Watching Jenna

Her fingers were at my chin and slowly she brought my head up.

"Then I will go slow. I wanted you to come home with me but we can wait. I can show you my collection. You remind me of someone and you'll enjoy the similarities."

As she stood she said, "Really, virgin? Wow and whoa!"

"I have to pee and settle a ride for Monica," she started to walk away, to cross the crowded floor but stopped and looking back at me said, "I can't think of sleeping with Monica with you on my mind."

A moment later Tony returned with Keith in hand.

"Look who I have found!"

While Cathy was away with Monica I talked with Keith.

"You seem to be following me, "

"No way, I just found this joint because of one my homies. I went to school with these dudes. They said this was a raw place, girls and guys. I just came along for the drinks. One dude just scored a rap hit and has a pocket of bread. Free alcohol got me in the door."

We talked until Tony returned from the ladies.

"It's after midnight. I'm getting tried Michaela so can you excuse us Keith?"

He offered to get us some food.

Tony seemed off somehow so we politely said no.

"Keith and I will see each other next Thursday."

Tony smiled and rolled her eyes.

On the ride home I asked her what was wrong.

"Cathy wanted me to take Monica home. I couldn't do that. We came together and she told me of her failed pass at you. It would have been wrong to help her tonight. She got upset a little. Then I hear you've got a date with a big guy. Though I'm into girls I'm a bit jealous."

I told her thank you.

"Are you sorry you helped me with my hair and make-up?"

"No issues. You need to be allowed to say no."

We talked of Keith and the date the coming week. I told her that I hadn't been with a man before.

"Really girl, really?"

Then she asked if I was good to drive to my place. I hadn't drunk too much so we hugged in her parking lot at her apartment before I got into my car.

"Just remember that you're in charge, I mean, if you decide to sleep with Keith."

I told her I enjoyed the club.

"Just not the girls?"

We laughed, "I did enjoy them. Cathy is hot and she can kiss!"

Scene Three

On Sunday morning I received a text from my old teacher Cheryl :

' I'll be near Akron this afternoon. Can I stop and see you? '

It was a rainy Sunday just past eleven when I gave her the address.

She arrived for lunch with a bottle of chilled sauvignon blanc. I could see her lust as I opened the door. I had spent the thirty minutes preparing including applying some makeup.

"Whoa, Michaela you look gorgeous!"

Her first kiss was just appropriate, no tongue. I was glad to see her and we enjoyed the lunch. She was dressed in a taut pant with cuffs above her ankles exposing her heels. Her top was white and I could make out the details of her brassiere.

After filling her in on my new job and friends we moved to the sofa. The soft kissing turned quickly to passion. Her petting was making me very aroused. She knew of my boy bits and still wanted me.

"Cheryl are you real sure you can handle my transgender status? I don't want you to stop. Somehow my panty is holding me."

She pushed me back to the cushions as she slowly pulled my legs wide.

I watched as she removed her sexy top and released the bra clasp. She wet her fingers and touched her nipples.

"I'm aroused Michaela by what you're hiding. Pull your panty off for me please."

I moved my hips and slid the garment down without exposing my penis. She reached and removed the damp thong off of my legs and kissed the panel of the garment.

"You have a lovely scent Michaela. Now please show me what you want me to kiss."

I kept looking at her as my right hand pulled my skirt hem up. My penis had been somewhat affected by my hormones but I was still stiff.

Cheryl jumped close and touched my penis as our mouths found one another. Her fingers grasped my penis as her tongue played in my mouth. Then she paused and looked at my body and then me.

"I have never sucked a penis but I have played with a few big clitoris."

I watched as she dropped to kiss my body and then she looked to my face with my penis near her mouth. She slowly took me inside the warmth of her mouth and then moved off and licked my shaft. I hadn't had a climax with another person since I could remember and within a few seconds I came.

"Oh my god Cheryl!"

She didn't pull away and her mouth moved back atop my penis. I released into her mouth. She held me there as my orgasm subsided. As she moved to kiss me I could smell the semen. I reached to her pants and I touched her mons as I tried to apologize for releasing in her mouth but she pulled me into a kiss. I had never tasted semen before but the goo and her tongue helped me forget the issue.

She smiled, "Yeah babe that's next."

