Watching Jenna

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I hope that the story isn’t affect by the grammar errors. I’m sure there are some errors and I do care.

Thank you for your comments.

Scene One

It had begun many years ago. This feeling that I was different. Being smaller than most of the other kids in school was just one issue. I played hard with my friends but the tussle and wrestling just supported the fear that I couldn’t keep up. I’d play with the neighborhood girls when my buddies were off to the little league field. That didn’t lead to these feelings. The spike in my curiosity was clear and afterward I was resolute. I used the CPU at the Library to research my gender alignment but I knew that I was a female in my head. A long time would pass before I could act on this decision and therefore I hid my true self from my family and friends. Getting along was trying but necessary as the daily issues piled up.

After I reached my last year in high school and passed my eighteen birthday my mom saw I was unsettled and that my personal relationships were failing. One afternoon she sat down and asked me what she could do. I looked at her and considered telling her of my anxieties.

She talked all around the issue, “Why haven’t you been to see Jon or Charlie lately?”

I gave her an excuse and she jumped to another idea in her head.

“You should ask Mary out. I can tell she likes you.”

I rode from the same school bus stop with this beautiful senior.

“She wouldn’t give me the time of day mom.”

After a half an hour I had resisted opening up to mom. Then she did it. She said something I had needed to hear. She suggested she would do anything to get me to trust her and confide my worries. I realized at that moment that I could no longer remain quiet. I just could not conceal the truth of my gender identity.

“Anything?” I asked.

Ten days later I received my first hormones and my odyssey began. The changes due to the hormones were slow but still amazing. The doctor had said that my body showed signs of ‘delayed puberty’ and she had an x-ray of my hand done and a testosterone test ordered. The x-ray was actually of my right wrist and showed that my development was behind for my age at least two years. Having her inspecting my nuts was difficult. I became aroused as she held them.

“For a person considering female hormone therapy this is like a god sent. Your body hasn’t developed normally. Your testicles are quite small for an eighteen year old.”

She did not add that my penis was small too.

On the way home Mom also suggested that I should let my hair grow and begin to dress more feminine.

“With some careful selections we can begin to change your dress style honey.”

The next day she came home in the afternoon with several bags.

“I was researching gender non-specific dressing,”

I stormed out screaming back to her, “Don’t mom!”

She dragged the bags to my room.

“The look you could achieve could be non-descript or neutral.”

Later that evening mom shared with me an anxiety she had many years earlier.

“I watched you when you were nine. I knew there was something different but I didn’t know what I should do.”

I turned to her, “Well better late then never mom.”

I hugged her and started to review what she had bought.

The freedom she supported did change me in many ways but it was not easy to contend with the people that I knew. When the comments and aggressive behavior began I didn’t have a follow-up but to just skip school. Eventually the school called and she asked me about it.

“I go to the Library and read instead of class mom. Math class is especially not easy.”

I hadn’t been to school for eight days.

“Well the school won’t allow you to do that honey.”

Going back was hard for now the bullies had more to pick on. It made it difficult for me to feel comfortable. Those seven months caused me a lot of tears and some bruises. I had only to look at the mirror to remove the anxiety that school caused. I watched as my hair reached my shoulders and my breasts came to slowly fill my bra. There was another affect of teh pills. My diet changed and my body slowly became more feminine. My waist was at twenty-five inches and my butt increased to thirty-seven inches. Up top, well I was still an A-cup at thirty-four inches.

After three months I had to visit the doctor to have a follow-up checkup. In the car ride over mom asked about the changes.

“Do you want to keep doing this?”

I looked out the window and told her, “Yes mom. I have to deal with the fact that I’m not a boy anymore.”

“What do you mean?”

I told her about my thoughts and how my penis was slightly smaller.

“And besides girls don’t have one anyway. I can deal with it.”

Each day that spring I would consider my alternatives but I didn’t feel ready or independent enough. Thankfully graduation came and that summer I began dressing full time. The benefit of the hormones I started months ago allowed me to pass. Mom had a lawyer she knew prepare the documents to change my name and gender. In July I received my license to drive with my name, Michaela Wright, 5′-5″ 115 lbs. eyes blue, and dark blonde hair.

In the fall I began studying History at the nearby college. I was a new girl to my classmates since most of the students from my high school were studying elsewhere. During the second week of classes I ran into one of the bullies.

“Look who we have here boys!”

He was a big guy from my old school math class and he had two friends with him. I just ignore him as he hurdled insults toward me.

“Faggie little girl!”

Others nearby heard the nasty things they said as they followed me across the courtyard but the students just went about their business. After following me through two of the science assembly buildings and across a street they left me.

I saw the monster once or twice a week and he never failed to embarrass me in front of the other students. I wondered if I could ever have a normal life as a girl. At least he saw me as a female. That was some progress.

I was still living with mom so I would drive to the college. The parking lot was quite large. One evening in early November I walked to the car unaware of any danger. One of the bully’s friends was waiting hidden by another vehicle.

He jumped up and frightened me. I actually pee my pants a little.

“So just because I know about you does mean I can’t like you a little right Mic?”

I had the key in the car door lock but the door was still shut.

“My name is Michaela and I don’t think it’s a good idea. I don’t need that kind of attention. Please just leave me alone.”

He stepped closer and put his hand on the closed door of my car.

“I won’t be like him Mic.”

This guy was a big and I was wearing a dress and slightly heeled shoes. He towered over me.

“Please, just leave me be,” I asked.

He slowly reached to grab my arm but I moved a step back and pulled my handbag tight to my chest.

“Those little tits real?” he asked.

I had left the key in the lock and now he opened the door.

“Let’s get in the back Mic. I want you to suck me off.”

The thought of him repulsed me and I moved backward away from my car further. He had the back door open.

“Come on, I won’t tell anybody that you’re a cock sucker. Come on Mic.”

Just then two other students came near and I called out.

“He’s trying to molest me!” I called out.

The unnamed man heard and saw the tall guy standing close to me and he turned toward my car.

My assailant spoke quickly but quietly, “Okay Mic. Quiet down I was just having some fun.”

I watched him skip away as the girl and her boyfriend came nearer.

“Are you okay Miss?”

The following Thursday I had a night class and though I was parked quite closed to the classroom he had prepared. When I opened the car door I failed to see him in the back seat. A moment later he had jumped to the passenger seat and gagged me.

