everywhere.

"I like this Bar Keith. Everyone is so friendly," she said as we walked out the door. I had forgotten about eating.

I stopped a moment as she walked ahead and saw several sets of eyes trailing her. My eyes were on her bottom moving in those tight leather pants. Her sexy heels seemed to click with the beat of the song playing. I could see something might happen.

"Are you coming Keith?" she said as she turned and caught me and the others lewdly reviewing her body.

At least no one whistled.

Once on the sidewalk she said, "So Keith, do you see why I need your help? I would never have walked into a place like that on my own."

She reached for my hand as we started to walk the block back to my place. Then I remembered that we hadn't eaten.

"Let's stop at the little pizza shop?" but I saw the look.

"Okay there is a Holefoods down two blocks. We can get something there."

She didn't let go of my hand until she saw the grocer. The talk was mostly about the women who modeled with her.

"We need to stay thin of course but many of them are bisexual."

"Then why not ask them to help with this sex stuff?"

"Because, then they'll think we are dating, a couple you know?"

I didn't see the downside but she then said, "It's a very cat like jealous that we have between us. If I get to do a good show then several girls won't talk to me for days. I try to not reverse the condition but being passed over hurts, a little."

We sat at the Holefoods café and ate our oddly varied food; my thick meat sandwich led to the discussion about my health. I liked having Leyna rib me. As I cleared the table I saw Michaela in the checkout line.

"Come on. There's a friend I want you to meet."

Michaela was surprised when I tapped her on the shoulder.

"Keith!"

After the hug and the introduction she asked, "So Leyna has been keeping you away from the Club?"

I explained that we were going home to get ready.

Michaela smiled, as she looked my sister up and down.

"You know I tried to date Keith," Michaela said slyly.

I interrupted her, "Well yes but since then Cathy has convinced you to stay with her. It would be awkward now Michaela."

"I'm just teasing your brother. He did say you would be in town but never did he tell me what a beauty you were."

Michaela pushed me away from her side kiddingly.

"But we'll all dance and enjoy tonight," she said. "You could wear that Leyna. I think I might switch my planned outfit if you do. Cathy loves the way my ass looks in leather."

Michaela explained her relationship with Cathy subtly without many details.

"Cathy found me and she seems to want me to stay,"

Leyna smiled as she shyly asked, "I would think having a lover would be grand?"

I saw Michaela wince slightly, "Grand but any relationship requires each person to work at it."

She was implying that Cathy was less than sincere.

"But you will meet her around nine-thirty and Tony and the others, Monica and Suzanne. Oh, and Keith do you know Celone?"

I told her no.

"Well I'll see you both there. Celone and her sister Florence have a good friend staying with them, Jamey. She was a singer until recently. Anyway, until later."

She cheek kissed my sister. It amazed me how quickly women could become friendly.

As we walked home Leyna said, "You know she wants to sleep with you Keith right?"