u/Emdaisy9

As we left Stephanie’s place Amber turned and looked at me.

“Have you had a good day so far, Emmy?”

“Emmy?”

“I thought it would be a fitting nickname. And I like it,” she said.

“I’ve been out of my comfort zone a lot today, but everyone has been treating me way better than I could have ever imagined.”

“Well it’s not over yet! We still have dinner plans.”

Amber hadn’t mentioned anything about dinner plans before.

“We’re gonna go home and get changed into something more dinner appropriate first!”

We drove to the house. The entire time Amber drove with her hand on my thigh. She had been doing everything she could to make me feel as feminine as possible, and I was loving every second of it. I would have never imagined life could turn out like this.

We pulled up to the house. Amber slid her hand up my skirt and gave my balls a playful squeeze. She leaned over and kissed me, forcing her tongue into my mouth. We sat in the car for a minute making out before she broke the kiss and looked me in the eyes.

“I love you. Should we take this inside?”

I nodded. We walked to the house, the sound of our heels clicking against the pavement filled the air. Amber was unable to keep her hands off my ass, squeezing it every couple seconds. We got to the door and I reached into my purse to grab the key, as I pulled my hand out with them Amber grabbed me. She spun me to face her and pushed me against the door, interlocking her lips with mine. She grabbed the key from my hand, unlocking the door without breaking the kiss. She stopped pushing me against the door and opened it. I stepped back inside pulling her with me. She pushed me against the wall inside and closed the door behind her.

Amber dropped to her knees in front of me, lifted up the hem of my skirt and she slid under it. She started licking my balls and cage, taking them in her mouth. She put my cage in her mouth and used her tongue to get inside the opening to tease what she could of my clit. She continued to lick and tease. Moaning in pleasure, I felt the plug turn on. My pleasure amplified. I lifted the skirt of my dress so I could look down and see Amber. She looked up at me and smiled with her lips still against me. I pulled her to her feet and pushed her against the wall switching positions, as I got down on my knees. Crawling under her skirt, I pulled her panties down. I started licking at her pussy, paying extra attention to her clit. I could hear her moans. She started grinding against my face, her weight shifted. Lifting a leg. she hooked her knee over my shoulder, pulling my face tight against her dripping hole. She grabbed my head through her dress and held it still as she gyrated her hip and rubbed her pussy on my tongue. Her orgasm was building, she needed and wanted it. Her moans filled the house.

“Lick my pussy like a good girl,” Amber yelled as she continued to use my face. “Fuck right there. I’m gonna cum.”

Her knee gave out as her legs shook violently. Her pussy against my face and her back against the wall were the only things holding her up. The plug was still vibrating in my ass. Her yells and cum all over my face were enough to send me over the edge. I came in my panties and all over the floor. Amber just laughed at me, still in a daze from her orgasm.

“We really are going to need to do something about this. You can’t just keep cumming where ever you want.”

I looked at her, embarrassed. She picked me up off the floor and lead me to the bedroom. She unzipped my dress and in return I unzipped hers.

“I think we should get in the shower to freshen up,” she said.

She lead me to the shower, we hopped in and had a ‘quick’ body wash. It was still a lengthy process. We got out of the shower and dried off. We fixed our makeup and went back to the bedroom.

“I’m going to give you a chance to pick out your own outfit for dinner. Make it good! And for the love of god show off some toe! I didn’t pay to get them done for you to hide them,” Amber said. She slapped my ass and kissed me on the cheek. She already had her outfit picked out and went to the spare room to get changed as to not spoil the surprise.

There was so much responsibility. I didn’t know where we were going so I didn’t have a metric to go off. I decided that I would stick with a dress and heel since I couldn’t really go wrong with that. I walked to my new pantie drawer and rummaged through. I picked out a red lacy thong and slid it on. Then I put on the red lacy bra that I picked out at the store to match. I walked over to my closet and look through the dresses. I pulled out a couple options but one stood out to me. It was a black, knee length, drop waist dress that had a bit of a flare to it. And best of all, it had pockets! I walked over to the shoe rack and looked at my heeled options. I decided on a 4 inch, nude, block heel. I walked out of the bedroom and Amber was waiting for me.

She was wearing a little black dress that hugged all of her curves and showed off her amazing tits and ass. She had on a pair of 5 inch, red, strappy, block heels. She looked absolutely stunning. I couldn’t take my eyes off of her. Amber looked at me, glanced up and down, and did a spin motion with her finger. I did a little twirl for her. When I got back around, I met her gaze.

“You did good, girl!” She said. “Not perfect. But good! Less chance of you flashing the entire restaurant in that dress!”

She walked over, giving me a hug and a kiss.

“I’m really loving the new you! I can’t wait for you to gain more confidence in yourself and be more you,” she said in a loving tone.

I blushed so hard, I thought my head was going to explode. She pulled me over to the couch and we sat down.

“I want to have a little talk,” she said in a concerned voice.

“What’s going on?” I replied, a little worried.

“So. When I talked to your boss about this, she said she would give you this week off work to get used to the changes and settle in. I have also made you a couple appointments this week.” She paused for a moment, “now we need to have the serious conversation. Do you enjoy your new girlie life?”

“I love it! I never thought I could feel so amazing in my own skin,” I replied.

“I know I have been telling you it’s permanent. But do you want that?”

“I didn’t at first. But the idea is growing on me!”

“Ok good. Because we are going this week and are getting you started on hormones, and I’ll call Stephanie and tell her to donate all of your old clothes. She just had them at her place until we had this conversation. Think it over tonight, you can give me an answer in the morning.”

I was gobsmacked. I can’t believe that Amber had really taken me shopping, spent so much on new clothes and shoes, and gotten my nails done while not knowing if this would last forever. For her to give me the choice after all of the effort that she put in. I was shocked. And she really was giving me the choice, not just looking for me to tell her what she wanted to hear. The decision was mine. I had never felt as truly saw as I did in this moment. I knew there was a reason I loved this woman.

“Ok, should we go for food?” Amber asked as she stood up and held out her hand.

I reached out and grabbed it. We walked out to the car fingers intertwined. I looked down and saw our matching nails clasping each other. Then I looked and saw our matching toes in our heels, and my dress flowing around me as we walked. This is what I truly wanted in life. We arrived at the car, Amber opened the door for me and I sat in, she closed it behind me. Amber got into the drivers seat and looked at me.

“You gotta get practicing your driving in heels girl. I can’t always drive,” she said with a smile and slapped my thigh.

She drove us to the restaurant, telling me about the appointments she had made me this week. We talked about starting hormones and what we could expect. I had no idea when she had had the time to do all of this research.

We pulled into the parking lot and found a spot. I looked out my window and recognized the car next to us. It was my parents. I looked at Amber.

“Is that my parent’s vehicle? Are they here? Is that who we are eating with? I can’t see them like this! I’m not ready yet,” I word vomitted in a panic.