“I just want to be with you Mic.”

His violence seemed quickly to pass yet I shook in terror. It was after nine and dark and though there were lights the area I had parked was between them. I hadn’t considered the need to park near the tall lights.

He was actually speaking softly and was non-aggressive but still I was scared. It was late and there were few cars remaining in the large lot.

I looked down as he pushed my dress up to my hips and pushed aside my panty. I wasn’t wear hose’. His hands held my arms.

“Your little dick seems to be having trouble but I’ll get you to cum Mic.”

I watched as he bent down and took my limp penis into his mouth. Though I tried to restrain my excitement I slowly become semi-hard.

“Yeah little girl. I like that you have this in your panties.”

His hands were now beneath my bra and I moaned through the gag as he played with my nipples. I realized that he had released my arms and my hands went to his head, holding his mouth on my penis. I pulled the gag out and tossed it down.

“No one has ever done this to me. Oh dear, ”

A moment later I shot a small load into his mouth.

I was panting from the release but I wanted nothing to do with him.

“I’ll call Campus Security if you don’t leave now.” I had found my phone in my bag.

He smiled as I began to dial 911 and I saw a bit of semen on his lips. He seemed content and moved to lean against the passenger door.

“Don’t you want to taste mine?”

I was disgusted thinking of what I had allowed him to do. I opened my door and stood. I looked around for some help.

“Listen get out and I won’t scream. You can hear there are others close.

“Ahh Mic, just look at this.”

He had his jeans open and his penis exposed.

“Get out before I scream.”

He smiled as he turned and saw the group coming closer.

“Mic, I got what I wanted. You’ll come around and ask for more I’m sure,” and he got out of the side door.

I jump in and started the car. I could only move forward and away so as the group was now behind me I slowly left. He waved and blew a kiss. I turned and drove home.

I saw him later the next week in my large lecture class as well as in the halls but he curiously remained distance. I realized he was protecting himself rather than pushing me. I did not want his attention. I was only attracted to the girls in my classes not the men. He didn’t want to be seen with me.

One afternoon later that semester I received a note from my biology lecturer Ms. Sumner.

‘ please see me after class Michaela ‘

I walked to the front of the room as the other students left and she smiled as I approached. I had a frown on my face because he was still in the room.

“That’s what I wanted to talk with you about. I’ve seen him staring at you and wanted to offer to have a counselor speak with him.”

I said it was under control but she asked me to come with her to her office.

Once the door was closed Ms. Sumner moved quite quickly to my side as I placed my bag on the desk. I turned and she reached toward me. Her hand ran slowly over my bottom as the left one reached to my chin and she kissed me. Her warm tongue opened my mouth and she played with me.

“I’ve been hoping to kiss you since September Michaela.”

Her hand was caressing my bottom through my skirt.

I returned her kiss and her soft tongue was rolling with mine. The lovely touch of a woman was new to me. I was still a virgin having never entered a girl. Now I considered my life as a woman. Her loving was pbeautiful and I relaxed into her arms as we kissed for several minutes.

“Ohh dear, Ms. ”

I weakly tired to push back and breathe but her kisses continued as her hands pulled my blouse out from my skirt. She was adept at this fast seduction for her finger now slipped the clasp of my bra loose as her fingers tweeted my nipples.

I paused her tongue.

“But Miss Sumner I need to explain, ” but her kiss stopped me again.

It felt amazing to be with her but I wanted to tell her of my gender shift. Then the door swung open and he stood there with his camera in his hand.

The moment was done. I was being held and kissed by my teacher.

He spoke with a chuckle.

“I wonder how you’ll explain this Ms. Sumner.”

He closed the door slowly behind himself as he stepped inside the small office.

“Has Mic here told you that she has a dick?”

I tried to fix my blouse as he said this and I saw her face contort.

“A what?”

Ms. Sumner moved me aside and started toward him.

“Ah, no no, Ms. Sumner. I have a picture and your position is at risk. Michaela here is really a boy aren’t you Mic?”

I was crying softly as she turned back to me. She looked in total shock.

“That, that can’t be you selfish prick, get out of my office now!”

I saw that he might try and ruin her career so I reached to her as I told her the truth.

“I, I am,” I hesitated a moment,

“I was a boy but I am no longer Cheryl. I’m transitioning. I don’t want him to report you.”

He snickered, “Cheryl, on a first name basis. My recording is still running.”

I felt trapped in the small space and he was threatening my new lover, my female lover. I decided to protect her.

“Let me go with him Cheryl. I’ll make certain he destroys the image and recording.”

She came to my side and held me briefly before I moved passed toward the door.

“Is it true? You have a penis Michaela?”

She said this, as she was now right next to me.

I turned and spoke softly, “Yes but I need to attend to him now Ms. Sumner or he may ruin everything.”

I took his hand and walked him out the office and down the hall. As I lead him to a corner I realized what I had to do.

“Look, you can’t do this to me, to her. I can’t allow you to. I want you to give me the phone.”

“Why would I do as you want Mic?”

I had decided to get the damn phone at any cost so I reached toward him and cup his cock.

“Because you want me to suck you off that’s why.”

I bent to one knee as he considered his phone. He looked at me and I licked my lips. I moved slowly down, onto my knees.

With my hand on his zipper I forced a smile up to his eyes.

“Well big boy give me the phone.” I extended my hand toward him.

He handed it to me while I pulled the zip of his jeans down. I saw the out-of-focus image and quickly deleted it. I then reached into his pants to grasp the first penis in my life other then my own as I flipped the recording to erase it.

“I’ll just check to confirm it’s clear,” I said as I looked at his hard dick bouncing near my nose.

I considered that I might be able to get away now that the evidence was no longer on his phone but I was in a comprising position.

I hadn’t thought of sucking a cock. But some girls suck dick. Way before I began my hormone therapy I was attracted only to girls. Now I had to put up or possibly take a beating.

My mouth opened as I closed my eyes and he pushed is penis into my open mouth. I felt it my tongue and then the back near the opening of my throat.

“Hey Mic, watch the teeth,” he said softly without menace.

