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Brett’s Transformation To Brenda – By tinycuck84 (edited)

My name is Brett. I am now 30, but this story begins when I was 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 unusually 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″ long when hard,” 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 small, but I like it. Don’t be ashamed of your penis because it isn’t eight inches,” she wrote.

“Thank you, Ms. Amber. Unfortunately, it is hard to like. I haven’t been able to find underwear that fits me 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.”

My heart and head were pounding. Could I really do this, I thought to myself. I have always worn boxers and even though they’re really baggy in the front, 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 little guy is ready.”

I blushed as she kissed my forehead. I just held her and couldn’t let go. My mind was a haze, but my penis were 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 to. 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 little 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 chest 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 unravelling 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 staring at my penis which was standing at attention. I placed my boxers on the centre 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 me 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. “Aww… Is your little guy going to cum for mama?” She teased as she continued licking my penis.

“Y-Y-yes,” 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. It’s not proper for a little girl to make a mess in her panties. Do you understand?”

“Yes, Ma’am,” I said, breathing hard and feeling cum moving from my balls to my shaft.

She pulls my panties down and my penis springs up finally let go from the 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 shrivelling 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, it’s my turn to fuck you,” she said.

She grabbed my hand and took me 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 shrivelled 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, “You’re 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.

*****

I opened my eyes slowly and yawn after a long sleep. I tried to move my feet to get up, but they are still tied to the bed posts. I tried moving my arms and I noticed they are tied to the headboard posts. My eyes widen as I feel my naked body underneath the bed sheets remembering the night before. I tried to wiggle loose, but there is no use as I am completely secured to the bed. I can feel a light pain in my ass. It doesn’t sting, but tender as I recall my orgasmic night with Amber.

My heart beats faster knowing I allowed her to not only buy me panties, but use her dildo on me. I’m not gay by any means, but I felt so sexy and loved being held by Amber as she made love to me.

“Good morning sleepy head!” Amber said as she opened her bedroom door.

“Good morning babe!” I respond.

“I thought we established that you are to refer to me as Ms. Amber last night sweetie! Was there anything unclear about that Brenda?” She asks.

I couldn’t believe it. I thought it was all her kinky side while we had sex. Does she really want me to call her that all the time? I open my mouth to respond, but think better of it. I mean I’m naked on her bed and tied down.

“You were very clear Ms. Amber” I said.

I watched as she was standing in front of me wearing just her robe. I could see the bumps of her nipples through her tight thin satin robe. I kept thinking to myself how lucky I was. I’m in a gorgeous woman’s bed, naked, tied up, and just had the most amazing sex of my life.

Amber walked seductively the bed. She grabbed my cock through the sheets and leaned her head on my chest. Slowly stroking my tiny penis causing me to twitch knowing I couldn’t deny her. She looked up at my face smiling at me. She had the look of conquest as she knew I was her property. Even if I wanted to leave she knew I wouldn’t.

She stopped touching my cock as she leaned in and kissed me. I felt her warm lips caress mine. Her wet warm tongue dove into my mouth as she continued kissing me even further showing her dominance over me. She broke off the kiss as she caressed my chest.

“Did you enjoy yourself last night Brenda?” She asked.

“Ye… Yes Ms. Amber.” I moaned.

“Does your little pee-pee want to feel my hot, wet, tight pussy?” She asked.

“Ughh! Yes Ms. Amber. I will do anything to feel your pussy!” I said.

She sinfully smiles at me. She pulled the sheets away from my trembling penis. She took my penis in her small sexy hands which engulfed it. I couldn’t see any part of my penis as she began stroking it slowly causing every nerve in my body to twitch.

“You must beg me to fuck you. I want to hear you say, please Ms. Amber, fuck Brenda’s ass with your dildo. I want to feel your dildo in my ass and know what it is like to be fucked like a girl!” She said.

Without thinking of any consequences I repeated what she wanted. I begged like a slut to be fucked in my ass. I had no idea what was going to happen or if I would ever be released. I pondered how I got into this kinky situation.

Amber continued to massage my penis. Pinching my nipple with one hand and slowing massaging my penis inching me closer to orgasm. I closed my eyes feeling pleasure from the tips of my toes to my head. I had the butterfly orgasmic feeling in my stomach as Amber bent down and kissed my forehead.