“Relax, hunny. You did so well with my parent, you can do this!” With that she got out of the car. Yet again Amber had to open my door and drag me out of the car. We walked towards the restaurant towing me behind her. Entering the door, her a step in front of me, she waved at someone and pulled me behind her through the restaurant. We got to the table and I stepped out from behind her. All of the muscles in my body were tenses.

We stood there at a square table, across from me were my parents. To their left sat Amber’s parents. And to their right was Stephanie and my older sister Megan.

It was Megan who got me started on this journey when we were young. Megan was 4 years older than me, and every bit the older sister. I would have been about 3 or 4 when Megan first dressed me up. Putting me in a princess dress and play heels to have tea parties with her. It was a semi regular thing for us over the next couple years. It felt strange at first, like it was something I wasn’t supposed to be doing, but at some point I settled into it. I started looking forward to these days. Often, when she wasn’t there, I would sneak into her room and try on more of her clothes. As we got older and her style started to get more defined and feminine, I started to sneak into her room more, trying on her dresses and tights with a pair of her heels. This continued all the way up until she moved out. After she moved out she had left some articles of clothing behind, I would continue to wear the limited dresses and jeans until I met Amber. We moved in together and shifted into her clothes.

Megan looked up at me in shock. My mom and dad sitting across from me were sitting with their mouths open. My mom’s eyes filled with tears. Nobody said anything. Everyone eyes were locked on me. Finally, my mom spoke up.

“Wow! I never expected you would show up looking like this. But you look fantastic! I always had a it of an idea but never expected you to go through with it!” She stood up and walked over to me. She embraced me in a big hug and gave me a huge kiss on the cheek.

“I always wanted a sister!” Megan let out a squeal as she jumped up and joined the hug.

My dad still sitting staring, looked at the family hug going on and stood up. He walked over and when girls noticed they let go. My dad embraced me in a big hug kissed me on the forehead.

Leaning back wit his hand on my shoulder, he said to me, “I will always love you. You will always be my child. I’m happy that you finally decided who you want to be in life,” and pulled me in for a tight hug. My mom and Megan joined the hug. I started to cry, tears rolling down my face. As the family hug continued I heard another sniffle. I looked over and my mom was also crying. Looking the other way Megan was crying too. We broke off the hug. Megan wiped the tears from my face as I reciprocated the favour to her. She grabbed my hand.

“Let’s go fix our makeup,” she said.

I looked at Amber and she gave me a look of approval as she sat down in the chair closest to her mom as she too was wiping tears from her face. I looked over and saw Stephanie also wiping tears.

“Do you two want to come with us?” I asked, looking at the girls.

Stephanie’s eyes locked with Amber and they both jumped out of their chairs. Megan guided me by the hand to the bathroom with Amber and Stephanie in tow close behind. We entered the bathroom and went straight to the sinks.

“Ok, fill me in. How did this happen? Amber how did you make my little brother look this beautiful as a girl?”

Amber and I proceeded to tell Megan bits and pieces of the story as we all fixed our make up in the mirrors. I told Megan about how she is part of the reason I felt this way and a big part of why I explored it. I told her about how I used to wear her clothes growing up. I confessed it all to her. She turned and looked at me.

“You actually used to enjoy me dressing you up? I thought you hated it. If I had known you loved it and that you wanted to dress up more I would have given you full access to my closet” she said.

Stephanie looked at me, “girl, you look gorgeous tonight! That dress is working on you!”

“She picked it out herself!” Amber announced proudly.

Stephanie was wearing a blue maxi dress with a low scoop neckline that was showing off her cleavage. She had a nude, wedge shoe on with it.

Megan had on a yellow, fit and flare dress with a black, 4 inch pump.

“Wanna swap?” Stephanie said looking at me.

We all giggled and finished fixing ourselves up. We walked back to the table, the sound of our heels filling the restaurant. We got back and sat down. The waitress came by and took all of our orders.

The 2 families sat there, talking, forgetting the major bombshell that we had dropped on them today. Forgetting that just over 48 hours ago I was living a totally different life. Now I’m sitting in front of my parents and sister, in a dress and heels. This is something I would have never dreamed of in a million years; But because of Amber pushing me I was embracing my new life. Embracing my girlie life and loving it!

After we were all done eating. Lenny paid the bill but not without a debate from everyone. Amber, Stephanie and Megan were talking about yesterday’s shopping trip and stealing of all of my male clothes.

“Can I come shopping in your new closet?” Megan asked.

“Only if I can come shopping in yours!” I replied.

“Duh! That’s just what sisters do!” Megan rolled her eyes jokingly.

“Can I come too?” Stephanie interjected.

“Haven’t you taken enough clothes from my closet?” I said and winked at her.

Amber and Megan started laughing. Megan put her hand on mine and leaned over the table.

“Hey Amber!” Megan said, “is it ok if me and my little sis spend some time together this week? Shopping and lunch date?” She asked shifting her head to me.

“Of course! That’s perfectly fine with me!” Amber replied.

I looked at Megan and nodded, “I would love that!”

At that, it was settled. Me and Megan were finally going to hang out as sisters! We were going to do something that I had been wanting to do my entire life. Now it was becoming a reality.

Once everyone was done chit chatting and was ready to call it a night. Everyone stood up to leave. Amber grabbed my hand and we left the restaurant. Once we got outside we all said our good byes and hugged each other.

“I’m proud of you, sweetie,” my mom whispered in my ear during our hug.

“You will always be my kiddo,” my dad said.

“I’m excited to finally have a sister. I’ll text you to make plans,” Megan whispered in my ear.

Amber and I sat in the car. Before she had even turned on the car, the words spilled out of me,

“I want to do it. I want to commit to the transition,” I basically yelled.

Amber squealed with excitement. She leaned over and gave me a huge hug and kiss.

“I’m thrilled. I saw how happy you were tonight and thought you might say that! And remember, this doesn’t change anything between us. You’ve just become my girlfriend now!”

The drive home was spent with Amber telling me all the fun things we could do now as girlfriends and I just sat smiling, enjoying every moment of it.

That’s the end of part 4. Part 5 is on its way!

We finished up getting the last of all the new clothes put away. I still couldn’t believe that Amber had told her sister. Better yet, I couldn’t believe her sister would do that. But I wasn’t super upset about it. I was living in my ultimate fantasy with all the new clothes we had gotten from that day. Amber spared no expense.

Amber gave me a full lecture and lesson on how to sit like a lady after the accident we had at the mall today. After a little bit of time I finally figured it out. As we were getting ready for bed, Amber showed me how to take off my make up efficiently. I changed into a new pair of pyjamas. They were blue satin short shorts with a matching short sleeve button up. While sliding on the shorts one of my nails broke off.

“Oh my. This won’t do.” Amber said looking at the nail on the floor, “tomorrow we are going to get matching mani pedis.”

We proceeded to take the rest of the nails off and climbed into bed.

The next morning I awoke. Amber wasn’t in the bed, which I thought was strange, but didn’t think too much into it. Like the day before, I rolled out of bed and went to shower. I repeated all the steps Amber had given me. I stepped out of the shower and dried my self off. I walked into the bedroom and Amber had laid an outfit on the bed for me. It was a pink high neck tank top style bodysuit with a jean skirt, with a nude push up bra and matching nude thong. With a new pair of pink strappy sandals that matched my shirt.