At that moment I could have just bit him but something else occurred. I realized that I liked the control I held over him. The feeling of his penis, the head and the smooth shaft was slipping slowly in and out. I wasn’t aroused but there was a strong sense of power over him doing the act. Fellating him was better than I could have imagined. He had brought me off almost a month ago and I needed to defend Cheryl now for I wanted her to kiss me again.

I was on my bare knees on the cool stone and allowed him to fuck my mouth. Like most guys though he lasted only a minute before he shot into my throat. The taste of semen was new to me. Its saltiness was okay. I might not need to shallow any cum for the rest of my life but I did that day. His load was not large and I held him within my mouth to protect my makeup.

“Wow Mic, that was just awesome. I knew you’d be back. I hope you loved my juice.”

I stood and straighten my skirt, picked up my bag and walked away without looking to his face. I left him watching my ass. I felt amazing and feminine having given my first blowjob. Turning the corner I saw Cheryl.

As I approached the office she pulled her door closed she said, ” Let’s go for a drink.”

At my car she suggested that I drive.

“You did something quite special for me Michaela. I heard the whole thing. In fact I slipped close enough to snap a picture. We don’t know if he’ll try anything else but this may come in handy.”

I saw the picture as I glance quickly. I was licking his cock while on one knee; my skirt touching the floor and concealing one of my heels. My eyes were closed in the picture.

“It’s actually pretty erotic,” she said as her hand moved to touch my shoulder.

“I was surprised by your news but I’m still attracted to you Michaela.”

I drove along but my head was somewhere else. Having Cheryl near was good though.

Scene Two

The event in the darken parking lot and Cheryl’s office had made me realized that I had to accept that I needed a change. I completed my first semester of college and then left home. The trauma of dealing with my friends and acquaintances was too hard. I tried of explaining myself but I felt like a target for a group of boys who had known me for almost twenty years and now considered me theirs to abuse.

In late December I moved across the state to a larger town where I knew no one and could have a fresh start. I wanted to keep close with Cheryl but she was now three hours away.

It was my mom who thought it would help me.

“You have developed quite well Michaela. These months have been a trying time but the changes to your appearance due to the medicine, ”

I smirked and interrupted her, “Those pills are important but its not medicine mom.”

“But the affect is still clear. You will not have trouble with someone thinking you’re transitioning Mic. Your hair looks beautiful and full and you’ve learned to move and speak like a girl, ahh, I meant like a woman during these passed few months.”

She called me Mic instead of Michaela around the house. Her sister’s daughter was named Makayla and she shortened my new name.

“I am just saying, oh never mind.”

She was exasperated with me but she went to her room a minute. Returning with a small purse she extended it to me.

“I did save some money. I anticipated that you would choose to move away and the three thousand dollars should be helpful.”

The population of Akron was almost a quarter of a million and it was only forty minutes from the City. My first job interviews went well but after waiting a week I decided to take the job I was offered. I had wanted the job in the women’s section of the department store because of the employee discount they offered. The lady whom interviewed me suggested that something might open up but in two months. I had to accept the alternative.

The Big-box retailer didn’t pay as well but they didn’t ask many questions and they needed me to start immediately. I worked mostly the evening shift from three until closing at ten. I liked the work but I was on the floor most of the time. I was near petite but the job required some lifting. Moving the boxes wasn’t difficult due to the lifts the store used.

After a few weeks at the store the assistant manager made a pass at me. As he pushed me down to my knees in the back room I simply told him that I was a virgin. I didn’t want to have sex with him and looking at this second dick was revolting.

“A what?” he gasped.

He pulled me up from my knees and apologized.

“I had just assumed that you were another runaway with some sexual history!”

He zipped up his pants and was red-faced.

“I don’t want you to report my behavior so what can I do to help you Michaela?”

He was good to his word and offered to elevate my responsibilities.

“But what I need is better, or more normal hours Dan. The extra money will be good too.”

He suggested he could make that happen.

“So you will have a few more hours, maybe to full-time and a increased pay rate.”

The next week I was put on the day shift with an eighty-dollar a week increase. The adjusted pay was nearly as good as the department store.

A month later Dan noticed that my work production had increased and he moved me to the accounting office where I would work along side three other women. I was the youngest but the other three were all around thirty years old and they quickly became my girlfriends and advisers.

When I receive my next paycheck it was nearly two hundred dollars more than my initial check. I decided to speak with Dan. I felt somewhat guilty.

“No Michaela you have earned this position and the raise. The quality of your education is better than most of the girls we hire. I could see you within a year or two running that department. Listening and studying while you were in school created this opportunity for you, not my error in judgment.”

The best thing was that I was no longer on the retail floor and didn’t have customers grabbing my butt or worse. The hours allowed a normal schedule but in the evenings I was lonely. I spent my time furthering my french language skills that I was good at in high school. The DVD course was relatively easy to follow.

One Thursday afternoon the girl ahead of me in accounting asked me to go out with her to a bar after work on Friday. Tony had emigrated from Canada and spoke a bit of french. We would practice the language sometimes when we were alone at the office.

“Just bring a better dress and we’ll change in the locker room.”

I had worn a dress most days now that I wasn’t on the floor.

Can I go out dressed in this Tony?”

She looked at me.

“Ahh, maybe something a little more sexy Michaela.”

Arriving to change the next evening after my shift I was a few minutes behind Tony. I was surprised when I walked in and saw her. The difference in her appearance may have been all makeup but I got a little stiff looking at her.

“You look so glamorous Tony.”

Her long hair! I had never seen her this way since she worn it up at work.

“I know, the hair. I started wearing it up to stop the harassment out on the floor. The customers, even some of the women shoppers were hitting on me.”

Ten minutes later she had done my face and I was completely surprised by the results.

“I have never felt so beautiful Tony!”

We drove to the bar and Tony explained.

“I studied at a beauty academy for a few months but I couldn’t cut hair worth a damn. Thanks to my math skills there was an alternative.”

The Happy Hour was just getting crowded when we arrived and the Bouncer waved us passed without a cover charge. I followed Tony across the darken dance floor. She stopped at a table and looked around.

“I don’t see Cathy yet. She’ll find us, no worries.”

I moment later Tony stopped a waitress and ordered us a drink.

“Wine or beer Michaela?”

The girl smiled and stepped closer.

“I like that name, I’m Suzanne by the way.”

The woman was hitting on me!

I glanced at Tony who looked embarrassed.

