Watching Jenna Ch. 02

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Florence said, "It is somewhat true Jamey. I have learned a thing or two from this sexy skinny bitch. What Celone would like is that you too could learn from Jenna."

I sensed that Flo was implying that her sister wanted me to receive anally and though I had once it was not enjoyable. I became nervous and Flo detected this.

"No commitment Jamey, just watch her," Celone said. "She can take small and large cocks into her ass but we love how she dances as well."

I considered them both but was still anxious. Celone moved closer and took my face in her hands and turned me so she could kiss me.

"You are a bit taller than Jenna but your diet has reduced your tummy. The Jenna movies will help you with this Jamey. I hope you can keep an open mind and enjoy her films."

Ninety minutes later I had watched them both masturbate as Jenna took a big black guys dick into her bottom. It did amaze me. Midway through the clip Celone had produced a small plug and pushed it into her bottom.

"These can help Jamey. We have a collection just for your training. Flo will get one after the show and demonstrate for you how it can be good."

After the movie we moved to the Kitchen for some wine and Florence disappeared for a minute and returned holding a velvet lined Plexiglas box. Inside were five different anal plugs. There was an engraved plate on the side. It said 'Jamey's Toys'.

"We don't share these generally Jamey so Celone had this prepared for you the other day on her trip," Florence said handing the box to me.

I looked a bit perplexed but they both came to me. Celone's hand slipped beneath my dress and caressed my bottom for I was wearing a thong to restrain my penis. Florence pulled me into a kiss. The sensual existence I had fallen into still astonished me.

"So this is another step sisters?" I moaned as their hands caressed me.

I couldn't imagine how I would accommodate these various toys but deep down I knew I would allow them to educate me. Each of their desires had brought me some new consciousness and pleasure so I had to consent that this might be as well.

"It is, and we will do this together Jamey," said Celone as her finger played at my back rim.

Scene Ten

Each week the three of us would do something in town together but only after we had spent hours pampering each other. The awareness that they had shape me to their will was of no distress to me. I loved the carnal life we were sharing.

When the three of us were in town there was a stir since most of the Villagers were working folk.

While we shopped or lunched we heard many compliments about the clothes, the shoes and the bags but also comments regarding the risqué style of dress. I had become their fashion whore but I glowed with the warmth of my feminine family.

"This was much easier than I would have imaged Jamey," Celone said as we walked along window-shopping.

Florence hugged me close and I felt her breasts rubbed my faux pair.

"You were so willing," she said.

I paused in my four-inch black spiked heels on the sidewalk, "Well I think you put something in the wine that first day but if so I'm quite happy you did."

I kissed Florence and whispered, "When will you let my penis inside your pussy?"

She said, "Jamey you are as much a woman as me now so I don't need the stick when I'm with you in bed. But I could see being pregnant in say sixteen months. After we all travel to see mom in Singapore."

A woman walking by heard this and frowned, "Whores!"

Celone had been using the anal toys to penetrate my bottom for several days now but Florence only wanted me in her butt or mouth.

"So do you think I should schedule a visit with Doctor Albright Flo? I mean Jamey are you ready for a real rack?" Celone asked.

Florence answered for me as her and I had discussed this yesterday, "She wants this sister so yes."

On the ride home Celone saw her favorite dance club.

"Ladies tomorrow we will go dancing. I haven't seen Cathy in almost a month and she is always fun."

Florence agreed, "Jamey can wear her new dress."

Celone asked her sister, "What was Cathy's girlfriends name?"

Florence had not met the girl but recalled the woman's name, "Michaela".

They had helped me find several new outfits since my weight had dropped to one-thirty-four. With the new mini-corset Flo felt I could have a twenty-eight inch waist. Celone had ordered this special one from England for me.

That afternoon Florence helped me try the restrictive garment.

"It's a good fit and the quality is superb. Celone knows how to acquire beautiful things Jamey. How do you feel?"

I asked if the corset was fully secured.

"No only about fifty percent drawn in so far. I will tighten it two or three more times over the next thirty minutes which will allow you to be comfortable."

Near four the next afternoon she helped me slip the new little black dress on after getting the corset set. The waist adjustment was important for the slim bodycon fabric.