I put on today’s outfit, then went to the bathroom and did my make up. Since we were going with a pink theme for the day, I did my make up to match. Pink eye shadow and a pink lipstick. When I was happy with the look I applied my wig. Amber was waiting for me on the couch, fancy coffees in hand. As I walked out she looked me up and down inspecting my outfit. She gave me the nod of approval. She was wearing the same outfit, but in white rather than pink. Her hair was in a high ponytail with a white scrunchie.

“I think we’re ready to go!” She said grabbing our purses and handing mine to me.

We walked out to the car, again she opened the car door and watched as I sat down to close it behind me. She got in the drivers seat and we set off. On the drive over I voiced my concerns.

“I don’t know how I feel about having my nails permanently done.”

“Good girls always have their nails done,” she replied firmly.

“What about work? I can’t go to work like this,” I protested.

“Oh, don’t worry, hunny. I’ve already emailed your boss and informed her of the situation.”

“What do you mean ‘situation’?”

“Well you seen, hun. You wanted to dress and act like a girl. So from now on you will be a girl, forever. No matter what!” Her words were so matter-of-fact.

I was still comprehending the situation and the conversation we just had when we arrived at the Chinese nail salon. Amber got out and walked around to my door and opened it. I didn’t move. Amber grabbed my hand and basically dragged me out of the car. We walked into the salon and Amber walked up to the counter. She had a conversation with the lady behind the counter and waved me over. We both walked a row of overly large massage chairs and sat down, putting our feet into basins that started to fill with warm water.

We sat there just the two of us for a while. My feet soaked in the epsom salted water, I sat in my discomfort. Eventually the ladies came over to start our pedicures. They both looked at me, took a little longer to look me up and down than most people do. They said something to one another in cantonese and laughed before getting to work on our feet. Amber reached over to hold my hand, I gave her a squeeze to try to let her know how I felt, she squeezed back.The entire process made me feel uncomfortable but Amber was totally unfazed, chatting at me the entire time. The ladies didn’t speck to us much beyond occasionally asking us to hold our feet specific ways or to switch feet. They scraped and scrubbed, grated and lathered our feet. Metal tools were used to cut at our toes, push back our cuticles and were drug under the nails. Sometimes it tickles and I had to keep myself from squirming or giggling, but most of it hurt. Eventually they drained the tubs, dried and lotioned our feet, and pulled out the polish to paint our toe nails. Amber had already picked out the colour and type of polish.

After they were done with our feet, we were instructed to very carefully stand up and move over to tables with lots of lighting and what looked like dentistry equipment. Getting our finger nails done I couldn’t hold Amber’s hand. She had picked out everything for this too, so all I had to do was sit there. A different lady sat down across from me, she smiled politely. Again, there wasn’t much said during the interaction. She started with an electric dremel, grinding away at my nails. It was a weird sensation, almost feeling like it was burning under my nail. She grabbed what looked like insanely long but thin press on nails. Once she glued them onto my raw nails part way down, she started to ask me a question but Amber leaned over and answered, telling her the length and shape. Nail clippers, the first piece of equipment I recognized, were used to bring them to the right length and roughly the right shape before she filed it smoother and a bit rounder. She bypassed me this time, lifting my hand with the one shaped base to show Amber and ask for approval. Amber nodded and the rest of my fingers were done the same. She pulled out several bottles, only one of which actually had colour. She began paining on different layers of various thicknesses and textures, occasionally putting one of my hands under a UV lamp. One of the substances looked like melted hot glue but it wasn’t hot. The dremel came out again to shape the top of the nail. I was very glad when the lady told me that we were done.

After we carefully put our shoes back on I looked down to see what we had done, thrilled with what I saw. We had had matching pink sets done. We had gotten shellac polish on our toes and acrylic nails on our fingers. Amber had picked out a small almond shaped base for my finger nails, while she got long coffin shaped nails with an intricate lace type design on one finger of each hand. She was happy with how everything turned out and she paid. We got back in the car and started driving to our next location. I was admiring my toes and nails and not really paying attention. When I looked up we were at Ambers parents place.

“BABE! WE CANT GO IN THERE WITH ME LOOKING LIKE THIS!”

“Oh hunny, relax. They already know. I called them while you were in the shower yesterday and told them everything. Who do you think gave us the money for the shopping trip?”

Ambers parents were really well off. Her dad, Lenny, was a doctor and her mom, Georgia, was an orthodontist. I had always gotten along well with Lenny. We were able to bond over sports. Georgia and I had a good relationship. We were able to hold a conversation but weren’t close.

“Come on, hun. They wanna meet the new you!”

Again she had to drag me out of the car. She pulled me into the house. Her parents were already standing there waiting for us. Both of her parents looked me up and down. Her dad gave a little head shake. Her mom’s jaw was hanging open.

“Wow. I didn’t expect… him? her? Them? Emilia? What ever you want to be… to look this good. With you looking this good as a girl, I can’t believe you ever wasted your time being a boy,” Georgia said.

“Do you see why I thought there was a girl in our place? And why she will never be a gross boy again?” Amber replied.

“You did good, girl. I’m proud of how well you did transforming her. What do you think, Lenny?”

“Makes a better girl than he ever made a boy.” Lenny said without emotion. “I think this is a huge improvement.”

“Thank you, Dad! I totally agree,” Amber beamed.

Lenny turned and walked to the couch. He sat down and turned on the tv, SportsCentre automatically came on. Georgia and Amber walked towards the kitchen. I instinctively went to walk towards the couch and join Lenny. Amber shot daggers at me with her eyes.

“Emilia! What are you doing?” She scolded. “Girls don’t watch sports! They help in the kitchen with food and drinks.”

I diverted my course and went to the kitchen. I stood at the island and watched as Amber and Georgia as they moved in sync, making lunch as they had hundreds of times before.

“Emilia dear, go ask Lenny if he would like a drink please,” Georgia asked.

I walked over to the couch.

“Lenny, would you like a drink with lunch?” I asked.

“That’s sir to you, you don’t get to call me Lenny anymore,” he said without looking away from the tv.

“I’m sorry. Sir, would you like a drink?”

“I’ll take a beer.”

I walked over to the fridge and grabbed a beer. I opened it and walked back to the couch to hand it to Lenny. As I bent over to hand him the beer I heard a whistle behind me.

“Looking good, slut,” and I felt a slap on my ass. I turned to see who it was and it was Stephanie. “Amber’s done a good job with you,” she said.

Stephanie was 3 years younger than Amber looked a lot like her, but shorter and bit heavier. She didn’t have nearly as nice of an ass or boobs. Her face was rounder and she had shorter hair, just past the shoulders. She was wearing an outfit very similar to ours. A baby blue tank top with black jean shorts and flip flops.

I could feel my face turning red from the embarrassment and fear the ass slap brought. Stephanie leaned over, hugged Lenny and kissed him on the cheek then walked to the kitchen and repeated the process with Georgia and Amber. Stephanie and Amber whispered to each other for a second. Stephanie grabbed Ambers hand and drug her over, grabbing my hand as well.