“I’m sorry Suz, I forgot to introduce you.”

As Suzanne left to get the drinks Tony moved closer and whispered.

“She and I got together about a six months ago. She fucked me silly!”

I tried to restrain my grin as I considered what Tony had said. I hadn’t picked up on Tony’s sexual preference for girls.

I wondered now if she was trying to seduce me then she said, “I’ve been with both men and women on and off for the passed two years Michaela. We work together and therefore we shouldn’t become involved okay? Besides you’re probably not into girls.”

I smiled and didn’t reply immediately.

“Thanks for sharing with me. Your honesty is why we’re becoming friends and I need some of both.”

Suzanne came over carrying the tray of drinks.

“Michaela’s is special just as she is,” and after she placed Tony’s down she whirled about and kissed my cheek.

“I can’t wait to fill your next order sweetie,” Suzanne said as she ran her finger along my exposed leg as she walked to the next table.

Tony told me that this wasn’t a lesbian bar but a true gay friendly establishment.

“Suzanne likes more submissive chicks. You might have fun with her.”

I wondered if I was that obviously passive.

“How can you tell that I’m submissive?”

She told me that it was okay to be queer for girls and that most of her friends could be described as acquiescent at sometime.

“I like girls Michaela and I sometimes end up with a woman who pushes my buttons. I’ll crawl to her, or anything to get into her bed. The right girl can get me to do whatsoever she wants. I love to play games too.”

Each time she could Suzanne came over to our spot.

“So Tony, have I got a shot with your new friend? Will I be giving her a ride tonight?”

Tony pulled her into a whisper as Suzanne looked at me, “Really?”

Then Suzanne came close, took my hands into hers and placed them on her breasts.

“Kiss me Michaela”

I did and she opened her mouth as I did and her tongue played with mine. Our kiss was quite passionate. I released slightly into my panty.

As our lips parted her hand touched the inside of my thigh but didn’t probe any further.

“I get off at one tonight. Please hang for me Okay?”

I was breathing heavily. One more kiss like that and I would blow into my thong. Her lips were so exquisite moving across mine. The kiss was so sensual. The girls I had petted with back in high school never caused me to loose it like Suzanne had just now.

I demurely smiled and Tony giggled, “I think she’ll be waiting Suz.”

A few minutes after nine Tony’s friend Cathy arrived. Her smile was so beautiful. I was attracted to her immediately but she had a man with her.

“This is George. He works near me and we’re friends.”

George was checking out Tony. I saw him look at her large bust and wished the hormones had helped me develop a larger chest. My near b-cup breasts were perfect most of the time but seeing him lusting made me envious of Tony’s breasts.

After Suzanne brought my third glass of wine I saw a guy looking directly at me. A few minutes later the tall brown skinned man walked over and asked me to dance.

Tony saw me considering a rejection but spoke, “Michaela go on. What’s your name big boy?”

He was a bit startled, “Ah, what, oh I’m Keith miss. Michaela is a beautiful name.”

I am quite small for a transfemme at barely sixty-five inches tall and under a hundred and twenty pounds. Keith was huge standing next me even with me in three-inch heels. He extended his powerful hand and gently moved me into the crowd on the dance floor. After three different songs I asked Keith if we could pause.

“I need a rest too Michaela. What white wine were you drinking?”

We moved to a table opposite the girls and as he stepped away for the drinks I looked across and saw Tony wink at me. I hadn’t seen Suzanne in twenty minutes and was still swooning from her flirting. I looked over the crowd and the scene. There was a lot going on. I saw Cathy standing nearby talking with two girls who were clearly overdressed. She had her hand on the shorter girls bottom and a moment later I watched her kiss the woman.

I hadn’t expected to meet Tony’s friends. She didn’t speak of them but I was glad to see Cathy with this girl necking. My own sexuality was unsettled though a man and a woman were after me tonight. I hadn’t ever had sex with a girl before starting the hormones and now I sensed something as I watched the women kissing.

Keith came back with two glasses of wine.

“I liked your selection and got a glass of it for myself as well,” he sipped the wine.

“Refreshing after the dancing!”

I listened to Keith talk. He was attractive but I was new to this. I wondered if I could sleep with a man. He was big and powerful and I had felt his penis when we were close. Realizing that I had caused his excitement made me smile.

“What?” he said when he saw my grin.

“Nothing, it’s just fun to be here tonight.”

Back home the boys had mistreated and insulted me but Keith was treating me like a lady. I wasn’t planning to sleep with anyone so I decided to keep my gender history to myself. I liked having this big strong man nearby though. His attention made me feel sexy but my thong was damp due to Suzanne’s kisses.

“I love really feminine girls Michaela. You’ve attracted me by your subtle manner and smile.”

An hour later I realized I hadn’t eaten and decided to ask Tony if we should be leaving. When Keith went to the restroom I walked over to her.

“I think we should get some food. He likes you?”

I shifted about on my sore feet.

“I think so but I’m tried and he isn’t going to get into my panties tonight.”

Cathy finally approached our table and Tony introduced us. Cathy was tall and in heels she almost was Keith’s height. Her dress wasn’t revealing but it expressed her narrow waist and perfect breasts. This woman knew how to present herself. I was more than a little jealous of her long blonde hair. When her girlfriend approached Cathy kissed her and I squirmed as my body responded.

Tony told her we might be heading home.

“Michaela’s first night out has been interesting. Suzanne is after her as is a beautiful brown guy.”

Cathy then moved beside my stool.

“This evening was too short Michaela. I too like girls and boys. Tony will find a way to get you out again soon I hope.”

She moved to the dance floor with the short girl tight beside her.

“Cathy will get that one home tonight and teach her a thing or two.”

I wondered what Tony meant by this.

Then she looked at me.

“What about Suzanne?”

I looked across the floor and saw her talking with a guy with long hair in a ponytail seated at the Bar.

“How do I politely ask for a rain check?”

Keith came back and saw that I had moved. He came over to the table.

“I could get something to eat girls. Can I buy you a simple dinner? There’s a Diner down the street.”

Tony answered for us.

“Only if we drive. You’re thinking of the Talk Diner right? My feet need a rest and though it’s only a few blocks let’s drive Keith.”

As we approached the door Suzanne came to my side and palmed me her card.

“Sometime real soon honey okay?”