"Good, this dress looks very nice. Let's practice your face work okay Jamey. Take the dress off for now sweetie."

Awhile later Celone came in after I had re-dressed.

"Holy shit Jamey!"

Florence smiled, "She looks amazing huh Sis?"

Celone came and kissed me, "Girl come to my room now please."

Florence laughed as we walked away, "She just now finishes getting ready and you're going to eat her all up Celone?"

Celone closed the door softly as I stood near the bed. I had never felt so feminine. The underclothes were beautiful french lace with a narrow thong holding my balls away. The stockings Flo had given me were nude toned silk with an interesting enchained script up where the back seam might normally be. The new heels were almost too high but as Celone now rubbed my bottom they had the proper affect. I saw her attaching the strap-on to her hips. She was going to fuck my bottom for the first time.

"If we are going out I want you sated Jamey. I think we both know that my sister is in love with you. There will be girls and guys interested in you at the club and my girlfriend Cathy will definitely make a pass, I guarantee that."

She was wearing a silk robe lose about her and the white faux penis was glistening.

"We have allowed your opening the proper preparation Jamey. It is my joy to initiate you to my cock tonight."

I had moved to sit on the edge of her large bed. I had become unaware of the corset except for how different the hose' felt when held by the clasps attached to the lower edge of the taut garment. My black dress hem swept away to exposed the hose' and I saw the brass hoops holding the silk. As Celone moved closer I slipped to my knees and felt the tug of the stockings.

"Jamey, careful not to ruin the hose."

My deep red lips actually wanted to suck her dildo. I smiled up to her eyes as I considered the act I was keen to participate in. These past four weeks had so changed my reality and I wanted more. Celone stood close as I studied her toy cock.

Celone said, "I have wanted to fuck you from the moment I first saw you Jamey. Now you are ready and, "

The realskin dildo entered my mouth. It wasn't too big and my hand reached to hold Celone's bottom as she allowed me to lick at the head of her toy penis.

"you look good with my cock in your mouth sweetie."

As she held her penis toy she bent to reach across my corset covered back and her moistened finger grazed about my hole. I tried to focus on the dick in my mouth but I had to stop a moment.

"Celone, are you sure?"

The three times this week she had pushed the small anal plugs into my bottom. Each was different but the sensations the objects caused had me convinced I wanted what Celone had in mind for this evening.

"Suck my dick Jamey. Get me really wet because I'm going to be your first fuck."

Her finger had now entered my ass as I enjoyed the scent of her pussy. She was excited as well.

"You have me so gooey Jamey!"

I hadn't seen that Celone had one of my small plugs in her hand but as she removed her fingers the metal toy's wide base opened me as she began to insert it and I yelped.

"Oh my God, Celone!" I bit down on her fake dick but she only giggled.

"Girl, you need to be ready, and watch the teeth. You are about to lose this virgin opening. You are still tight. Think of something nice and soft."

I focused on her penis and the thought of Florence's bottom and the plug moved into place and sealed my hole.

"Much easier today Jamey and the biting wasn't nice."

As I continued to lick and suck on her faux prick my tongue moved along the lower side as I covered my teeth.

"Ahh, you are such a girl, that much better. Someday we will have to bring a warm cock home for you."

This thought didn't register in my brain at the time. Later she would come back to it.

"The dance club will be filled with both men and women ogling you tonight Jamey. I want your little dick to be empty and to stay tucked so maybe a tighter panty would be good.

I wasn't listening though. I was relishing the new activity and my eyes were closed, as I was no longer thinking of my genitals. I was a woman giving head, fellating her lover's cock. This was interrupted by her pulling the plug from my bottom.

"Now for the real dick, "

She removed her dick from my mouth and swung me about with my tummy at the bed edge.

"I want to watch this enter you butt. Reach back and pull your cheeks apart Jamey," as she pushed her stiff penis into me and I gasped.

"Ahh, Celone, please, ooh."

Though she was slow the first movement caused me to wince in pain. This was short lived, for it was a slim phallus and I my opening was moist from the lube on the plug. I still squeezed my eyes shut as she leaned over me and held my waist as she slowly pushed into my body.

"Celone, it does not hurt so badly now," I said as I nodded that it was fine.

"Then roll your hips slightly and do some of the work Jamey."