She released my nipple and penis. She walked over to her night stand and removed a butt plug. On the end of the butt plug was a pink medallion with the word “sissy” engraved in it. She walked over and lifted the butt plug next to my mouth.

“Moisturize it for you butt baby.” She said.

I opened my mouth and she lowered it into my mouth. I began sucking on the plug slowly wanting to ensure it would slide daily in my butt. Amber took my penis and engulfed it in her warm saliva filled mouth. She cupped my tiny balls as she sucked my tiny penis slowly milking it.

I sucked harder feeling my sperm start to boil in my balls. Amber continued on my penis and squeezed my balls harder which tipped me over the limit. My hips bucked as I shot load after load into Amber’s luscious hot mouth.

“Ugh!” I moaned, feeling the most pleasure in the two days with Amber than ever before in my pathetic sex life.

My hips started to relax as my orgasm subsided. My breathing slowed. My penis slowly shrunk inside Amber’s mouth.

Amber released my penis from her mouth as she turned to my face. Her devilish eyes and sexy smile made me feel more love and passion than I could have ever dreamed. She bent down and placed her lips on mine. She kissed me with passion and love. I opened my mouth and accepted her kiss. I felt her tongue on mine and the hot salty liquid moved onto my tongue slowly sliding towards the back of my mouth. She held her mouth to mine as I knew she was forcing my sperm into my mouth. It had a salty taste. My own sperm being transferred from Amber’s mouth to mine. I knew what she wanted me to do so I swallowed my own sperm.

Amber released her mouth from mine after I swallowed all of my sperm. She smiled at me and said, “I’m so proud of you Brenda!”

She took the butt plug and moved towards my butt. She spread my cheeks apart as she placed it at the entrance of my anus. She pushed slow and moderately, inch by inch until it was buried deep inside. She held it in place as it filled me completely. She slowly retracted it from my anus and pushed and pushed it back in. I started to moan as it didn’t hurt. It gave me pleasure as she started fucking me with her butt plug causing my penis to rise again.

She continued fucking me as I noticed her other hand reached for her night stand. She pulled out a cream and placed it on the bed. My eyes were full of haze from the pleasure and couldn’t read what the cream was. She lifted the cream to my penis and squeezed causing a think white cream to land on my penis. She began rubbing the cream all over my penis. I wasn’t sure what it was at first, but I soon discovered it was a numbing cream. She stopped toying with the butt plug and left it deep in my now sissy butt. She took a condom and rubber band from her night stand and slowly placed it over my penis. She took the rubber band and wrapped it tight at the base of my penis to ensure the big loose condom would stay on my little penis.

She stepped on the bed and wrapped her legs around my waist. She grabbed my penis and aimed it at the entrance of her silky wet shaved pussy. I watched as she lowered herself on my penis barely feeling anything from the cream and condom.

Amber slowly began riding my penis. She held onto my thighs as she moved up and down. I watched in displeasure knowing I couldn’t feel a thing wishing I could touch her. Her pace picked up as she vigorously began riding me. The bed was squeaking and shaking as she began to moan. She used her hand and rubbed her clit. Her big beautiful milky breasts were bouncing in every direction. Her eyes closed and looked to be having fun and filled with pleasure. She remained on my penis and rubbed her clit as her breathing increased. Her moans were louder as she approached an orgasm. I felt her legs tense around me and squeeze as she let out one last scream. Her upper body fell lifelessly on my chest as she just enjoyed an orgasm.

I felt like a stallion knowing my penis was part of the cause which made her orgasm.

“Ms. Amber, thank you for allowing me to be in your pussy!” I said.

She didn’t respond. I looked at her and could feel her breathes were long and deep. She orgasmed so hard she fell asleep. I smiled and kissed her head as I closed my eyes and fell asleep with a beautiful naked woman lying on top of me.

I woke up later that day and found Amber next to me still naked. She was staring at me. I felt my arms were in a different position and noticed she had removed the bonds. I rolled over towards her and kissed her beautiful pink lips.

She smiled at me and said, “I have to go visit a friend. Would you like to come?”

“Yes Ms. Amber.” I said.

