New! A Night to Remember

I wish to thank Annabelle Brito for reviewing and making suggestions that have greatly improved the story. The characters are the from my perverted way of thinking.

This is complete fiction and any resemblance to persons living or dead is pure coincidence. I hope you enjoy it. Please leave your comments, good or bad. I try to learn from constructive criticism. If you prefer you may email me at kjensen0611@gmail.com.

A Night to Remember

A guy is lured into a 1970's sexy disco outfit by his girlfriend! But finds out some shocking secrets about her and a new side of himself all in one night. 

Sara and I had been dating about 6 months. She was kinky and funny and kept me laughing most of the time when I was with her. She had short black hair and the most amazing green eyes which I could get lost in. She was about 5’8” which made her an inch taller than me. While her tits weren’t huge, they were perky and stood out even without a bra which she often went without when we were together. Going braless made her feel more free and comfortable. She also knew how I loved it when her nipples protruded from her sweaters. 

She lived at home with her step-father. Her mom had run off a few years earlier and Sara flatly refused to go with her, hating the guy her mom ran off with. Steve, her step-father was pretty cool and easy going. He was fairly young, not even 40 yet, and had made a ton of money selling his software company. 

Sara was very self confident and quite dominant. I loved her so much that when we did have an argument I almost always gave in not wanting to feel her wrath. When I didn’t give in, she would go off in a huff and it might take anywhere from an hour to a couple of days before we made up. But I almost always apologized and we always did make up.

When we were having coffee at one of our favorite spots we ran into a friend of hers. She came up to Sara and hugged her both giddy with joy. I guessed they haven’t seen each other in a while. Sara introduced me as her boyfriend, but she didn’t mention her name. Both then went to the bathroom together leaving me alone with my phone.  

“Who was that?” I asked. 

“An old friend, I got some exciting news,” she said. “We were invited to a party!”

Apparently it was a disco costume party. That’s right, we were all to come dressed like we were going to a disco dance of the 70s. Sara decided that we should cross-dress. I would go as the girl and she as the boy. Cross-dressing was not my thing and I told her that. 

“Come on, it’s all the rage right now! Many couples are doing it. Celebs are doing it too. People are way more open about it.”

“Aeh…I know, I mean. C’mon…its just not my thing. Can we just stay in that night?”

Sara does not take no for an answer and without saying another word got up and left me sitting there in the coffee shop. Two days later we made up, but only when I agreed to go to the party dressed like a girl. I just couldn’t imagine her having her out of my life.

When Sara decides to do something she goes in all the way. It should not have been a surprise when, on the day of the party, she rang my bell, dragged me out of bed and took me to a beauty salon. Despite my protests I was first subjected to a full body waxing and I mean full body. No hair was left beneath my eyebrows and even they were waxed leaving them with a decided feminine appearance. My shoulder length hair, which I normally kept in a pony tail, was washed, blonde streaks were put in it and a wave was added to it along with a hair band. My nails were filed; acrylic nails were attached and polished with a hot pink polish. My toenails were filed and the same pink polish was applied to them. I was given a mudpack facial and then a complete makeover ending with pink lip gloss to match my nails.

The owner, a big lady, then took me by the hand and literally dragged me to a back room. I saw a dress hanging on a hook in the room. I assumed it was for me and I cringed when I saw it. It looked to be incredibly short.

“Come on, robe off, everything off. I will dress you for the party.”

I made the mistake of refusing. 

 “Wait, where is Sara, I changed my mind.”

“Hurry up, nothing to be ashamed of, I already saw you naked when I waxed everything off!” 

“No, I’m outta here..I-“

 “I know how to deal with sissies like you!”

The next thing I know I was across her lap and being spanked with the robe pulled up and my boxers pulled down my bare recently waxed butt on display. I don’t know how long she spanked me but she stopped only when tears were running down my face and I begged her to stop and agreed to allow her to dress me. 

“I anticipated this and had the girls use waterproof makeup. So if you agree to be a good girl I will give you the makeup remover. Otherwise it will take a couple of weeks to wear off. Do you understand?”

I nodded.

“Say it!”

It was embarrassing, but I said “I will be a good girl.”

She handed me a couple of tissues to wipe my eyes. 

“Now strip!”

I did not hesitate and quickly removed the pink robe they had given me when we arrived. I stood there in just my boxers, but she motioned with her hands for me to remove them as well. I was not about to let her spank me again, so they too came off.

“Good girl!” she said embarrassing me further.