I did and she slipped in deeper.

"Yes baby, rolling on my cock," she began to withdraw as she moaned the words softly.

I turned to look at her as she smiled. Her fingers moved from my hip to my right falsie and she giggled realizing her error.

"We can remedy those in a few weeks Jamey. Then I'll have something to grab."

As she fucked my body slowly I concentrated on the penetration. Her anal penetration was now feeling good. She was only using a few inches of the six-inch cock but something was happening even though my penis was soft. The sensations were so different from my previous lovers. I wasn't the dominant player but the receiver and now I started to push onto her penis as she moved. The phallus went into me deeper on each thrust now and I felt the extraordinary pleasure rising within me.

"Oh Jamey this toy is going to make me cum," but she kept fucking me.

"Ahh, Jamey, I do hope that you are close," she was about to peak and though I was enjoying the dick that fucked me I wasn't near quite yet.

Her loud scream announced her orgasm as she pushed her phallus deep into my bottom. The toy must have hit my prostate for I immediately experienced my first prostate orgasm, intense, and I shot into my thong panty. I shook with this new sensation as Celone fell onto my back and moaned.

"Wow Jamey, you came as well huh?"

I was out of breathe and her cock was still in me. She held me across my back.

"Yes Celone, some how I climaxed but " I couldn't talk for I was still humming from the release.

"Oh Jamey, you had a girl orgasm huh?"

I didn't know what to make of this sexual event but I was certain I wanted more fucking and soon.

"I love that you are holding me after this Celone. You penis is still hard for me."

She giggled as she held me, "That's worth something right?"

Scene Eleven

After our sex play both Celone and I had showered as Florence set the meal out. I came to the Kitchen wearing the corset but without a thong. Tonight we had ordered a simple dinner. Florence had received the delivery and we enjoyed a Pinot while we re-dressed for the Club.

"She enjoying fucking you Jamey and I am quite pleased she did. I love making my sister happy," Florence said.

She reached and pushed my penis between my legs as she started to tighten the garment again.

"Now go and put on a thong. I want you little nuts back up in the hiding spot before we cinch this," she turned my hip and smiled. She kissed me.

The cab to the Club was the first time that I was dressed and out at night. The corset had settled and though I knew it was the structure making my figure feminine I just focused on the girls and the event ahead. The cab was a comfortable ride and I was between the sisters.

"The tones for makeup we use for nighttime are different Jamey," Flo said as she turned my face from side to side.

"There is even more drama by concentrating the darkest pigment on the lids."

I was lost in thought as she reviewed her work on my face.

"Now remember Jamey, we are all going home together, sisters tonight. No competition for the women okay?"

Celone said, "And no men tonight."

Celone took care of the cash so we waited while she paid the driver. I was swinging my eyes back and forth to take in the crowd of beautiful girls and their outfits. There were others there as well. Men.

"Jamey, looking is okay. Just don't flirt with them," Celone said as she took my hand.

As we crossed the dance floor I was glad Florence had insisted I change to the three-inch heels. I could see others weren't interested in the dancing for some women were in super platforms. My height with the shoes meant I was about average but Celone was much taller in her heels. She kept hold of my hand as Florence walked just behind.

"This is a good table. Flo stay here with Jamey a moment, I see Cathy at the Bar."

"Who is Cathy?" I asked but immediately remembered.

Florence smiled as her sister sauntered across the wood floor, "an old girlfriend. Crazy fun at times but like a fox."

I couldn't recall something Celone had said the other day about this friend of hers. It bothered me that she had rushed away but then I saw her and Cathy. The long hair of the tall beautiful woman was amazing and she moved so sensually on her heels as the two women approached.

"Jamey, please say hello to my good friend Cathy," as Celone stepped aside the woman came nearer and took my hand and kissed my fingers.

"So good of you to join our group Jamey."

Turning to Celone she said, "Yes it is remarkable. She looks lovey."

She seemed to be speaking of me.

Then Cathy looked back to me, "You have to meet my new lover Michaela. You two will share many things as you get acquainted. Florence you seemed to have found your mate hum?" Cathy said as she hugged and kissed Flo.

"Jamey is special to me Cathy and yes we are quite close," Florence had my hand and lifted it to kiss it.