“Come on, slut. We need to change for lunch,” Stephanie giggled.

Stephanie lead us to her old bedroom. Laying on the bed were 3 identical dresses with 3 different colour schemes. They were midi dresses with a slight puff sleeve, one was pink with white polka dots, one was white with pink polka dots, and one was blue with white polka dots. Looking at the 3 dresses I knew who’s was who’s based on our outfits today. I walked forward to pick up my dress and change.

“Not so fast, slut,” Stephanie yelled.

I turned around and faced the girls. Amber gave me a malicious smile.

“Strip bitch! Stephanie wants to see how your pathetic clit is locked up for me.”

I looked back at the girls. Both standing staring at me with their arms crossed. That’s when I noticed, around Stephanie’s neck was the key to my cage. Had Amber really given her sister the key? I thought to myself.

“We don’t have all day, slut” Stephanie interjected. I nervously pulled down my skirt and undid the body suit clasps, pulling it over my head. I was standing there in just my bra and panties.

“Panties too,” Amber demanded.

I slid my panties down and stood there with my little nub cage exposed.

“Oh, it’s way cuter than I expect!” Stephanie said. Walking closer to get a better look. “May I?” She said and looked back at Amber.

Amber nodded. Stephanie reached out and grabbed it delicately with her thumb and index finger. She inspected the cage, seeing how it worked. “I’m jelly. I’m gonna have to find a pathetic, little bitch I can lock up too,” she said.

After Stephanie had finished her inspection, Amber walked forward. She gave me a kiss.

“You have been such a good girl! Obeying my every word. Now go to the bed and bend over. I have a surprise you.”

I did as I was told. I bent over the bed, bracing myself on my elbows, ass in the air. I heard Amber digging through her purse. I could hear Stephanie giggling as Amber walked close. I felt a pressure on my pussy. I turned my head and tried to look back to see what was happening.

“Look forward, bitch. I didn’t say you could look at me,” Amber snapped.

I felt the pressure building on my hole, it finally gave way and I began letting in what was being pushed from behind. I could feel myself being stretch more and more, then all of a sudden my hole relaxed. I could feel a butt plug in my ass. Amber slapped my right cheek.

“Now, let’s get dressed!” She said with a joyous tone.

I pulled my panties up and looked back. I saw both Amber and Stephanie standing behind me, also in their bra and panties. Amber walked forward and picked up her dress, the white with pink polka dots. Stephanie grabbed the blue with white polka dots. And, as I had assumed before, I picked up the remaining dress, pink with white polka dots. We slid our dresses on and helped each other zip them up. Amber walked over to the closet and pulled out 3 identical pairs of shoes. They were white, strappy, 4 inch heels. We all sat down on the bed to put the shoes on. I felt the plug get pushed deeper into my ass as I sat. We put our shoes on. Amber helped me to do up the strap since I was still getting used to the nails.

We stood up and adjusted our dresses making sure they were sitting right. We walked back out and Georgia looked at the three of us standing in front of her.

“Wow! You all look perfect!” She said. She made us all stand together so she could take a picture.

We sat at the table and got ready for lunch. I sat in between Amber and Stephanie and we started eating. As I was mid bite I got hit with a wave of pleasure from my pussy. Holding back my moan as best I could by shoving food into my mouth. Realizing at this moment the butt plug had been turned on and was vibrating. As fast as it turned on it turned off again. I looked at Amber and she just shook her head, winking at me. I looked at Stephanie and she looked at down at her lap. I followed her gaze, in her lap I saw a remote. I looked back up and met her gaze. She winked at me and blew a kiss. I must have been beet red. The girls on either side of me giggled. I couldn’t believe this was happening.

This whole situation was crazy. There I was. Sat in front of my girlfriend’s family. In full femme. While her sister had the remote to the butt plug deep inside my pussy.

We continued to eat. Stephanie continued to turn the plug on and would leave it going a little longer each time. I started squirming in my chair. Holding in every moan. I was slowly getting closer to orgasm each time. I reach under the table and grabbed both girls legs in an attempt to warn them it was getting close. When we were done with food. Georgia got up and cleared the plate. Lenny got up and went back to the couch. And us three girls stayed sitting at the table. Stephanie turned on the vibrator. My hands still on both girls thighs squeezing tight.

I leaned over and whispered into Ambers ear, “I’m can’t hold it anymore. I’m going to cum.”

Amber reached onto the table and grabbed a paper towel. And then reached under the table and lifted my skirt. She slid her hand under and placed the napkin against my clit. I exploded into it. Some cum leaked out and got into Ambers fingers. She pulled her hand out from under my skirt and held her finger up to my mouth. I knew what she wanted and I licked them clean. Amber gave me the cum cover paper towel and i walked to the garbage to throw it away. The plug still vibrating in my ass the entire time. Building more pleasure. And then it stopped. As I walked back to the table I saw Amber holding the remote. I sat back in my spot between the girls. Amber reached over and grabbed my hand and held it.

As her mom walked back over to sit across from us, Amber leaned over, kissed me on the cheek and whispered in my ear. “Hey Emilia, I love you, I always have and I always will.” I smiled and turned my head and kissed her. I put my head on her shoulder and we just sat and talked with Georgia and Stephanie for a bit.

After about an hour. It was time for us to leave. Stephanie had been dropped off by a friend, so we were giving her a ride home. The three of us grabbed our other clothes from Stephanies room and walked to the door. We said our good byes, Amber and Stephanie hugging and kissing their parents on the cheek. Georgia walked up to me.

“You think just because you go by Emilia now you don’t get a hug” and give me one. Probably the biggest hug she had ever given me. “I’m so happy to have another girl around here!”

I made eye contact with Lenny. I looked at the floor sheepishly and held out my now feminine hand. Lenny just laughed. “I don’t shake girls hands,” he said. Suddenly I was embraced by a hug. “I’m disappointed to be loosing my sports buddy, but you do make a better girl than you do boy. Plus, I guess girls can talk sports too. If Amber will let you that is,” he chuckled.

We left and got in the car. Stephanie was still giggling at the fact she got to play with the remote for the plug.

“Amber this was so much fun. I’m going to find me a good little girl like you have here,” she said.

Amber just laughed at her. We got to Stephanie’s house and she leaned through the middle of the seat. Kissed Amber on the cheek and thanks her for a good day. Then looked at me and kissed me on the cheek.

“You make a good slut. Keep it up!” And she got out of the car. We watched as she walked into her place and then we drove away.

End of part 3. If you are enjoying this series please let me know and I’ll continue to write it!

If you haven’t read part 1 of how Amber caught me dressed up. You can find it on my profile and is worth read before!

The next morning when I woke up I was still in a daze from the night before. Still unsure if it really happened or if I had dreamed it all. Then I felt something I wasn’t used to; the satin pyjamas on my skin. I rolled over and faced Amber. She was already awake, staring at me. Looking as excited as a kid on Christmas.