She picked up a white garment from the chair and told me to face away from her. She then wrapped it around my waist, explaining that it was a waist cincher. She laced it up tightly until I could hardly breathe. It had four garters hanging from it. She told me to take shallow breaths. She handed me a package of white fishnet stockings and explained how I was to put them on, warning me of the consequences of running them while doing so. I successfully got them on and with her help attached the stockings to the garters.

Then she handed me a pair of lacy pink bikinis. Before I got them up all the way she stopped me. She then manipulated my balls up into my body and pulled my dick back between my legs where she taped it.

“This will prevent you from having any unsightly bulges in the front of your dress and you will still be able to urinate, but you will have to sit like the girl you are.”

She wrapped a padded pink bra around my chest and hooked it. Then she had me step into the dress and zipped it up the back. I felt imprisoned in it knowing it would be difficult for me to remove. The final item was the boots. They were white with a 3 inch block heel. It took me a few moments to get accustomed to the height, but with a bit of practice I could actually walk in them. 

Up to this point I had not seen what I looked like. She stood me in front of a full length mirror. I was stunned. Not only did I look like a girl, but I looked like a very pretty girl. I was amazed to say the least. I also realized that the dress was so short I would have a problem not displaying my panties to the world.

Just then the door to the room opened and a man walked in. At least that is what I thought at first glance.

He looked at me and gave me a big grin.

“You look amazing” he said.

“Sara?”

“Who else? Come here doll!”

I walked up to her and she gave me a big hug. Though I had on 3 inch heels, she too was wearing heels and we were now the same height. Taking the lead she kissed me, plunging her tongue deep into my mouth. She gave my ass a squeeze while she kissed me. I could feel myself trying to get hard, but unable to because of the tape it only frustrated me.

“Are you ready to disco?” she asked me.

I was still embarrassed at the prospect of appearing in public dressed like a girl, but encouraged by what I saw in the mirror, I nodded. She took my hand and led me out of the salon to her car. 

“So Marc, or maybe I should call you Marci, how was your day at the spa?”

I was too embarrassed to tell her about the spanking so I merely said “It was ok”.

“Good. I hoped you would enjoy being pampered.”

She held the door of the car for me and then walked around to the driver’s side.

“I think you flashed your panties to those guys standing at the corner when you got into the car.”

I looked over towards them and they were smiling at me causing me to blush.

“Let’s get out of here, please Sara” I said.

“Whatever you want princess, but for tonight you may call me Stan.”

She was enjoying my discomfort at being dressed like a girl and I was not happy about it. I was about to get even more unhappy when she pulled up to one of our favorite restaurants. 

“What are you doing?”

“I’m taking my best girlfriend to dinner” she smiled.

“I’m not really hungry. Can’t we just go to the party?”

“I am hungry. I haven’t eaten since breakfast and in any case it is too early to go to the party.”

The passenger door was opened and the valet held his hand out to help me.

“Just get out Marci and come. It will be fine.” She ordered.

I tried to keep my legs together so as not to flash my panties and hoped I was successful as I got out of the car. I did not look at the valet’s face to see if he was enjoying the view. Sara got out on the driver’s side and handed the valet her keys. Then she took my hand and led me into the restaurant.

We walked up to the hostess and Sara asked for a table for Ryan. The hostess, who knew us well, looked at us with surprise.

“Sara? Is that you?”

“Guilty as charged.”

“Why the getup?

“Costume party later this evening.”

“This can’t be Marc, can it?”

“Yes it is, but tonight we are Marci and Stan” she grinned. 

I cringed and felt my face get red.

“You both look great. I don’t think anyone would recognize either of you.”

She grabbed a couple of menus and led us to our table. There she held my chair waiting for me to sit while Sara...Stan stood also waiting for me to sit.

With that uncomfortable situation behind us, and Sara speaking in a lower voice ordering for both of us, we had a pleasant meal and no one seemed the wiser to our real genders. The real issue came at the end of the meal when I realized I had to pee.

“Well go to the bathroom. What is the problem?”

“I can hardly go to the men’s room looking like this.

“Go to the ladies’ room, remember to sit and wipe yourself when you’re done. It is not that hard.”

Nervously I made my way to the ladies’ room. And wouldn’t you know it, there was a line. I stood there and, of course, the woman in front of me had to make conversation.

“Why are you dressed like that?”

“Costume party” I answered in a low voice that I hoped was feminine enough.

“You are very pretty. Have fun!” she said as a stall opened up for her.