After dinner Keith gave me his number too. I was so new to this I almost forgot that I should reciprocate. I liked him but wanted to go slow. Having a man be nice to me was surprising but I was withholding something and I was unsure how to go about explaining my history. I was simply happy to be out without being insulted.

“I’m sorry, mine is 533-6861 Keith. Thank you for the dinner.”

Back in Tony’s car she asked about the evening, “Well does he get you excited?”

I sensed she had more on her mind and I resisted sharing. Three things had occurred that caused me excitement. Suzanne causing me to nearly climax with her tongue, watching Cathy making out with the short blond girl and Keith’s stiff penis rubbing against my thigh.

I bit my lip.

“Well he’s a good looking man. I had never considered that a black man would find me attractive, you know?”

She smiled, “Why the hell not? You’re a beauty and tonight’s makeup made you look sexy Michaela.”

I smiled back and said, “You know for the first time I actually felt sexy Tony.”

As she drove back to the store we talked of next weekend. She had a Saturday shift tomorrow.

“I want to take you to another place next Friday. It’s more up my alley and we’ll need to be a bit more dressed. After work we’ll get some take-out and then dress to the Club okay?”

The following week was pretty typical. I had been working and living away for six weeks and every other night mom would call. I had also spoken with Keith. He had asked me out but I suggested the following week, maybe on a Thursday evening.

“I’d like to take you to a dinner place I like Michaela. Actually that is better, the following Thursday. Ten days okay? I have to go out of town next weekend to see my mother.”

I had made a date!

On Wednesday Tony asked about what I would wear to the club. Anticipating the Friday evening I had been shopping and found a sexy club dress. I showed her a picture from my phone.

“Perfect! You’ll make an impression in that babe.”

I had bought some silver sandal heels as well.

“Are these too much?” The heel was nearly four inches.

Tony just smiled.

“I’ll help with your hair too Michaela.”

“I thought you didn’t do hair?”

She frowned, “I learned a few things at the Academy!”

At Tony’s apartment we each showered. She had a two bedroom with a second bath as well. I discretely tucked my small penis and testes in the thong and pulled the sexy nude sheer pantyhose up over my hips. I heard a soft tap on the door.

“Let’s do your hair Michaela.”

Thirty minutes later I saw a girl looking back from the reflection.

“Wow. Tony you’re amazing for a dropout!”

In her Jetta we drove the few miles to the Club.

“Don’t be surprised by the number of women you will see here. It’s a good mix of queer and straight and others. The music is amazing and we’re dressed for a ball.”

In the parking lot she stopped me.

“I’ve got you something. It will let you control this evenings rituals.”

It was a silver neck choker. She positioned it and clicked the catch.

“There will be a lot of girls after you Michaela. This will restrict the intensity of their come-ons. It indicates that you are ‘taken’ though we both know you are not okay?”

I nodded my understanding and with the silver necklace clip into place and matching my tall heels we strode to the door. Tony handed the female bouncer two twenties. The bouncer smirked as Tony took my hand and led me through the doors.

My eyes adjusted to the darken space. A mirrored ball spun and the music was loud. I saw hundreds of women in the large room. There were some men too. No one seemed to pause as we entered and Tony kept me close as we moved to a booth. I saw Cathy and she had the short girl by her side from last Friday though her hair was now quite dark. I was self-conscious about these tall heels. When we were standing at her table I saw Cathy notice my necklace. She smiled at Tony and turned to kiss the girl beside her.

As I looked about I saw that there were groups of men but they seemed to favor each other. There were a few mixed couples; at least I’d assumed them to be.

Cathy stepped away and when she returned she sat beside me.

“I like your dress Michaela. Actually I noticed the choker but we both know you want to be with me.”

I was close to her as I felt her hand on my thigh.

“Hey Cat remember she came with me okay?” Tony frowned slightly.

Cathy pushed against my hip.

“Tonight I will tease you Michaela. I want to make your little cunny hunger for my tongue.” She turned my face and kissed me intimately.

“That will keep you focused,” she said.

She stood and moved next to the short girl pulling her to stand. I was dumbfounded. Why I hadn’t told her to ‘stay back’ I’ll never know.

Tony smiled and reached to take my hand. I was flustered by Cathy and she tried to calm me.

Just then Cathy came back with Monica.

“Watch Michaela. I will play with Monica as we dance,” she glanced at the short girl who seemed ready to cry. I watched as the two started to dance.

There were several other couples dancing provocatively but Cathy had seen my lust and she had felt my tongue respond. I was tense watching her move about and then I saw her as she lifted Monica’s the dress exposing her nakedness.

Tony moved closer.

“She told me she would get your attention tonight but I didn’t think this would be how.”

The two danced quite near our table and Cathy was kissing her lover as it appeared that she was rubbing the girl’s pussy beneath her dress. I was taken aback seeing several other couples nearly copulating on the dance floor nearby.

Tony was still close and whispered to me, “I told you I wouldn’t violate our trust but you’re a very sexy girl Michaela and I’d be lying to say I wasn’t attracted to you.”

We both looked into each other’s eyes. I didn’t want her to misread me so I said, “I appreciate your attention and help Tony but I’m not into you. Please understand.”

She reached and hugged me.

“That’s the way it will be,” Tony sighed.

“Cathy will get another girlfriend from me.” She smiled and taking my right hand kissed it softly.

After her brief attempt she told me about how she had slept with the short girl, Monica, some weeks earlier.

“Cathy seduced Monica much like she is doing to you.”

I looked at Monica who seemed entrance just then.

“She made her dye her hair for god sake. Cathy is a great lover of women but she can be too much.”

We watched the dancers and talked for twenty minutes.

Cathy came to the table and extended her hand, “Come with me Michaela.”

I looked her up and down. She was wearing quite tall nude toned heels. I worried if I could dance in my own heels. To be spinning and dancing in them would be a challenge. Her dress had a flowing but short hem with a deep plunge neckline; I didn’t see a bra as I studied her breasts. I wanted to be with her. Her long hair was up in a knot but still extended down her back. I smiled at her as I took in the details of her sexy body. I was aroused as she pulled my hand and we kissed again.

“I’m glad you want me Michaela. There are others who want to take you home. I will be less overt with you since we have only started to play but I think you will be mine soon.”