“Wake up sleepy head. We’re going shopping!”

I guess I got my answer. It had really happened. Amber jumped up and pulled me out of bed. We basically ran to the bathroom with how excited she was. She turned on the shower and got in.

“Are you just going to stand there or are you going to get in?” She asked me from inside.

I stripped off the pyjamas as fast as I could while still getting used to the press on nails from yesterday. And I got in the shower.

“If you’re going to be a girl you have to learn how to do it right,” she said when I got in the shower. “I’m going to teach you how to shower like a girl. And that is the only way you will do it from now on.”

She proceeded to show me the correct shower steps. Amber explained to me that apparently you need to shampoo twice, which I still don’t quite understand, and showed me the right way to exfoliate your scalp. Then she went on to tell me that there is a wrong way to wash your face. I watched closely, I felt like she would somehow know if I didn’t do it just right. She then went on to show me what conditioning tip to root means, even though my hair wasn’t long enough for that to be applicable (but informed me that it soon would be). We went over the proper way to shave your armpits and legs, but I was still pretty smooth from the day before to get away without doing it again. Body wash is far more of a processes than I had expected, but watching Amber get all sudsy… I could have watched that all day long. Hoping that I hadn’t missed anything too important, I zoned back in to hear about the different phases and stages of rinsing that she goes through. At this point, I did begin to understand why there was always so much hair in the shower.

“Ok now you do it while I go and get dressed,” she said over her shoulder as she stepped out of the shower.

I proceeded to repeat all the steps that Amber had just shown me, making sure not to miss anything. When I was sure I was done I turned the shower off, exited and wrapped a towel around myself. I walked to the bedroom to find Amber already dressed. She had on a black t-shirt that clung to her perfect D cup boobs. And a pair of mom jeans, loose but showed off her ass in an incredible way! She completed the look with a basic pair of low cut white converse.

She turned to me, “there you are. I have put your outfit for the day on the bed.”

I looked at the bed. It was a cute pink sundress with spaghetti straps and flowers on it. Next to the dress was a pair of white strappy sandals.

“You can’t expect me to wear this in public,” I exclaimed.

“Good girls wear dresses and cute shoes,” she replied.

“But you aren’t!” I retorted.

“This isn’t about me hunny.” She snapped back and pointed to the dress. Knowing I had entered a losing battle I walked to the bed and noticed something was missing.

“There’s no underwear here.”

“We’re going to have so much fun sharing all of our clothes, but I don’t like the thought of sharing bra and panties. A girl needs her own. That will be our first stop when we get to the mall. So for now you won’t wear any.”

I tried to put up a fight but she wasn’t having any of it.

“Get dressed now, or I will drag you around as you are.”

I felt d defeated. I picked up the dress and slid it on. It was a lot shorter than I would have liked, the hem ifell around mid thigh. Especially paired with the fact I wasn’t wearing any panties yet. Looking down and seeing my flat chest also didn’t fill me with a lot of joy. Next I slid on the shoes, and did up the strap. Amber helped me pull my wig into place and fussed with it a little to make sure it looked right.

Amber then pulled me back into the bathroom and helped me do my makeup. She watched me while doing her own to make sure that it looked okay and corrected any mistakes I had made. Once we were both glammed up, I walked over to the mirror to admire myself. I saw a pretty girl staring back at me. This time I noticed the small details. The way the dress flared enough at the hips to make it look like I had a smaller waist. The way my white toes matched the shoes and how they popped. How my hands looked more delicate with my nails done.

“Hold on, we aren’t done yet. We need accessories,” Amber yelled from the bedroom.

She came out holding stuff in each hand. First she threw a cropped jean jacket at me. Then purse

“Don’t worry I’ve already moved everything from your gross boy wallet into here! Your phone and keys are also in there,” she said as she pulled even more things from her pockets.

Then she grabbed my hands and popped some rings onto my fingers and then slid a necklace around my neck and did the clasp.

“I think we’re good to go!” She said excitedly.

I took one last look in the mirror and was amazed at what she had done to me. I looked like a girl. A real girl. If I had seen myself on the street or at a bar I would have been in awe! She grabbed my hand and drug me out of the house. We nearly sprinted to the car. For the first time this wasn’t because of my own insecurities and fears being seen, but because of her excitement to be seen in the world with me. We got to the car and she opened the passenger door for me, I got in and she closed it behind me. She walked around got in the drivers seat and we set on our way.

We got to the mall. As I got out of the car a breeze suddenly reminded me that I wasn’t wearing any underwear and I got very nervous. Amber helped settle me down reminding me we were going straight to Victoria’s Secret. We walked across the parking lot hand in hand. I could feel people looking. Do they know I’m a boy? Have I been clocked already?

The nerves were getting to me. And then a girl walked up to us, she must have been late teens early twenties,

“You are the hottest lesbian couple I have ever seen” she said.

They think I’m a girl. No body knows!

“Thank you!” Amber replied without breaking her stride and we entered the mall.

Once we were inside, Amber drug me through crowds of people towards our destination. We made a bee line through the mall until we finally got to the first location. I looked up and saw we were at Icing . Not Victoria’s Secret.

“Babe, this isn’t where you said our first stop was,” I whispered to her.

“Relax, come on.” And with that she yanked me into the store.

Amber walked right up to the girl working the counter. I quickly found out that this store is basically an adult version of Claire’s.

“Hi, this is my boyfriend, I mean girlfriend and she’s looking to get her ears pierced.”

The girl looked me up and down, and we made eye contact and she smiled. “Absolutely, right this way.”

She guided me to the chair and had me sit down on a chair about as tall as a bar stool. I had no idea what to expect. Amber and the store attendant whispered in front of me. The attendant walked up to me and explained what was going to happen. She wanted to do both ears at the same time but Amber insisted that she didn’t to be sure they matched. Drawing dots on my earlobes to find a good place the two of them discussed and shifted things until they were both happy. I braced for the pain as she lined up the guide. It wasn’t as bad as I expected but it was enough to make my eyes water. I don’t know if the second was better or worse having known what I was in for. She held up the mirror once it was all said and done for me to see the 1/4 inch sparkly pink rhinestone studs Amber had picked out for me. While I was getting pierced Amber was shopping for “necessities” as she called them. A bunch of different types of ear rings for down the line. We paid at the counter and left.

As we were walking back into the mall Amber leaned over and whispered in my ear, “remember to cross your legs when you sit. Dresses don’t hide much.”

I froze in place.

“Did I just flash that whole store?”

“You sure did, hunny. But next time remember to keeps your legs closed.”

And she grabbed my hand and pulled me behind her as we made our way to the promised first stop, Victoria’s Secret. We walked inside and right to the largest table of panties. Amber started pulling out all different types and styles and handing them to me. I must have had about 30 pairs of panties in my hands. Amber then walked over to a worker. She was about 5’8 with long blonde hair. Skinny, her boobs and butt proportional to her build. But she had one of the prettiest faces.