"She has a special gift I see," said Cathy.

Florence now stood and moved to my hip, "Yes she does and she is mine Cathy."

Then I recalled the discussion about the Ladyboi's. I could see that Cathy had read me and she smiled as she came even closer.

"Yes Michaela will love to meet you Jamey. Your outfit is wonderful, the dress just short enough."

As Cathy's hand touched my waist I knew that she could feel the corset beneath the dress.

"Structure is important for our women Florence," Cathy said as she sat down beside Celone.

"Don't worry about me taking her away Florence. You have wanted to find her for years and I want your happiness. Oh, here is Michaela!"

Cathy stood and waved slightly to the beauty across the room. As she approached I saw the pearl necklace the woman wore about her neck. Her dress was a beautiful bias wrap in a deep red with thin straps. I noted her petite breasts for her nipples clearly pressed against the red fabric. Her tall silver sandals were sexy and she smiled as she saw her girlfriend. I saw her right thigh exposed as she took each wonderful step towards Cathy. She had only eyes for her lover.

As Cathy and her mate cheek kissed, Cathy introduced everyone. I was mesmerized by these lovers but quietly listened to the batter of the women.

"I met her about a six weeks ago," Cathy said. "Finally I have a lover who understands me and enjoys the things I do."

I watched Michaela as she also listened and moved to sit tightly along side Cathy. I was attracted to her in the same manner as I had fallen for Florence. The change of my dressing had allowed me to realize how deeply I loved being near women.

Celone smiled at me as she spoke, "Florence met Jamey about the a month ago too. Jamey hasn't left her side since. She is like a sister to us now."

I considered the four other women near me. Michaela and I were about the same height and shorter than the others.

Florence stood, "I came to dance. Please come with me Jamey."

I had been practicing with her and she had been a good instructor but I nearly tripped as I stood.

"That was close," Celone said as she reached to hold my arm. "Enjoy Jamey but careful now."

"Let's all dance," said Cathy and the others also moved to the floor.

We danced for the entire set and my feet needed a break. Michaela took my arm as she wanted to rest as well.

She spoke softly, almost whisper quiet but I heard her clearly as we stepped to the table.

"You move quite well for a boy Jamey. I only noticed when you started that hip thing you just did next to Florence. That's a rocker move from Mick."

She squeezed my arm slightly as we reached the table. I was anxious as we stood looking out at the others as they enjoyed the beat.

"I can imagine how difficult it is, I meaning learning so many things quickly. It was a subtle thing I noticed so do not be concerned. I will not say anything."

I was immediately next to her as she turned to look at me and then I saw the small bump on her neck just beneath the pearl choker.

"You are a boy too?" I asked.

We sat and quietly discussed how we both had come to be with these beauties. The three girls were unaware and had matched up with others on the dance floor. Seeing Florence and Celone move on their tall heels impressed me and I asked Michaela about her girlfriend Cathy.

"Cathy is wonderful but I have only been with a few women you know. She can be aggressive towards other girls but she has been great for me. I needed someone who can make me happy and handle stuff I can't. I guess I would say I'm a bit passive like that but she is kind."

I felt comfortable with Michaela but wondered if anyone else had read me tonight.

She saw my concern, "Jamey, you are doing wonderful for having been a girl less than a month. Florence is clearly into you. Even now she is smiled as she looks at you."

I saw that she was dancing with a tall guy now but I wasn't jealous. The ponytail the man wore reminded me of my recent past.

I told Michaela of my singing with the band, "but I've not found enough of a feminine voice to try to sing."

"You know there are coaches that can help. I can sense and feel that Celone is the primary of her sister and you. You just need to ask her for a coach and she will find someone Jamey. As meek women we need to have that guidance correct?"

I saw the three women coming back.

"Can you text me so that we can share Michaela?"

Cathy looked at me and I knew she sensed what we had been talking about. It could have been a subtle look from Michaela as well but she just smiled.

"I am happy the sisters have found you Jamey," Cathy said.

Later after more dancing Michaela walked toward another table to talk with a tall girl and I accompanied her. She introduced us.

"Tony and I work together and are close friends."

I felt Cathy at my side as she moved to Tony and they kissed lightly.

Tony said, "I haven't seen you here before, Jamey right?"