Once on the dance floor I saw many other couples passionately dancing. Cathy was leading me and she looked wonderful. This woman wanted me and I felt special.

“Dancing with a beautiful girl gets me so hot,” she said as she moved close and kissed me with her body against mine.

Another couple moved too near and bumped into Cathy causing her to almost fall. Somehow between the four of us we stopped her from hitting the floor. She giggled softly and took my hand.

“I need to rest Michaela. You are officially off the hook for the night.”

I helped her back to the seat but Tony wasn’t there. I wasn’t comfortable making small talk with this serious beauty. She was rubbing her right foot, which was set on the seat immediately beside me.

Without thinking I moved her hand and began a massage.

“Caressing me at last Michaela. That feels nice. You have good fingers. Owwh.”

I smiled and said, “My mother was a trained masseuse. I learned a few things from her.”

“But you have strong hands for a girl.” I paused as she took my left hand.

“And they are actually small too.”

I continued to work on her sore foot.

“You know I wanted to take you home tonight. The collar was my idea.”

I looked at her and paused the massage of her foot.

“I need more time. I haven’t been with a woman Cathy.”

I looked over at Monica sitting still. She was almost to tears.

It was crazy that I was attracted to such a strong lesbian. It was both her manner and her looks and Cathy knew how to use both. I wanted her to fuck me but I was a virgin, having never penetrated a girl. Now I was a girl to Cathy and I wondered how I would resolve the next step.

I decided to be shy and quiet as she turned my face to look at me. I looked down and whispered, “I’m a virgin Cathy.”

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.

After I dried I looked at the garments. I had never worn a garter belt and it took a few attempts to settle and clip it on my hips. I had seen stockings being attached but had never actually attached one. After three attempts I got the white silk to stay with the brass clasps. The small white satin brassiere and lace thong lingerie seemed very expensive and fit perfectly. A pulled the thong up and tucked my tiny penis back. A saw she had left a pair of tall white platform heels out. They were similar to those the actress Jenna had on in the movie. I wondered if I could walk in them. The heel was at least six inches tall but with platforms.

I looked about her bedroom. All of the furnishings were white with the bed coverlet a soft gold weave. The drapery was drawn and I felt excite as I saw myself in the tall mirror.

“Where are you Michaela?” she called out.

I stepped slowly through the wide door. I saw her on the sofa with her legs up and under her. Two glasses of wine were on the table. Cathy had changed into a gold gown and heels. Her makeup seemed sexy and sultry.

“You looked perfect Michaela. My present has arrived. Come watch Jenna get fucked with me dear.”

I stepped between the screen and the sofa and saw Cathy push her fingers beneath her gown.

She rubbed her naked pussy while looking at me.

“You look remarkable. Here, let me put this pearl choker on you.”

“I almost want to call you Jenna but that would be unfair to both her and you.”

I turned my back to her, the thin panel of the thong riding up my cleft, as the movie began again.

“That’s a correct outfit for a special virgin. Come to me.”

I was so anxious. I should have found a moment to tell her. Then she stood and we kissed. Our tongues played and I felt my penis begin to stiffen. Her hand dropped to rub my mons. With the tall heels we were the same height.

“Cathy, ahh, I should have, ”

I moaned softly and couldn’t speak. Her teasing of my breasts was amazing. I was aroused being nearly naked with Cathy.

“Shh , Michaela, shh, ”

Her leg moved between my thighs as her fingers played with my nipples through the lace of the brasserie. As she pushed her tongue inside the bra cup her finger exposed my right breast. Her right leg was lightly banging on my pubis.

“The heels are sexy Michaela.”

She moved upward and again she kissed me while her fingers caressed my nipple.

“You have noticed how petite Jenna is and her breasts are just like yours, pert and beautiful.”

She kissed and caressed my left nipple, “I want you.”

She continued but her right hand dropped to caress my bottom. She stopped though and I thought she might have felt my tucked penis but she moved back half a step.

“Walk for me. I want to see you and Jenna together. I’ve been waiting for a long time to find a lover as unique as you. I want to relish this evening.”

I walked slowly to prevent banging the table and upsetting the wine wondering about her comment. I began to move with the music from the Jenna scene as she danced for her lover as well. I saw Jenna pause so I stood in front of Cathy. She came to me and we held each other and kissed gently.

“Why are you trembling? We have all night Honey.”

Her fingers were again on my bottom as she kissed me. I knew she would find my tiny prick in a moment so I took her arms and moved them about my waist. She moved back slightly. She was looking at me as her finger slid down my belly to the top of my thong. A moment later she moved over my mons and her long fingers slid into my thong. She felt the stiffening little cock.

I didn’t know what to expect but she clearly did.

“That’s what I had hoped to find between your legs Michaela. You’re quite a Lady but somehow I knew you had more than a pussy here.”

Her smile didn’t change as she bent down to look at my body. I moaned as her fingers held me. I was happily dumbfounded.

“Cathy, I should have told you,”

“Well no,” she said. “You shouldn’t have to defend your needs or prepare someone who wants to sleep with you.”

“But I ”

“Michaela, I chose you and it’s on me. Look at this glorious little cock!”

She moved her face and kissed the tip of my penis.

“I saw a bit of a bump, ummh that first Friday, when Tony brought you to the bar. We met and I saw your long neck.”

She stood and ran her fingers along my neck and throat.

“From then on I have studied your movement and your other features. It takes a lot to be a woman doesn’t it? We are trained when are we are little to sit, stand, move certain ways and say things that boys don’t. I was certain when you arrived with the choker last week that I had read your sexuality.”

Her kisses were now quite focused on my neck and breasts since she had pushed the cups down exposing my tits.

“Your breast development has caused your clit to shrink. I like that it’s cute and small.”

Her fingers reached down and grasped my hardness. I was surprised by the size my penis had grown to.

She dropped to her knees in front of me. I could see the image in the mirror of the porn actress voguing on the screen as Cathy moved the panel of my panty aside and kissed my now stiff penis.

“But how can you want me? I thought you were into girls.”

“And what do you think you are Michaela? You are certainly not a boy!”

Her loving tongue and mouth stirred me and my penis got stiffer.

“Good thing this still works Michaela. I want it in my cunt tonight. Shit, I may never let you leave!”