She stood up from the bed and told me to get dressed. I stood up and walked with her to her closet. I grabbed a pair of my panties from the bag and began sliding them up my legs. I pulled them up and could feel the electricity they gave me knowing how cute she thought I would look. Once in place I saw my little penis stretch the front of the panties a bit. Amber walked up to me and said I needed to readjust. She took my penis in her hand and slid it under between my legs and pulled my panties back up. I looked and saw how feminine it made me look, but I couldn’t help but leave it as I saw the twinkle in Amber’s eyes.

After getting dressed we got in her car and drove to her friend Trish’s house. While in the car she was explaining to me about the relationship between Trish and her husband. She had said Trish cheats with her boyfriend even though her husband is clueless. She had said that is how she became interested in cuckolding.

When we arrived, I finally met Trish. She was just as beautiful as Amber, but had dirty blonde hair and blue eyes. Their bodies were similar with the exception she had much smaller breasts than Amber.

As we walked upstairs to Trish’s room, I couldn’t help but stare at her cute little butt. It was wiggling in my face and caused my penis to stir. I felt movement between my legs which caused discomfort with the way my penis was positioned. When we entered her room, she looked at Amber and said, “ok, I just have to see it now!”

Amber smiled and turned to me and said, “Drop your pants baby.”

My heart began beating fast. I was so scared because I wasn’t sure what she had told her. Did she know of my panties or my penis? What if she knew both I thought to myself.

I said, “Um, babe. You know that…”

She interrupted me and said, “She knows about us. She is my best friend and I tell her everything. Baby my family knows you wear panties. Now show her!” She demanded.

My hands began to tremble as I slowly unbuttoned my pants. I pulled my zipper down and slowly started pulling my jeans down revealing my white cotton bikini style panties with black lace. I could feel my penis begin to stiffen between my legs.

I saw Tracy smile and start giggling out loud. I could feel the heat in my cheeks and knew I was blushing as I stood with my jeans at my ankles. Here I was standing in front of these sexy beautiful girls with a tiny penis hidden in panties. Tracy grabbed the front of my panties and felt nothing there. She took her forger tips and lightly scratched the panties directly over my penis causing my legs to tremble.

“I would like to see the little guy.” Tracy said.

I couldn’t deny Tracy’s request after looking at Amber and seeing her facial expression. My heart was throbbing and my mind was racing. My thumbs clasped the lace waistband and I slowly started pulling the panties down. I felt my hands shaking as I look towards Tracy. I continued pushing the panties down watching as Tracy’s hand went to her mouth. He eyes widened as she began giggling as my penis dropped between my legs.

I let go of the panties as they dropped to the floor. I kept my hands still even though I wanted to cover myself. Tracy moved closer to me to examine what she was seeing. I looked down as she was now inches from my penis. I could feel her hot breath hitting my groin which caused me to become aroused. I felt my penis beginning to rise and become erect as this beautiful woman was close enough to lick me.

Tracy’s eyes looked up at me as she gave me a devilish smile. She opened her mouth slightly and began blowing her breath on me. I was doing everything possible to ignore her, but it was impossible. I closed my eyes as I was losing control. She blew harder and my legs twitched as I felt myself losing this battle. I couldn’t hold off much longer. I moaned as I began cumming. I lost control again and my penis continued to spurt after spurt until I had nothing left.

Breathing deeply as my orgasm slowed to a stop I opened my eyes and could hear Amber and Tracy laughing hysterically. I was ashamed and embarrassed that I came without even being touched. I felt so pathetic, yet so relieved from my orgasm.

“I can’t believe he came! Oh my god, that is the funniest thing I have ever seen.” Tracy said.

Amber giggling as she said, “I love that he is such a premature ejaculator. It’s cute.”

“Well he is premature, that’s for sure!” Tracy said.

“Well Tracy, I promised you would see him. We are gonna leave. We are going to his parents’ house for dinner.” Amber said.

I bent down to pick up my panties and jeans. I stood next to Amber clinging to her arm. We walked downstairs as Amber and Tracy hugged and said their goodbyes.

“It was nice to meet you Brenda,” Tracy said.

“You too,” I replied as Amber and I left.

The End.