Finally we were able to leave the restaurant and head to the party. By the time we got there it was in full swing. Everyone was dressed for disco and as far as I could tell we were the only cross-dressed couple which predictably, made me nervous. When we got there Sara excused herself to go to the bathroom. No sooner did she leave me then some guy came up grabbed my hand and pulled me to the dance floor. We danced a couple of dances when the DJ said he was going to take a 15 minute break. I looked around for Sara but could not find her. The room was crowded and she could have been anywhere.

My partner said something to me but I missed it.

“Speaking softly in what I hoped was a feminine voice I asked what he had said.”

“Would you like a drink?”

“Yes, that would be nice.”

“I’m Brad.”

“Marci, nice to meet you.”

He grabbed my hand and led me over to where the refreshments were. I was getting nervous, unable to find Sara. 

“What’s your pleasure Marci?”

“Water please” I was too nervous to drink alcohol.

“Nice party, huh?” he said.

“Yeah” I answered. 

I really did not want to have a conversation. I was afraid the more I talked the more likely it would be that I would be recognized as a guy.

By the time the DJ came back I still could not find Sara and before I knew it I was dancing with Brad again. I was getting more nervous by the minute. His hand did stray a couple of times and squeezed my ass. I really did not know how to deal with it so I let it pass. It did not take too long before I was tired and I motioned to Brad that I was going to find a seat. Unfortunately he followed me over and sat down next to me. This is what I dreaded. He told me about himself and cracked a couple of jokes that made me laugh. I was starting to feel more comfortable with him and responded by telling him about myself, I hoped without revealing my true gender. I must confess that despite my nervousness, I was having fun being taken for and being treated like a girl

It was then that Sara appeared. I don’t think I was ever so happy to see anyone.

“Brad, this is my boyfriend, Stan.”

Actually I’m his girlfriend. My name is Sara and his is Marc” she said pointing to me.

“You’re a guy! You sure fooled me.” He smiled and said “Too bad.”

I was relieved he was not angry over my deceit.

“Well, have fun you two!” he said. 

Then he kissed me on the cheek and headed off.

 “You heartbreaker you” Sara said.

“Not funny! If he had taken it wrong I could have been hurt. I could have been hurt badly. I have been looking for you the whole time. Where have you been?”

“You seemed to be enjoying yourself. I didn’t want to spoil your fun. Let’s dance!”

 “I don’t want to.! Let’s get out of here!”

I stomped off towards the door. Fortunately she followed me. In the car we argued and before I knew it we were at her house. We were still arguing as we walked in.

“I’ve had it with you” she said. “You sure were acting the part, flirting with him, and enjoying yourself.  I’m going to bed, without you. You are on your own.”

She walked off to her room, slammed the door and locked it.

The argument was in front of Steve who was lounging on the sofa with the aroma of pot in the air. He looked at us but said nothing. There was something about Sara’s tirade that was off, but I was too upset to think about it. I always hated it when she got angry with me but this seemed different. I feared we were on the verge of breaking up. I felt myself starting to tear up and headed for the bathroom. While there I sat down to pee. When I realized what I was doing I ripped the tape off. It felt good to release my cock and balls. When I pulled up my panties I had a huge erection which was painfully obvious when I adjusted my dress. I really wanted out of these clothes but the only clothes I had in the house were in Sara’s room. 

I knocked on her door and called to her.

“Please Sara! Give me my clothes. I can’t go home in a dress.”

“Call your boyfriend and ask him to take you home. Now leave me alone!”

I knocked on her door a few times but she did not respond. The thought of losing her was bringing me to tears.

Steve appeared next to me. He gave me a handkerchief to wipe my eyes. Then he put his arm around my shoulder and headed me towards the living room.

“You know how volatile she is. She will be forgiving in the morning.”

I looked up at him and thanked him.

 “I hope so but in the meantime I need to go home but I can’t go in these clothes.”

“Why don’t you sit down, you had rough night.”

“Thanks, I guess I did…” I said as I sat down.

“You ever smoke a little herb Marc?” 

“Uhmm…yeah sometimes,” I said unsure of myself. 

 “Good, we’ll smoke a joint and worry about it later.”

We sat next to each other passing the joint back and forth. I was getting mellower with each hit and by the time we finished the joint we were both very high.

He looked over at me.

“Can I tell you something Marc?”

“Sure”

“I hope you don’t mind me saying this, but you are one foxy lady!” he said. “I know you’re a guy, but Sara dressed you so sexy.” 

“Huh” was all I could say.

“I want you.”

I’m sure if it was mostly the high from the pot, but his words of desiring me and the sensuous feel of the clothes were turning me on and I still had a huge bulge which my dress couldn’t hide.