“Um, excuse me, this is my now girlfriend. Can you size her up for a bra? I know he….she doesn’t really have anything there, but let’s give her something that will give the effect”

I was dumbfounded. Did she really just say that?etf Again the worker looked me up and down, and smiled at me. She took the pile of panties out of my hand and gave them to Amber who also grabbed my purse. She grabbed a long measuring tape from the hook on a nearby wall. Suddenly her face was very close to mine. She had reached under my arms to wrap the tape around my chest, tapping the insides of my arms near my elbows on the way which made me instinctively pull them away from my body. With the tape around me, she adjusted it so it was straight across the middle of my rib cage. Taking note of the measurement she had there, she shifted the tape up so it went across my nipples. She then let go of the one end, pulling the whole thing back through and returning it to the hook. She looked at me.

“Well you would be a 36 AA, but I would recommend a 36 A or B with push up or super push up. Also, don’t worry you look gorgeous! I don’t think anyone will know.” She winked at me and looked at Amber, “do you want me to take all of that to the counter while you continue shopping?”

Amber handed over all the panties and we went over to a wall of bras. Amber threw 4 bras at me, each a different colour and style. She then told me to pick out 2 that I liked. I picked out a red lacy bra that matched a pair of panties Amber had grabbed for me. The second I picked was pink front clasp with black lace. We then went to the counter and paid for everything. Amber took a pink lacy thong and a nude coloured bra out of the mountain of bags and handed them to me. We walked back over to the girl who had measured my boobs and Amber asked her if I could go in a changing room and put on the bra and panties in my hand. The girl allowed it and we walked to the changing room. I slid on the panties and put the bra on. Readjusting my dress. Looking in the mirror and approving of how my new bra made my chest look not so flat.

Leaving Victoria’s Secret we went into a dress store. As we walked around Amber was grabbing dresses, holding them up to me and handing them to me; I had about 20 dresses in my arms. We headed towards the back to the changing rooms. Amber knew one of the workers, Bethany, they whispered back and forward for a second. She let me into the changing room and Amber followed close behind me. After hanging the dresses up, I turned around and she drove her tongue into my mouth. Having no time to process I just melted into the kiss and reciprocated. We stood in the changing room making out.

Amber broke the kiss. Looked at me and said, “reach in your purse, there’s a surprise for you.”

I turned around and reached into my purse that I had hung up next to the dresses. There at the bottom was the dildo from last night and lube. Turning back to face her, she had pulled her jeans down and was wearing the strap on harness. She took the dildo off me spun me back around and forced me to bend it the hip. She put the dildo in the harness, pulled my dress up and pulled my panties down. I felt her hard cock pushing against my pussy. I looked back over my shoulder and looked at Amber

“Wait, we can’t. Not here. People will hear,” I whispered as loud as I dared.

“Relax, I spoke to Bethany, we have 5 minutes.”

She the proceed to push her hard cock into my ass. I was barely able to hold in my moan. She slowly pushed in all the way to the base and left it there for a second before proceeding to pull it nearly all the way. Continuing this motion 3 times before she picked up the pace. Fucking me harder and fast made me moan and my knees weak. I felt her hips slamming against my ass. I had tried my best to hold in my moans, but they kept escaping my lips. I felt the orgasm building in me. I looked at Amber.

“I’m…. going….. to…… cum….” I managed to say between thrusts. Amber pulled out. Spun me around and wrapped her lips around my clit. Again I exploded in her mouth. 4 huge ropes onto her tongue and into her throat. This time she swallowed, then stood up and kissed me.

She leaned in and whispered in my ear, “I’m not done yet. Get on your knees and eat me out.”

I did as I was told. I dropped to my knees and Amber adjusted the harness so I had access to her glistening pussy. Without hesitation, I dove in and started flicking her clit with her tongue. I liked hearing her moan softly, trying to keep them in. She started grinding on my face using my tongue to get off. I felt her legs start to shake, and heard her stifled moan. She was barely able to stay on her feet. I kept pressure on her clit with my tongue until he feet were solid on the floor again. Coming down from her orgasm, Amber looked at me and smiled. She pulled me to my feet and kissed me.

“You’re being such a good girl. Now I’m going to go out there and stand with Bethany. You are going to try on all of these dresses. Come out and show us each and every one.” I spent the next hour going in and out of the changing room trying on different dresses and showing the girls. They would either give me a thumbs up or down. I think I ended up trying on every dress in the store. We left that store with upwards of 30 dresses. We took all the shopping so far to the car and went back In. Amber said I needed some more comfortable and casual clothes.

We stopped by Lululemon and tried on every type of legging. Amber selected the ones she liked best on me and got multiple colours. We then went and bought shorts and jeans, and picked up shirts and hoodies in every store. Amber got every article of clothing I could think of, plus some I didn’t even know about before that dayb. Amber went the extra mile, buying every type of shoe I could ever want or need; from heels to flats, sneakers to flip flops. After 8 hours of shopping and trying on every manner of clothing we left the mall. The car was full of clothing bags. I couldn’t believe how much stuff we had got in one day.

When we arrived home we had to take multiple trips to get all the bags inside. As I brought the last bag into the bedroom, I noticed it seemed more empty than usual in there. I looked around and my shoes were gone. I looked in the closet and all of my clothes were gone. I checked the dresser and all my underwear and socks were gone.

“Amber! Where did all my clothes go? Did we get robbed?” Amber just laughed at me. “Hehe, no silly! I told my sister Stephanie that you were my girlfriend now and I was taking you shopping for a whole new girl wardrobe. So, she came by and took all your old stuff and got rid of it! You are going to live as a girl full time from now on. Oh and I also forgot to give you this.”

She reached into a bag that I didn’t recognize and pulled out a pink nub chastity cage.

“You will wear this all the time. I will hold the key and tell you when you can remove it. But all other times your little pathetic clitty will be locked.”

She threw it at me and I put it on. We spent the rest of the day hanging up all my new clothes and putting all the shoes away.

This is the end of part 2. The 3rd part of this series will is being written as you read this and will be uploaded soon! Thank you for reading!

It was a Friday afternoon and I had zero plans. My girlfriend was out of town and wasn’t due home for another couple days. So naturally I took the opportunity to get fully girlie. I hopped in the shower and shaved my body all smooth. I made sure to wash my hair and body with all of my girlfriend’s products so I smelled the part. After getting out of the shower I lotioned my body.

Then I moved to the bedroom, deciding I wanted to go the extra step and put press-on-nails on. I chose on a set that were almond shape and white. As I glued on the nails I knew my decision called for my toes to match. Returned to the bathroom, I rummaged around under the sink and found a bottle of white nail polish. I painted my toes and then did my make up while waiting for them to dry.

After I completed my full glam look I lowered my wig on my head. I picked out my wavy strawberry blonde one. I then moved to the closet to search through my girlfriend’s side, my girlfriend Amber was a very similar size to me. About 5”5’ and curvy in all the right places. I had tried her clothes before so I knew we were the same size clothes. I picked out a pair of her underwear. I selected a black lacy thong and a matching black bra. I selected a wine red long sleeve bubble dress. And to complete the look I put on a pair of black strappy heels. After checking out how I looked in the mirror, I felt proud of my self. Not seeing my self looking back at me, but instead the girl I longed to be.