I saw the actress Jenna turning with her lips sending kisses to the camera but Cathy paused the action. She stood and walked to the bedroom.

“I forgot the star of our show Michaela. We need a cock for you to loss your virginity.”

Returning I saw she held a black toy with a strap in one hand and shiny dildo vibrator in her other.

“Meet your invader Honey!”

I watched as she stepped into the harness and settled her dark cock on her mons. A moment later the movie was showing a second person, a brown skinned actor with a very hard cock.

“He gets Jenna and I get you! My stiff dick wants you so badly Michaela but since you’ve never allowed any boys in here,”

She bent and turned my hips to kiss my rose. Her tongue licked there for some moments while I felt her hand on my hip. Her tongue at first stayed at my rim but I could feel her licking as her tongue darted into me.

“Oh my god Cathy!”

I had never felt this before. She was fucking my tight hole.

“I’ll play with the slim toy and we’ll see how eager you become.”

Her thumb now rested on my tight hole but moved across the rippled skin.

“Don’t be frightened Michaela. We will take however long. I want to be your first lover and will not cause you pain.”

The thumb had slowly entered my bottom.

“The muscle just needs to be loved dear.”

She paused and I saw her face was moist. Cathy moved away a moment back on her knees.

“Look at me Michaela. I need your attention Honey,”

Cathy stood and moved toward Jenna on the screen and her faux cock at her hips wiggled back and forth just as the guy’s in the movie did.

I was mesmerized by the scene, both in the room and on the screen. I had never imagined I would want to let someone in my butt. I was a girl but I hadn’t been sexual other than masturbating to my lesbian porn. In those fantasies I was with another woman. We would rubbed and lick, kissing each other. Eating pussy was my fantasy not penetration. Somehow my new girlfriend had seen through all of me and now she was about to take me on her adventure.

“Don’t be a chicken Honey. This is a small sized cocktoy. It will easily slide into your fresh bottom!”

I heard the soft buzz from her toy and turned my butt toward the screen and Cathy.

She hummed along with the toy, “Your magnificent butt is all mine!”

Her one hand was running up and down the shaft at her hips while I watched her and Jenna.

“But I need you to help me. I need my black cock sucked. Have you ever sucked a cock Michaela?”

She stepped toward the sofa and sat down. The rocket shaped thing stood tall above her hips. I couldn’t speak.

“On your knees Honey. This thing needs your mouth.”

I felt so aroused as my stiff clit remained drawn back partial held by my thong. Cathy’s smile and her sense of command made me comfortable and I bent to my knees. I could still see her film and Jenna was subtlety kissing the head of the penis. Tentatively my tongue reached to kiss her faux cock.

“She will show you. Jenna will allow me to fuck your mouth Michaela. I sent that Monica packing because she wasn’t adventuresome. I get the feeling you’ll enjoy being my lover.”

I spied the action of Jenna as she took just a bit of the penis into her mouth.

“That’s a girl, slowly love my cock. Remember my pussy is at the base and I can feel your loving lips Honey.”

I hadn’t ever considered that I would be doing this, sucking a strap-on with a female lover. That I was with a woman made it even more outstanding. She gently ran her fingers through my hair and cooed.

“That my girl. Take a little more into your sweet lips. I’m getting aroused watching you and Jenna suck black dick.”

She was panting as she neared climax, “No, now stop. I don’t want to orgasm yet.”

I saw that Jenna was now straddling the man’s lap as his big cock reached her butt hole.

“She loves a big cock in her ass Michaela. I think if I’m gentle you will as well. Let me play with you.”

She positioned me on the table on my knees as she licked my bottom. The thong was soaked as she pushed it aside and her tongue entered me.

“Oh damn Cathy, you are going to make me explode,” I moaned.

The feeling of her war tongue licking my ass was amazing and startling. I felt the opening soften as I relaxed under her tongue.

“I like how smooth you are Michaela.”

I felt the warm metal object at my butt as Cathy licked and slid her shiny tipped toy back and forth across my tight hole and butt.

“Oh, Cathy,”

Just then I felt her push her long finger into me and I moaned softly.

“This will take some time but I’m a patient lover,” she pushed the thumb deep into my bottom.

She moved onto the low table and her finger was removed for a moment. Now facing me with my penis pushing against her belly she entered me again with her thumb.

Her kisses paused, “Now we’ll get another inside you. Just relax and I’ll enter your body Honey.”

The two fingers slipped into me and I held her tightly as the anxiety passed.

“That’s it Michaela, I won’t hurt you.”

After a few moments she bent and took hold of the vibrator. With the narrow metal tip she played across my taut rose skin. As she kissed me intensely she entered me with her toy, the subtle vibrations aiding the movement. She didn’t push deeply inside me but her kisses and the toys stimulation began to bring me off.

It wasn’t a rush but the slow action and her kisses together with my penis rubbing against her belly brought on my orgasm.

“Shoot onto me Michaela!”

She was panting with me, “This is amazing!”

She held me about the waist and kissed me while her other hand fucked me with the metal tipped cock.

“You were filled with juice Michaela!”

I began to collapse from the ejaculation but she held me and we kissed. My penis again became small but our skin was covered with the sticky semen.

“That’s a first for both of us,” she whispered.

As she held me she kissed my closed eyes and then bent to my breasts. I felt her left fingers on my tummy gathering some of the seed.

As she licked my cum she whispered, “This will be difficult to repeat so I’m going to enjoy it Michaela.”

She pushed her fingers into my mouth and I tasted my juice for the first time.

“Yeah, you are a girl but with this extra special toy.”

Scene Five

She returned from the Kitchen with a warm wash and we cleaned up from our first sex play. Her movie was paused.

“Wait until you see the next part Honey!”

The wine was still cool and we sat together on the sofa.

“You haven’t had sex with anyone else, really Michaela?”

I told her about my teacher Cheryl and the petting and kissing with my earlier girlfriends.

I was holding her vibrator, “Does this count? Am I still a virgin?”

She still had the strap-on about her hips. Her hand took mine.

“This will be your first fuck. Then you will no longer be a virgin. It’s just a bit thicker.”

She told me about her previous relationship.

“Christie is a OBGYN and we were lovers for several years. She returned to her marriage though.”

“Was she your doctor then?”