I rubbed the light hair on her exposed vulva softly as we kissed. We had not been to bed last fall but we had petted and kissed during the two dates we had. She typically would initiate the sex play just as she had tonight.

Cheryl stood and extended her hand, "to your bed Michaela."

We showered together and she spoke of the size of my penis while we rinsed under the water.

"Have the hormones affected your penis Michaela?"

She was nipping on my left nipple and her fingers moved across my butt hole. She lingered there.

I was focused on her touch and failed to respond, "Oh yes Cheryl my body likes having you there."

I was slightly stiff as she bent to lick my bottom cleft.

"You are quite oral Cheryl," I moaned as she played at the skin of the rim of my opening.

"Well you seemed to get big as you are stimulated," her finger entered my bottom slightly.

She told me that her first lover was into anilingus.

"Ever since I have loved licking the bottom of my lovers."

"Oh," I moaned as I pulled her up to kiss me. "My turn to lick some pussy please."

She shut the water valve. She kissed me as we dried each other. Having a woman hold my breasts was exciting.

"These are nice tits Michaela. Now let's get into your bed."

When I had lit the two candles I saw her digging in her bag.

"What are you looking for?"

She turned and hid something from my view.

"Maybe later you will find out Michaela."

I was lying on my tummy and rolled as I pulled her to me. I held her butt cheeks as I lower my head to her mons and licked her that first time. Her scent was clean but musky. My right-fingers felt the inside of her thigh. She was wet for me. I moved to my back and she straddled my face as I kiss her slit and my digit pushed on the lower edge of her vagina.

"Will you enter me Michaela or will we play as lesbians?"

I moaned and licked her as I pushed the finger inside her warmth.

"No boi-toy tonight honey," I whispered

I tasted her pussy juice as I licked my finger, "I like this stuff too."

She moaned and began to move about as I licked the outer folds and then slipped my tongue into her.

"You have had pussy before that is clear," she moaned softly as she reached and grasped my penis.

I mumbled, "no touch," but she said,

"For balance only Michaela."

She touched my breast with her other fingers as I reached up to fondled her nipples. I licked at her hood and kept focused on her button.

"Oh yes you can be at my pussy anytime girl," she squeezed my penis but then let go.

The moaning grew louder as she began to move about and buck a bit.

"Fuck yes, eat my pretty pussy please."

I was having trouble breathing but just as I pushed her upward a bit she screamed and my face was covered.

"Oh damn I love it, Oh fuck, oh, ah,"

She moaned again then put her fingers between my mouth and her clit.

"Enough my little pussy cat. I can't take any more."

She stayed until the following morning but had a long trip back. We had enjoyed the evening and made plans for me to see her when I traveled home in February.

At work on Wednesday morning Tony suggested that we head to the club again on Friday. I wasn't sure I wanted the attention that Cathy would press on me if she showed up.

"Yes and she will be there and she did ask about you yesterday," Tony seemed to be okay sharing the past she had with Cathy.

"The girl is pretty well-off and she is smart too. She may change you Michaela but the sex would be fun. It was for me. We dated over a year ago after her mother had passed. As a only child she received a healthy sized inheritance."

I knew Tony came from a broken family and my father had skipped town when I was five leaving my mom to raise me.

"I don't begrudge her the financial freedom but I simply can't keep up with her spending. I work for every dollar you know?"

I agreed but what did this have to do with Cathy's aggressive style?

"Everything Michaela. She wants more, more fun, more girls, more sex. She tends to get it too. I would say that since I met her she has had ten girls, maybe a few more. And three were my girlfriends before Cathy met them. That doesn't hurt, you know, all three weren't right for me anyway."

I looked at her as we completed the worksheet.

"The store had a good week huh?" I said.

After lunch she again asked about Keith, "Don't you and he have a date soon?"

I smiled but explained that he was called away for business and had called me Monday evening to reschedule.

"That's too bad, then you will want to go out Friday?"

Scene Four

The plan was that I would follow her home again but my car won't start.

"We'll just leave it here until tomorrow." I moved my things into Tony's car.

She saw the clear dress bag, "Whoa, that will cause a stir!"

I had found a small boutique and the sexy midi-dress with a plunging deep-V to highlight my small chest. It was backless and this would be the first time I would go out without wearing a brassiere.