Being all dolled up and not having any plan I decided I was just going to do some chores. I started with sweeping the floor. I made it to the kitchen sweeping when all of a sudden…

“WHAT THE FUCK! WHO THE FUCK ARE YOU?”

I froze. It was my girlfriend, Amber’s voice behind me, she wasn’t supposed to be home yet.

“Is that my dress? Are those my shoes?”

I still had my back to her. Frozen in fear. Unable to turn around and face her dressed like this.

“Bitch. I’m talking to you. Turn around and face me.”

I felt her hand as it grabbed my shoulder and spun me to face her. She had a look of shock on her face that matched my own.

“Babe? I thought you were another girl and you were cheating on me.”

She took a step back and looked me up and down. Taking it all in. Admiring all my hard work.

“So this is what you do when I’m not here?”

I nodded sheepishly. She stepped forward and hugged me. I was confused.

“You should have told me! You look beautiful! Do you have a girlie name you call yourself when you are dressed up?”

“Emilia,” I barely mumbled.

“Well here’s the plan, Emilia. If you want to dress like a girl your going act like a girl.”

I was confused with what she was talking about. She took my hand, lead me to the couch and made me sit down.

“Wait here. It’s not fair that only you get to dress up,” and with that she ran to the bedroom.

I waited on the couch still in shock at what was happening, replaying what had just happened in my head over and over again until I was snapped out of it by Amber standing in front of me. She was wearing an a-line black dress with fluffed tulle underlay, stockings, and black pumps. She had done her make up and curled her hair. She looked absolutely stunning. She sat on the couch next to me, taking my hand. Her other hand went to my cheek caressing it gently before forcefully pulling me in for a kiss. We sat on the couch making out our tongues exploring each other’s mouth. She was being more aggressive than usual but I liked it. She pulled out of the kiss, looked me in the eye and smiled.

“You look stunning. If you want to dress like a girl I’m going to treat you like my girl. Tomorrow we are going shopping to buy you a whole new wardrobe. But tonight I make you my little slut.”

With that she pulled me in for another kiss. As we were making out she pulled me on top, so I was straddled her on the couch. I climbed onto her lap and she started moving my hips so I was grinding on her. I could feel something under her dress. Breaking from the kiss, I looked at her with confusion in my eyes.

“What’s under your dress?” I asked curiously.

“Get on your knees, slut, and I’ll show you.”

I climbed off her and got on my knees in front of her just as I was directed. She lifted up the hem of her dress and that’s when I saw that she was wearing a strap on. It was 7” long. Again I froze now knowing the direction this was going.

“Suck it bitch,” she demanded. She grabbed the back of head and pulled me down towards it.

Running on instinct I parted my lips and let the dildo penetrate my mouth. I started servicing the dildo moving my head up and down doing the best I could to make it cum. As I continued to bob I could hear her start moaning. My movement over her cock was making the strap move and it rubbed against her clit. After 5 minutes of sucking she grabbed my head and stopped me. She grasped my hand and dragged me to the bedroom. When we got there she threw me on the bed and climbed on top of me. I wrapped my legs around her waist and my arms around her neck. We continued our passionate kissing as her hands explored my body I could feel the tip of her dildo pressing against my pussy through my panties. Her hand reached down and pulled my thong to the side. I felt her member start pushing against my eager hole. My pussy happily accepting her.

I felt her slowing entering me. A moan escaped my lips, flowing into her mouth. She pulled back smiling as she continued to push into me. Her eyes rarely left my face, watching my enjoyment as I moaned. When she finally got all the way to the base I felt completely full. She looked at me and flashed a mischievous smile as she began pulling back out. She slowly started thrusting in and out, increasing her speed as she went. Making me moan more and more. Louder and louder. She continued thrusting. There was a sudden change of space, she had nearly stopped, I looked up to see what had happened. Her body shook, she moaned, biting her lip as waves of pleasure swept through her body. The rubbing of the strap against her clit had just made her cum. As she came down to from her high she looked at me and smiled.

“I’m not done with you yet slut.”

And she began thrusting again. I could feel my own orgasm starting to build. She kept thrusting.

“I’m going to cum,” I yelled.

“Good girl,” Amber replied.

She pulled out of my pussy and wrapped her mouth around my clit. I erupted rope after rope into her mouth. After my balls were completely empty she took my clit out of her mouth and smirked at me. She reached out with her hand and grabbed my face forcing my mouth to open. Leaning over my body, she spit my load into my mouth.

“Swallow, good girls swallow the cum they’re given.”

I swallowed my load and Amber collapsed on top of me. She gently kissed my lips and cheek before she nuzzled her head into my shoulder.

“You make such a good girl, you will be a girl permanently now. Like I said before, tomorrow me and you are going to buy you a whole new wardrobe. Would you like that?”

I nodded, “yes please!”

We took off our outfits and makeup to go to bed. When I went to crawl into bed in my normal bedtime outfit, naked, Amber stopped me.

“Girls wear cute pyjamas to bed,” she instructed me. Then she threw a pair of pink satin pyjamas at me. I put them on and with that we went to bed!

And we leave this story here! There’s many more parts to come with Amber! Part 2 of the shopping trip will be coming out soon!

I had been crossdressing in private for as long as I can remember. If you want to hear more stories about my past or more in the future let me know! This story takes place when I was 26. And the first time I got fucked by a man.

I am a tiny human being. I’m barely 5’5” and 130 lbs. I was living in a small town and had never been dressed up out in public before. But I got fully dolled up multiple times a week to take pictures and live out my girlie life in the safety of my own home. Looking for the courage every time to take the step outside but never finding it. So there I was sitting at home on a Friday night, scrolling Grindr not looking for anything in particular but enjoying the attention. Being on Grindr in a small town it’s hard to find someone that you don’t already know or hasn’t messaged you before. Then my phone vibrated and his message popped up. The picture intrigued me like no other. It was simple. Just him shirtless. Just an average looking build but it caught my attention. His message, short and simple.

“I want you. Now”

Without thinking my thumbs replied, “Where are you located? Would you like to pick the outfit I wear?”

I had never done anything like this before. My brain was screaming What m I thinking? But my bored and horny self just took over.

He immediately replied “I’m at the hotel in town. Wear something sexy but comfy.”

In pure excitement I proceeded to get ready. I started by showering and shaving my body. Putting on lotion after to remain soft and smooth. I moved on to putting on make up, a full face of glam. Going all out for this mysterious daddy I was about to go and meet. Ending the make up with a bright red lipstick. I slowly placed my light pink wig onto my head and ran my brush through it. Then I went to get dressed for the adventure that lay before me. I started with a matching bra and panties set. I decided on wine red. The panties cute and lacy. I rolled on some thigh high black stockings to add to the sexy look. Then it was time to pick the outfit. I pick out a cute dual tone dress. A white top and black skater skirt that fell about mid thigh just long enough to cover the tops of my stockings. For my shoes I pick a pair of over-the-knee boots with a 4 inch heel on them. As it was late November I added a Jean jacket to keep warm as I ran to the car.