I smiled at him. “So what are you waiting for?” I said seductively.

He smiled back at me and slid over right next to me. We looked at each other with smiles on our faces. He leaned over and kissed me gently on the lips. It was nice and I leaned him to him, grabbed his face with both hand, pulled him to me and returned the kiss with far more passion. I felt an electric charge go through me like I had only felt with Sara. I desperately wanted to feel it again.

He took my hand, helped me to my feet and led me to his bedroom. I did not understand why I was letting this happen but I was so turned on I went with the flow. He kissed me again my cock strained against the tight panties I was wearing. He unzipped my dress and let it fall to the floor. 

Then he lifted me and gently placed me on his bed on my back. He pulled off my boots. Then he pulled my panties off, leaving me only with my bra, corset, and stockings. He undressed himself leaving me with a good view of his erect cock. He then lay down next to me. By now I was leaking pre-cum and I had not touched myself. He licked it off and kissed the head of my cock.

“You have a pretty little clitty and you taste so sweet” he said.

I am a guy and I should have been insulted, but his comment only turned me on more. Then he took my cock in his hand and stroked it. He licked my balls. I was trying to hold back but he was a master and I knew I wouldn’t last long.

“I’m gonna cum!”

He stopped stroking me, looked up at my face and smiled.

“Whenever you’re ready just feed me your sweet nectar”

Then he leaned over and took me in his mouth. He licked my shaft a couple of times and deep throated me before I exploded into his mouth. He swallowed it all. When he had sucked all of it out of me he crawled between my legs, leaned over, and kissed me. I tasted my cum on his tongue and lips. He rolled over on his side and took a tube from the night table. He squeezed some lubricant from it and played with my ass. I had never engaged in ass play before and was surprised at how erotic it was. Despite having just cum I could feel my erection starting again.

He inserted one finger in my ass and moved it around. Then he inserted another and I was once again erect. I could not believe how good it felt to have his fingers enter me there.

“Now I am going to make you my girl” he said.

He rubbed lubricant on his cock and once again crawled between my legs. He lifted them onto his shoulders elevating my ass slightly off the bed. He rubbed his cock on my opening. I was gasping at how incredibly exciting it was. Then he slowly inserted it into me. At first there was some pain, but he was gentle and stopped frequently. 

“Just breathe deeply” he told me.

It seemed to help and he continued his penetration. Before I realized how far in he was I could feel his balls swinging against my ass. Then he slowly withdrew until only the head of his cock was inside me. I felt empty. I wanted him all the way inside. He repeated his actions slowly, penetrating and withdrawing. 

I moaned and gasped as his hard cock pounded into my virgin anal hole. The pain turned to pleasure and I felt that I would cum again. Gradually he speeded up. He let out a few grunts as he fucked me hard. All I could do was grip the sheets tightly and moan like a common slut during his thrusts into me. I could feel him tense up and I knew he was about to cum. As I felt his hot load enter me filling my insides I also came, ejaculating all over myself. When his spasms stopped, he slowly withdrew out of me and lowered my legs back onto the bed. Then he rolled onto his side next to me.

He surprised me by picking my semen off my belly and chest with his finger and feeding it to me. Caught in my post orgasmic glow I swallowed it and enjoyed it. He smiled and kissed me on my forehead. When I had eaten all of it he rolled me onto my side, pulled up the blankets and spooned me from behind. We fell asleep in that position, covered in sweat and me filled with his fresh warm semen. 

When I woke up Steve was gone. I still had on my bra my waist cinch and stockings, my once virgin hole felt used and I had to pee badly.  I went to the bathroom, put the seat down, pulled down my panties and sat on the toilet like a girl. As I sat there I wondered why I did that. Was it the weed? the alcohol from the club? or was it because Steve had gotten me in an emotionally vulnerable moment? As I washed up I looked in the mirror and realized I still had on the makeup. I tried to wash it off but was unsuccessful. 

When I returned to the bedroom I found Sara lying on the bed. She was smiling at me. I was embarrassed standing before her in my girlie underwear, but she was unbothered by it. She walked up to me and kissed me passionately.

“So did you have a good time with Steve last night? I heard all your passionate screams last night,” she said. “I can tell you two had quite a night by the look and smell of the bed sheets. Not to mention of yourself, you smell of hot sex”

I felt embarrassed and guilty and said nothing.

“I’m sorry Sara. I don’t know how I could have done that. It must have been the weed”.