She giggled, “No, we met at a friend’s party and she cornered me in the hall. She wasn’t a true dominant since we weren’t into the typical routine but she definitely topped me.”

“Did you use these toys with her?” I asked still holding the vibrator and looking to her crotch.

“No silly. I got these this week just for us to share but I have many ‘retired’ ones. Not really a collection but several have great memories.”

“Did Christie fuck you only in your pussy?” I reached to stroke the black toy between her legs as I moved to kiss her.

We kissed for sometime but she paused and told me about her bottom without missing a beat in the conversation.

“No she introduced me to anal almost immediately. In fact she had her finger in my bottom in the Powder Room that first night. The next day I went to her office and between her appointments we made love the first time.”

I squeezed the shaft of her cock. It was some material I hadn’t ever encountered. It felt like skin though it was fake.

“She licked my ass that first time and I fell in love. No one had ever kissed me like that.”

I smiled, “Yeah now I know how you felt. Your tongue was wonderful.”

“Did the toy hurt you Michaela?”

I looked at her as I played with my hair, “No Cathy. It was surprising, but as you said, it’s small and thin.”

I was anticipating her next move and wanted to tease a bit.

“Are you going to fuck me Cathy?”

She pushed the ‘play’ button the sex sounds started, moaning and soft breathing.

“Yes I am, just like he is going to stuff his black dick into Jenna, I will fuck you Michaela.”

I turned to see the girl now licking her man. I bent to take Cathy’s toy into my mouth.

“Can you see her Honey?”

I nodded and continued.

Jenna sucked for a long time and therefore so did I. Cathy encouraging me. I tried to mimic Jenna’s twisting hand-work about her lovers cock.

“That’s it, sucking cock takes practice. Remember to cover your teeth Michaela.”

I saw Jenna using her hand to pump the wet penis so I did the same. When the man stood I dropped to my knees as Cathy stood in her heels. The cock in Jenna’s mouth was much larger than Cathy’s.

The man pushed Jenna to an ottoman and stood behind her as he played the tip of his cock across her tight back hole.

“I’m ready to fuck you Michaela. My cock wants you. The sucking brought me close to cuming Honey.”

I felt her spread a cool lube across my ass cleft and then her toy touched me.

“You are ready, moist and hot!”

I looked back at her and cried softly.

“No Michaela, you will be fine”

Cathy pushed a small part her cock into me. It hurt and I moaned as tears formed.

“Oh yes, the head, breath for me, ”

As she paused with just the helmet in me I relaxed and the pain diminished. I saw Jenna bouncing on her lover’s thick cock.

“Yes, take some more of my black cock Honey.”

I did and I closed my eyes as she slipped into me another inch. My head was on the table and my butt up in the air.

“In this position it doesn’t hurt Cathy.”

Cathy hadn’t moved as I became comfortable then she moved very slowly out and then back into me. On the second thrust I felt the toy slip out.

“Perfect” she whispered.

A second later the cock was in me again and Cathy moved deeper and it didn’t hurt as much.

“We all need time. Going slow is actually best though.”

I was panting as she pushed further into my ‘pussy’.

“Michaela that is what I’ll call your hole from now forward. I can see the rim opening to my cock. I love being inside you. The end of the cock is banging on my clit.”

I looked to the screen and saw Jenna. She moved forward and the dick fell from her ass. Then she shifted to her back. Cathy moved me at that moment, exactly the same.

“Lift your legs high,”

This exposed my pussy to her cock. I closed my eyes as she re-entered my body but this time it didn’t hurt as she pushed inside deeply. In this position she could move more easily and my body began to enjoy the penetration.

“Some girls cum more readily with a cock in their ass,” Cathy said.

I was silent and with closed eyes I began to feel my climax start. I noticed that my penis was semi-hard. Cathy held my knees and continued to fuck me.

I glanced to her face, her eyes were shut now and the thin cocktoy was now moving rapidly in and out of me. The feeling deep inside was marvelous now. I rested my heels on her shoulder and held my butt cheeks. I touched my penis with my right hand as she increased her pace.

“I’m going to ”

Her breathing was sharp and I now squeezed the shaft with my muscles. I again touched my penis and I exploded.

“Oh my god Cathy!”

“Oh, hold on Michaela, I’m so close.”

I felt the semen on my fingers as her cock kept plunging into me. Some of my cum seeped down and the cock seemed to slip easier. Her fingers were holding the dark shaft close to her pubis.

“Oh, oh yes, oh god yes, ”

She screamed as her cock slipped out and I saw her fingers playing at her pussy.

“Oh my, ”

Then she was quiet and she fell forward between my legs to my chest as I reached to hold us together. I held her there for some minutes aware that my life was now so different. The gooey seed covered both of us and Cathy seemed to sleep for a few minutes as I considered the sexuality of my new lover. Could I really be with her and enjoy her crazy world?

Jenna was still being fucked but just then I saw the cock pulled from her and she shifted to suck the man. She relished the big dick that had fucked her bottom. I could not imagine that. I felt Cathy stir.

“That’s my favorite part of this scene. Her love of ”

“But what of the, you know, poo?”

She hugged me, “Soon you will know why she can lick his dick after it was in her butt.”

We both watched as the man erupted and flooded Jenna’s mouth. Cathy stopped the movie.

“We’re done with Jenna for tonight. Let’s get into bed Honey. We can shower in the morning.”

I hugged her, “Did I do okay Cathy, I mean for the first time?”

She kissed me and then unfastened the strap, “Yes, you are no longer a virgin Michaela. And I loved every fucking minute of it!”

As I settled in the large bed cuddling my lover I thought of the joy in my heart.

“You can stay with me tomorrow please?”

It was a question not a command and I shock my head yes.

“I can’t explain it Michaela but I feel so comfortable with you here in my bed, as if something has changed me.”

She kissed me and laid her head on my chest.

The sticky semen covered both of us.

“I like that you were so ready for me Michaela. You needed to be here. I needed you here.”

I smiled and reached to her pussy, “I hope you can enjoy me tomorrow here too Cathy.”

She kissed me as my fingers played along her slit.

“Tomorrow we will put you there Honey.”

Cathy was soon asleep but I remained awake for some time. This woman had somehow guessed my gender. Did Tony know as well? Cathy had planned this evening carefully. The home was set up anticipating my visit. She had decided to find a way to get me to come home with her.