I admired myself in the mirror, loving the girl that was staring back at me. I walked downstairs and checked my phone. He had given me his room number, but asked me not to go in through the lobby. He had a room on the first floor and had a patio door, perfect, I thought, less of a chance to run into anyone I know. I grabbed my purse, walked to the front door and froze. This is the furthest I had ever gotten. The nerves were kicking in. I was panicking. Should I just message him and cancel? No! I’m tired of this. I need to push myself, and with that I opened the door and stepped out. The cool night air rushed around my legs and up my skirt hitting my pussy and clit sending a new sensation through my body. I looked around to make sure no neighbours were out. The coast was clear. That’s when I took a deep breath and ran to the car, basically diving into the drivers seat.

This is where next part of panic set in. I didn’t consider the 10 minute drive to get the hotel, but I was committed now. I turned the car on, threw it in gear and started driving. Driving in heels was a new feeling and something I got used to faster than I expected. Arriving at the hotel, I drove around to the back to where he said the room was. And then I saw him. He’s standing shirtless on the patio waiting for me. Seeing my car drive by he waved to me. I pulled into the parking spot and needed to hype myself up to get out of the vehicle. Am I really about to do this? Am I really about to go into this stranger’s hotel room for sex? I turned off the car and opened the door slowly. I got out and closed the door. Turning around to face his direction, my body just started walking. I got to his patio and he was there. On the other side of the railing. Face to face.

“Holy fuck. You look stunning” he said breaking the awkward silence.

I looked down at my shoes and blushed, barely able to squeeze out a quiet “Thank you.”

Looking up at him, I asked the obvious question, “Where’s the gate? How do I get in?”

“There isn’t one. You are going to have to jump the railing.”

So there I was. In public for the first time, faced with a dilemma. I could have turned and ran (as good as I could have in 4 in heels) or I could attempt to jump this waist high railing in my dress and heels. Fuck it, I thought, and looked around to find something to help me jump over. On the side of the patio was a giant rock half buried in the ground and I seized my opportunity. I climbed onto the rock and it gave me just enough height to throw one of my legs over the railing. It is at the point that I realized that I just flashed this man everything I had to offer. And the look on his face confirmed it. I finally managed my way over the railing. There I was, face to face with the person I had gone to see. He wasn’t much taller than me in my heels, an average build, generic looks.

“Holy fuck. You are gorgeous” he said as he reached out to pull me in close. As I leaned into the hug he took the chance to kiss me. There I was. At a hotel. Kissing a man. For the very first time. Dressed to the nines. Something I could have never imagined I would actually do. As our tongues intertwined I felt his hands exploring my body and slowing making their way down over my skirt. He squeezed my ass with such force it pulled me up onto my tip toes and I let out a small moan into his mouth.

“Should we take this inside?” I asked him, and he nodded enthusiastically. He grabbed my hand and lead me through the sliding glass door. Once inside I took off my jacket and put it on the chair with my purse. When I turned around he was right there and pulled me in for another kiss. Standing in the middle of the room making out, I could feel his manhood growing in his pants pressed up against my equally swelling clit. As his hands explored my body and ass, my hands explored his, slowly make their way to grasping his rock hard dick through his pants. As I fumbled trying to get his pants off he lifted up the hem of my skirt to get a better grip on my ass. I finally got his pants down and I felt the head of his cock stabbing my stomach. There I was, faced with the first cock I’d seen that wasn’t mine. He wasn’t much bigger than myself; A little over 5 inches. I reached out and took it in my hand. I don’t know what I was expecting, but it was softer and warmer than I had previously imagined. I started stroking him while our tongues were still intertwined. After a few moments the temptations took over. I pushed him back onto the bed and dropped to my knees in front of him. Face to face with a cock for the first time. I grabbed the throbbing cock in front of me, looking up I found him looking down, staring back at me, waiting for me to take him into my mouth.

I slowly leaned forward and licked his head. The taste was intoxicating. I slowly started taking him into my mouth. The feeling was unlike any dildo I had sucked before. Softer, warmer, and firmer yet yielding. As I had him in my mouth I start licking around the head, and I heard him start to moan. I must be doing something right! I slowly start to bob my head up and down my lips wrapped around his cock. I felt every vein and bump as I went. He reached out and put his hand on the back of my head and started to guide my rhythm. This continued for a couple minutes. Moving up and down his shaft and stopping to lick the head before going back to bobbing up and down his length. He stoped me by pulling my head up, bringing my lips to his own. He pulled me to my feet and told me to lay on the bed next to him. He lifted my skirt up and released my own member from my panties. And started to stroke it. We stroked each other while our mouthes explored one another’s until he got up and climbed on top of me to 69. He slides his dick back in my mouth while taking me into his. I tried to suck his dick to the very best of my abilities while having barely any room for my head to move.

I removed his cock from my mouth and my words fully bypassed my brain. I blurted out “Please, fuck me daddy!”

He jumped up and was like a dog with a bone. He slid my panties down past my ankles and threw them on the chair where I had set my things and reached for the bottle of lube on the side table. I stood up and bent over the bed so he had better access to my eager hole. He lubed up his dick and then I felt him starting to lube my ass. I felt his fingers moving around my hole. Then I felt him slide one in. Then two. I felt the fingers leave and then the head of his penis started pushing against my hole. I couldn’t wait anymore. I pushed my hips back into him as he began moving forward. My hole gave no resistance and this man went from not in me to balls deep into my ass in 0.5 seconds. I was hit with a wave of extreme pain. I cried out and tears rolled down my face. He pulled out and immediately started apologizing. I told him it was alrightalr and I just needed a second. Once I regained my composure I got back onto the bed and laid down on my back. He climbed in between my legs and we tried again.

He went slower this time and instead of intense pain I was met with immense pleasure as he entered me. I moaned as he slowly put his entire cock into me. Once his balls hit my ass he started to slowly thrust. I felt the pleasure building within me. I was unable to hold back my moans. As he started to pick up his pace he slowly began to rub me with the same tempo. My continued moans lead him to fuck me harder and faster. I could feel the orgasm building within me. And then it hit. An intense orgasm. I explodedxpplod all over my stomach and the inside of my dress that was only pulled up far enough to be out of the way. My legs shook and I was unable to comprehend what had just happened. He yelled that he was about to cum and he pulled out eruptederrupte all over my softening dick and stomach. As I slowly came down out from the glow of my orgasm I felt his hand wipe across my stomach. Looking down I saw he is scooping up the puddles of our mixed pleasures with his fingers. He then reached out and put his cum covered fingers in my open mouth that was grasping for air, feeding me both of our loads. I swallow all the cum he gave me. I headed over to the bathroom and cleaned the rest up. Walking out of the bathroom I kissed him one last time. I thanked him for an amazing night and slid my panties back on, then put my jacket on and left.

And that’s the story of how I fucked a man for the first time! Let me in know if you would like to hear more of my stories.