Brett's Transformation to Brenda

This is a true story about my first real long-term relationship. My name is Brett. I am now 30, but this story begins at my young age of 21.

I was single and living a quiet life. My life consisted of sleep, work, and lonely nights on the internet. I had only 1 close friend and he was away in the military. I was still living with my parents and could never find a special woman so I was quite active in pornography.

One day my life changed when I was exploring a chat room to talk with single women in my area. I was pretty quiet in the chat room when I received a private message from a person with the screen name RedAmber81.

She wrote, "hi."

I replied, "hey."

She wrote, "I'm Amber, 24 swf."

"My name is Brett. 21 swm."

We continued talking for hours. We began talking about our likes and dislikes. I thought I was smooth and began talking about sex like most men would. I was quite surprised that she was so open.

Amber was talking all about her past relationships and how they ended. I told her the same even some embarrassing moments about how I prematurely ejaculated. I figured since this was just a chat it wouldn't go far, but I was wrong. Amber was interesting and kinky.

She was telling me about her kinky past. She was saying how she liked black men, small and large penises. She was so open that she said she liked guys who were open to wearing panties for her.

As I'm reading all the things she is telling me I can't help but notice how erect I'm getting. I was getting turned on by panties and her wild side.

I have never worn panties before, but the idea was intriguing. I didn't think I would ever meet her in person so I was willing to tell her about my flaws.

I said, "Well I'm a unique kind of guy."

"How so?" She asked.

"I have an unusual small penis for a grown man." I replied.

"Oh. Well I'm sure you are bigger than you think. Do you mind if I ask how big you are Brett?" She asked.

I pondered how to reply. I never thought she would ask.

"My penis is 4.25" long." I said.

There was a pause from her next response. I figured she was laughing and left, but I was wrong.

"That's not as bad as you think. Could I see a picture of it?" She asked.

"Limp or erect?" I asked.

"Both!" She replied.

I stood up and removed my shorts looking at my limp penis. I took my phone and shot the first picture. I began playing with my penis and it started to grow when I heard a ring on the computer. I looked up and saw a picture of Amber. She was topless!

"Maybe this will help you get hard for me!" She said with a smiley face.

When I saw her full beautiful white breasts I about had an orgasm. I was stunned that she was so open. I took a picture of my now erect penis and sent both to her.

"I think your penis is cute. It is smaller, but I like it. Don't be ashamed of your penis because it isn't 8 inches" she wrote.

"Thank you Ms. Amber. Unfortunately it is hard to like when my penis falls out of my boxers because its so small. I haven't been able to find underwear that fits my small penis properly." I said.

"Have you thought of other alternatives sweetie?" She asked.

"What do you mean?" I asked.

"Panties!" She said.

My heart began racing as I had thought about it before. The tight panty material holding my little penis in place gives me shivers down my spine. I didn't want to seem like a pervert to her, but she brought it up.

"No I haven't." I said.

"I find it arousing when a guy wears panties." She wrote.

We talked all day and night. I was getting to know her so well and was beginning to like her so much. She didn't mind me having a small penis and was kinky.

Amber and I stayed in contact via internet for a few days before we talked on the phone. Our conversations turned sexual after a week and we were regularly having phone sex with one another. After a couple of weeks, I finally had the courage to ask her out. And much to my surprise, she accepted.

Our first few dates were pretty vanilla. We went to dinner, movies, and dessert. Our 8th date was when I was falling for her. She had me wrapped around her finger and I was doing all I could to please her.

We were out to lunch one day when she said she wanted to see me in panties. She told me it was one of her biggest fantasies and turn ons. I finally caved and said I would wear them for her. Like I said I was willing to do anything for her, but I didn't have the courage to buy them.

She said, "Well let me help you. After lunch we will go together to Victoria's Secret and I'll buy them for you." She said.

My heart and head were pounding. Could I really do this I thought to myself. I have always worn boxer and even though my penis doesn't fit correctly, it was the natural thing to do. But I liked her, maybe loved her. I felt my penis twitch as she smiled at me knowing I was going to be wearing panties for her.

She hugged me and kissed me on the cheek. She held me close to her and asked me if I was ready. I was, but was nervous. As she held me my penis began to stir. I felt my face get red and I knew she could feel it.

She smiled and said, "looks like your lil guy is ready to be pantied!"

I blushed as she kissed my forehead. I just held her and couldn't let go. My mind was a haze, but my penis was controlling me. I was under her control like she was a mistress and I was her slave. I couldn't do anything unless she wanted me too. I was helpless, yet satisfied.

As we sat in the mall food court next to one another she held one arm around my back. She reached her right hand around to the front of my jeans and rubbed my penis. I was so horny I laid my head on her shoulder as she slowly rubbed my penis through my jeans. She kissed my ear.

"I love your lil penis Brett. I can't wait to see it in some sexy panties!" She said.

She released my penis and kissed my cheek again. She grabbed my hand as we began walking through the mall. My face felt flushed and my penis was hard as a rock. I was walking hand in hand with this beauty queen. I stuck my cheat out knowing guys would stare at the girl at my side wishing they were in my position.

We made our way to Victoria's Secret. She pulled me inside and we began looking at panties. She lifted several up in the air and showed them to me. She quietly asked which ones I liked. I felt my penis begin to stir in my jeans. My heart beating feeling like my chest is going to explode. I point at a pair of bikini style cotton panties with "hot stuff" on the butt. They are white with hot pink lettering.