"Thank god it's a mild night. That dress is barely there Michaela. You will drive her crazy."

"Who?" I asked but I knew it was Cathy.

She did another superb job on my hair in a partially up style and my face was dramatic with a smoky tone on my eyes.

"For the pièce de résistance! A Chanel lipstain, Temeraire, a real finish to make her want to kiss you, and maybe your deeper hidden lips too?"

I saw the affect. I felt like a goddess. Tony's work made me so beautiful. I touched her arm as she stood behind me together looking in the full mirror.

Her dress was great as well but she said, "I just don't have your facial structure. This was easy because you are just more striking Michaela."

She hugged me and we stepped out to her car.

At the club door she again suggested the choker.

"It works Michaela. If you would rather not it may be crazy. I mean, you look like you want to be fucked, you know? I wanted to stay home and play with you."

Tony clicked the catch into place.

Seeing the mirrored ball spinning as we walked to the tables beyond the dance floor made me realize that I had caused a stir. It wasn't as predominantly women in the club tonight. More of a mix group. I didn't see Cathy as of yet. That's when I realized how the week had changed for me. Cheryl and I had made love and tonight I wanted her, I wanted to be with Cathy.

Last Friday she was too much but tonight I had dressed for her.

After my second white wine she strode across the floor looking glamorous. She was paused by two girls dancing but she had seen me and as she spoke to the two girls her eyes never left mine. I knew tonight was going to be difficult since I still hadn't come up with a reasonable explanation for my concealing my gender change.

After coming to our table she spoke only to Tony but kept glancing at my legs. I had worn a seamed nude toned pantyhose and the dress slit exposed a good deal of my thigh. She didn't even say hello for the first thirty minutes as her and Tony talked quietly.

Finally she moved to me and asked, "Hello Michaela, you look like you want to dance." She took my hand loosely.

"See you Tony. I want your girlfriend to play with me. Do you think she is too shy for that?"

As she held me during a slow number she whispered into my ear, "You look wonderful."

She was rubbing her upper thigh against my pubis. And somehow my trapped penis stayed concealed. Aa she kissed me after the third dance I knew I would be with her.

During the lingering kiss I had nearly climaxed into my thong as Cathy purposely played and aroused me. I was panting with excitement.

During a fast song her twirl exposed her black garter holding her stockings. As she spun and danced I thought I could see her pussy. She wasn't wearing a panty? At one point she pushed her dress aside and touched herself. I watched as she licked her own juice while her other hand held mine. She smiled at me and kissed me.

"Taste me Michaela," she kissed me with her body tightly against mine. I tasted her pussy on her tongue.

"I need to be released. Let's get out of here Michaela."

Her kiss was so intense as her tongue entered me. I touched her lower back as her large breasts pressed against mine. My little penis was moist but still restrained by the thong panel.

When we had stopped dancing she pushed me further into the booth while abruptly sitting.

"I have Tony's permission to take you home. At least I'll drive you, I heard of your car problem. We'll see what happens once we're at my place?"

I looked over at Tony. She was giggling.

"I knew that dress would send Cathy over the edge. Good luck Michaela."

Cathy kissed me and touched the choker.

"I want you to come home with me. I'll show you my home and we'll see if we can be good for one another."

Cathy headed to the powder room asking, "Do you need a visit Tony?"

Tony waved her off.

Next thing Tony sat down next to me, "She can actually be quite amazing."

I can't explain how Cathy had seduced me. I sat considering an adventure with her while listening to Tony say something about AAA. I didn't have any commitments for tomorrow and the car could wait. Would I let Cathy have my body? Should I explain my sexual history? Though I could get hard still my penis was quite small due to the hormones. I wondered if I could actually penetrate Cathy. How would she respond when I told her of my penis? I didn't want her to be upset and was uncertain what to do.

Tony didn't know I had a penis. I looked into her eyes as I considered telling her. Then I realized that it might destroy our working relationship.

I said instead, "How much older is Cathy?"

"She is twenty-seven. She was with an older woman for nearly two years. I think the woman was a doctor. It was a mutual DS relationship. They shared the role though. She loves sex Michaela. She may try to fuck you with her toys tonight. You are in charge. You could go home with me."

