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A Night At The Movies. Part 4

His first time experience continues.

I don't know what time it was when finally fell asleep on Friday night. All I know that my deep slumber was interrupted by the buzzing of my alarm clock. Why did I set my alarm so early on my day off? It was only slamming my hand down to silence the buzzing that I remembered that Fern had invited me over.

As I commenced to get ready the old fears and questions began to creep back into my mind. What about my job at the radio station? I had busted my ass and called in markers to get that gig. What if I'm seen and it's reported to the station?

"If you had kept your lust and curiosity in check, you wouldn't be in this situation," I told myself.

Just then my cell phone buzzed and jolted me back to the now. It was Fern on the other end.

"Good Morning," she greeted me.

"And to you. I was just getting ready to come over," I informed her.

"I was making sure you had not forgotten," she replied.

"No way," I responded.

Once again, I cursed myself for being weak as drove to her apartment. Soon I found myself at her door and was once again admitted into her apartment. I was blown away at the sight before me. Fern was wearing a French maid outfit and she looked better than any fetish model.

I was greeted with a long kiss before she took me by the hand and led me to her bedroom. There on the bed was a black satin robe and a pair of black silk bikini panties.

"Would you wear these for me?" she asked.

"Why?" I asked feeling a little uneasy.

Fern must have sensed my hesitation and gave me a reassuring smile.

"You like the feel on my lingerie against your skin? It's even better when both parties are clad in silky garments," she continued.

I removed my clothing and donned the outfit left for me and I had to admit they felt wonderful against my body. The feel of my cock and balls cradled in the tiny silk undies and the satin robe had me hard as soon as I put them on. I then headed to her living room and took a seat on the couch.

Fern appeared with a silver tray laden down with a coffee pot, cups, saucers, spoons, and milk and sugar containers. I stared at her beautiful legs that were clad in seamed nylons as she poured. When she bent over to retrieve a dropped napkin, I was able to see the white ruffled panties she wore underneath her short maid's skirt and the ribbons that held up her nylons.

She took a seat next to me and raised her coffee cup to indicate a toast. I raised my cup and we touched them.

"To a good morning," she said before we took a sip.

She set her cup down and ran her finger over my thigh that was hidden by the robe.

"Feels good, doesn't it?" she asked.

"Yes, it feels great," I responded as I ran my hand over one of her nylon clad legs.

I finally questioned her about the reason for this early morning meet. She responded that she was leaving town this evening but wanted to spend the day with me.

We shared long tongue kisses as our hands ran over each other silky clad bodies. I was given another great blow job and responded by shooting my load in her sweet mouth. There was a pause while she cleaned up and the next session began. This one would be all for her.

I intercepted her as she headed back toward the bed and removed her maid's uniform and her tiny bra. I then laid her back on her bed and commenced to lick and kiss her beautiful breasts as my hand slowly tugged her ruffled panties down. I gently took hold of her small but very hard cock and began to jack her off as we kissed. Her moaning was the sexiest sounds I had ever heard.

Fern announced that she was cumming and I pointed her cock at her belly and she emptied her load there. I was as hard as I could be when I flipped her on her front and prepared to shove my cock in her tight ass. It the blink of an eye, she flipped onto her back again and gave me an apologetic look.

"I'm sorry, but I don't like anal," she said.

Being a gentleman at heart, I didn't press the issue and told Fern that it was okay.

Fern smiled as she reached in the drawer of her nightstand and removed a bottle of lube. She placed a generous portion between her magnificent breasts then mounted me. Fern grabbed my swollen cock and placed it between her tits and then, using her hands, she pressed her tits together sandwiching my cock between them.

Fern then began to side her upper torso up and down stroking my cock between her slippery soft tits. We kissed each other's ears, neck and lips as she rode me. When I announced that I was going to cum, she increased the speed of her stroking and urged me on and I shot my load between her breasts with some of if striking her chin.

And so the day went. Many hours later as night approached she informed me that it was about time for her to get ready to leave. I cleaned up and redressed. I found her sitting on the couch clad in the silky robe that I had worn.

"I will be gone for a month, maybe longer," she stated as I sat down next to her.

"Can you tell me where you are going?" I asked.

"No. We can chat via online every day," Fern continued as she handed me a piece of paper with her email address.

The look on my face caused her to slid closer and embrace me.

"It's not forever and you don't have to remain celibate. I'm sure there are interns at your radio station that want to ball one of the air personalities," she went on.

"There are," I responded.

"Good. Fuck your and their brains out. Just don't forget about me," Fern stated and I received another kiss before she shooed me out the door.

The weeks crawled by and I missed my little t-girl more than I believed possible. I did chat with her every other day and it helped. I did not seek an intern to fill my bed as Fern suggested. I would jack off and think about my time with Fern. It was about three months later that she informed me that she was heading home and my heart leapt with joy and anticipation,

I was asked to be at her apartment on Friday night around eight. The key would be hidden under the welcome mat and I was to let myself in and announce my arrival. Finally, Friday arrived and I flew to Fern's apartment and admitted myself. There were a dozen lit tea candles decorating the room and burning sticks of incense.

I called out to her and she answered from the bedroom. I pushed open the closed door and could not believe the sight before my eyes. There sitting on her bed was for Fren in a bridal nightie. A long veil fell from the top of her head to down to her mid-thigh. The edge of the veil met the tops of her white thigh high nylons.

As I drew closer, I could see the white silk and lace garter belt that held up her stockings and the tiny panties. As I stood before her, she gently parted her legs to reveal small bulging crotch. She rose to her knees and embraced me and I received a long-awaited kiss and embrace.

I ran my hand over her veil covered shoulders and arms and down to her legs. One their way back up, I allowed my fingers to brush across the tiny white silk triangle between her legs and she shivered with delight.

"Are you surprised?" she asked as she released me with her face mere inches from mine.

"Very," was all I could say.

"This is a honeymoon as I am going to give you my cherry," she whispered.

"I have questions," I stated.

"I went to Thailand for sex reassignment surgery but chickened out. So I spent two months investigating the sex trade and talking with the other t-girls there and learning all I could about anal sex," she responded.

I slowly removed my clothing until I was down to my boxers. Fern then laid back on the bed and requested that I remove her panties. 

I knelt on the bed with my knees on the outside of her legs and began to slowly slide the tiny garment down. Once it was removed, I discovered that there was a perfect looking pussy underneath. My cock hardened as she tugged my boxers down and then opened a bottle of K-Y and covered my shaft.

"Don't you want me to wear a condom?" I asked.

"No. I have never allowed another man there. You will be my first and I want to bareback," Fern stated and she flipped over onto her hand and knees and raised her ass in the air.

I moved in closer and pushed her veil to one side as I placed the head of my cock at the entrance to her butt.

"Be gentle. Remember, I'm a virgin," she said in the sexiest and softest voice I ever heard her issue.

I gently pushed my cock a little way inside her and she moaned with pleasure.

"More," she begged.

I pushed myself in a little deeper and she moaned a little louder and begged me to go deeper. Soon, I was totally inserted and my balls were banging against her. I placed both my hands on her hips and began a long slow pumping movement. My months of abstinence had lowered my resistance and it wasn't before I was ready to shoot my load.

"Fill up my ass," Fern begged over and over.

Less than a second later I held her tight against me and emptied myself into her. I slowly withdrew and Fern laid on her side. Her own small cock was still hard so I took it in my hand. I planted kisses on her lips, neck and breasts and I jacked her off. She finally issued a sexy moan as her body stiffened and she shot her load on my thigh.

We fell asleep in each other's arms. My t-girl was back with me and I could not have been happier I said to myself as I drifted off.

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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