Watching Jenna

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.