I considered what might happen later at Cathy's and whether I could find a way home if the penis beneath my dress became an issue.

I asked, "When was she last with a man?"

Tony looked at me considering the question, "Within the past three or four months. She loves a cock in her bottom. I can't figure her out. She loves pussy but needs a fuck too."

Over the music I couldn't hear well though she was at my side, "Cathy's life is comfortable. Nice apartment, a good job as a legal assistant. But she works hard. She is also, as you can see, a bit of an aggressive lesbian. And she can be quite lewd Michaela."

I smiled subtly, "Will I be okay with her Tony?"

She hugged me, "If you're frightened come back with me sweetie."

I looked into her eyes briefly but was now certain.

"I'm sure I'll be fine with Cathy tonight."

I considered how this night had unraveled, "Why did you give me the choker again?"

She just smiled.

Cathy's car was a cool little 'bimmer' as she called it. I had never ridden in a BMW. She talked softly now that we were away from the noisy club.

"I do drive a bit too fast," she seemed comfortable and I sat looking at her.

"You've never had a cock inside you?"

I turned and shock my head no.

"I'm amazed. A girl with that cute bottom and smile and you somehow stay fresh?"

I was quiet most of the ride to her condo except to say, "I'm new to the region Cathy and Tony's has been a great friend."

I also talked of home and she understood that some boys had abused me in high school.

Cathy reached for my hand.

"I'll take care of you," she then moved her hand to my thigh covered in the pantyhose. We were stopped at a light.

"I want you to feel my pussy," she surprised me again but I reached as she pulled her dress upward.

"Wow, you're so wet!" I whispered.

She moved and kissed me as her legs clamped onto my hand.

"I wanted you last week. I asked Tony to try and get you back to the club tonight."

The kissing continued as the light turned and someone behind us honked.

She continued the kiss without moving as the horn blared. She held my right breast but also opened her legs slightly.

"Taste me Michaela."

She began to drive but looking across to me I brought my wet fingers to my tongue. I felt so sensual with Cathy and her pussy was the first I'd ever tasted; twice tonight.

I must have moaned as I enjoyed her essence for she said, "I love that you are mine tonight. I'll get you to orgasm several times honey!"

As we walked up the steps to her place she said, "I want you to change when we're inside. I have your outfit ready. Please use the toilet. The white lingerie I set out was because I'll be your first."

As we entered the generous open space she hit a button and the dim lights and the screen in the living room came on. It was quite large TV and in a blink a movie started. It showed a girl with light brunette locks. She was small but wearing very tall white heels. Her face looked a lot like mine. The action stopped and Cathy took my hand and walked me to the screen.

"This is Jenna. I like to watch Jenna. She likes both girls and men. She loves her pussy sucked and her ass fucked. She is amazing. She is short like you too."

She hugged me from behind as I stood looking at the woman and her lingerie. Cathy turned my face and we kissed. Her tongue was in my mouth and her hand was on my dress-covered ass.

"Have you been with a girl, I mean, have you at least lick some pussy?"

I took this as an invite and dropped to my knees while I lifted her dress. The small thong barely covered her pussy and I moved it down as she held my head.

"This wasn't on the agenda but I like your willingness to explore Michaela."

I first looked at her body and then extended my finger to the top of her shaved mons. My tongue followed as the finger slipped along with her wetness. I restrained myself by only lightly kiss her hood. Cheryl had helped me understand this sensitive little concealed penis.

"Oh my, you actually can eat pussy!"

She stopped our foreplay and stepping to the Kitchen said, "Please,"

She pulled her thong up and continued, "Now go into the bedroom. I've laid out your outfit earlier for you. Jenna will wait for you."

She kissed me, "My pussy tastes good, hum?"

I nodded as I turned toward her bedroom.

"Don't, I mean please don't question the shoes."

I wondered when I should mention my penis but I was new to this and simply walked to her bedroom suite. I heard my silver heels clicked on the polished concrete floor. Seeing the bed covered with the white garments I thought of her confidence that I was coming home with her.

I put my hair up in a cap Cathy had left. The shower was large and had three heads. I thought of her pussy. I could smell her on my upper lip still. I considered that she was anticipating fucking my pussy tonight and what might happen when she sees I didn't have that special spot.