Amber smiles and we begin walking around. We looked at so many pairs of panties. I picked out 4 other pairs. As we arrive at the register I begin to shake nervously wondering if the young female employee knows that the panties are for me. My thought are unraveling and my heart is beating fast. I feel like I'm having a panic attack as Amber tells the girl she loves her new panties.

After Amber paid, we walked out together holding hands as we walked to her car. She smiled and told me to get in. As I sat in the passenger seat she asked, "which pair do you want to wear?"

"I don't know Ms. Amber." I replied.

She picked up the yellow full lace bikini style and handed them to me. I took them and began to undress in her car. As I took my boxers off she sat there starring at my penis which was standing at attention. I placed my boxers on the center console and began pulling the panties up my legs. She grabbed my boxers and took them while I finished with my panties. I grabbed my pants to pull them up, but she stopped me.

She reached over and rubbed my penis through the lace panties with her fingernails. The feeling of her nails rubbing lightly on my penis through the material had my on edge. She leaned over and kissed me telling me how hot I looked in panties.

"Get your car and follow me sweetie." She said as she started her car.

I pulled my jeans up and got in my car and followed her to her house.

When we arrived I walked up to her house behind her holding her hand. We walked inside and she turned around and began kissing me. She had her hands around my neck as I placed my hands on her perfectly shaped butt. My hands were a little shaky as it had been almost 3 years since I last had sex. She stopped kissing and giggled at me while unbuttoning my jeans.

She pushed me back lightly until I sat on the couch. She lowered herself to her knees and removed my jeans while kissing my thighs. Butterfly feeling was in my stomach as she continued kissing my thighs slowly moving to my panty covered penis.

Kissing my penis through the lace panties made me moan and squirm. I was at her whim as she controlled every moment with each kiss. She began licking my penis causing it to twitch ever so lightly. I felt myself on the verge of cumming as I touched her shoulders.

"Awe is your little guy going to cum for momma?" She teased as she continued licking my penis.

"Y.. Y.. Yesss." I moaned.

"Call me Ma'am. It turns me on when you are submissive to me!" She said.

"Yes Ma'am." I said.

"You better not make a mess in your panties. Its not proper for a little girl to make a mess in her panties. Do you understand?" She said.

"Yes Ma'am." I said breathing hard and fast feeling the cum moving from my balls to my shaft.

She pulls my panties down and my penis springs up finally let go from the my lace covered confinement. She kissed the head of my penis causing me to squirm. Feeling every tingle in my body as her soft lips touch my sensitive penis. She stands and walks to her bedroom returning with condoms in her hand. She pulls out the magnum condom and rips the package open. She places it over the head of my penis and slowly roles it down. Its size is too big as it is so loose on my penis.

"I guessed you would need a different size. Here, I bought this in case your little pee pee needed it." She said as she pulls out a small pecker condom.

She opens it up and places it on my penis. She rolls it down as it fits tight, but not too uncomfortable. She stands up and hovers over my penis. She faces me as she slowly lowers herself onto my penis. I feel the warmth of her vagina as she engulfs my penis in one fluid motion. She looks me in the eye as she lifts her hips up off my penis again. Feeling sad that I'm not longer in her sweet warm vagina, she lowers herself again and moans.

I close my eyes as she picks up the pace. She began riding my penis vigorously and I feel my sperm moving through my penile canal. By her 8th pump, I moan, "ughhhhh... Ohhh..." As I grab her hips and shake uncontrollably.

I try and catch my breath as I'm holding her tight not wanting to let go. My penis shriveling up as it falls from her vagina. I look up at her as she is smiling at me. Feeling like a hero I ask, "How was it Ma'am?"

"It felt different, but good. I loved the tickling feeling my pussy received. Now that you fucked me, its my turn to fuck you." She said.

She grabbed my hand and took my to the bedroom. She laid me down on the bed with my butt facing up. She tied my hands to each corner post and did the same with my feet. She placed a blindfold on me so I couldn't see what she was doing. I could hear buckling noises, but wasn't sure what it was. She steps up close and begins to play with my shriveled penis.

"Just remember that I love you. This won't hurt. You will actually enjoy it Brenda.". She said as she places something at the entrance of my butt.

I feel wet cold lubricant and a circular hard object against my anus. I begin to worry as she slowly slides it in. It only took me a minute to realize that she was literally fucking me. I lie still as she continues pushing her dildo into me. She begins kissing my back and neck as she brings her pace up. The tight feeling in my anus is causing pressure. It is an uncomfortable feeling yet my penis was growing. She starts to speed up her pace causing me to scream in pain and pleasure. Continuing her assault on my anus she is now at full pace and ramming my rear. Causing her bed to shake I scream as I feel another orgasm building.

Grabbing the corner posts I'm whimpering as I feel myself shooting more sperm into my condom. Withering in pleasure as she starts slowing her pace. She takes one more deep push and holds her dildo deep in my rear. She falls against my chest and says, "your now my Brenda. Did you like getting fucked by Ms. Amber Brenda?"

"Yes Ma'am," I say as she holds me tight. She removes her dildo and leaves me tied to her bed. She kisses me on the lips and tells me she loves me.

To be continued.