“It’s ok” she said and kissed the top of my head. “In fact, it is better than ok.”

“What do you mean? I don’t understand.”

“Let me help you out of your clothes and you can take a shower. I will leave clean clothes on the bed while I make breakfast. We can talk then. Is that ok with you?”

I nodded. Clearly there was more than meets the eye going on here.

She unhooked the stockings from the garters and knelt on the carpet. She pulled the stockings off my legs. It was very erotic and I got hard instantly.

“No time for that now! Maybe later.”

She loosened the waist cinch and removed it from me. Then she unhooked my bra and took it off. 

“I think you can handle the rest while I fix breakfast. I imagine you are very hungry. I know I am.”

 “I have makeup remover. Do you want me to remove your makeup for you?”

I nodded, still not understanding how she could be so friendly after our row the night before.

She removed my makeup, I took off my panties and headed for the shower. I luxuriated under it while I tried to figure what was going on. After drying myself I went back to the bedroom expecting to see some of the clothes I had left at Sara’s. Instead I found panties, a padded bra, a package of pantyhose, an A-line corduroy miniskirt and a short sleeve sweater. On the floor was a pair of sandals with about a 2 inch block heel.

“Sara” I called to her.

“Just put on those clothes and I will explain everything or, you can come out here naked.”

“Just give me my own clothes. Please!”

“No! Do as I say!”

My whole relationship with her it seemed was obeying her wishes when we disagreed. Reluctantly I put on the clothes. I had seen her dress often enough to know to hook the bra in the front and spin it around.  I looked in the mirror and was disturbed to see how feminine I looked. I could almost pass for a girl even without makeup.

Sara was just putting breakfast on the table when I came out. She looked up and smiled at me. Steve was also there. He was smiling at me. I could feel my face turn red. I don’t know why I felt so embarrassed standing there dressed as a girl after the previous night.

Steve stood up and pulled out a chair for me as if I really were a girl. Not knowing what else to do I played along and sat, remembering to spread my skirt under me and feeling like such a sissy.  He kissed my cheek before returning to his own chair. There was a dynamic unknown to me here. I assumed I was about to find out what it was.

“You are a pretty girl” Sara said.

“Thanks, I guess. I’m not sure that is something any guy wants to here.”

“Dig in and we will tell you what is going on. First off I need to apologize to you Marci..er Marc. I, actually we have been using you, but if you agree to our proposal this could be good not only for you, but for all 3 of us.

“Using me how?”.

“Steve is not my step dad. He is my lover.”

She turned and smiled at him.

“We have been together for almost 2 years now. Though I have been using you, do not think I don’t care about you. I love you also and that is why this all happened.”

“I don’t understand” I said.

Steve took over.

“I am bisexual. I like girls and girls with something extra, if you know what I mean.”

“I..I think so. You mean like I was last night.”

“Exactly. I also enjoy anal sex which is not something Sara is into.

I blushed as I remembered last night. Sara smiled at me and I realized she knew what had transpired between Steve and me.

Sara spoke.

“We have been looking for a ‘girl with something extra’ for almost a year. The first time I saw you I thought you had the possibility to be that girl if you were willing. When I introduced you to Steve that first time he agreed. We were not going to rush into it. When I realized I was falling in love with you I almost ended it, not wanting to hurt you, but Steve felt we could make it work to all of our advantages. We were going to wait until Halloween to get you into skirts, but then I spoke to a close friend of mine about my fantasy and she came up with the plan to hold a disco party. We could use that opportunity to show you off to Steve as a sexy young woman." 

It was Steve’s turn to speak.

“Here is our proposal. You move in and live with us. I am very wealthy so there is no need for either of you to work. I travel frequently. When I am not home you and Sara are free to do what you want. When I am home I expect both of you to sleep with me. If I am right, you enjoyed making love to me last night and I believe you enjoy being with Sara. The kicker is you will have to live fulltime as a girl. Sara will teach you how to be a girl although you got off to a great start last night. You will  have to agree to undergo hormone therapy. They will be low doses that will cause breast growth and other feminizing effects. They will be administered by a licensed physician and will be completely reversible should you decide to leave us and live as a man again. You will still be able to function as a man. Sara would not have it otherwise. We don’t expect an answer right now. We want you to think about it. If you try it for a year I will establish a trust fund for you that you may take with you. It will be yours whether or not you decide to stay with us.

He handed me a piece of paper with a dollar figure on it. I thought my eyes would pop out of my head when I saw it. 

“Are you serious about this?”

“I am. I have already established such a fund for Sara with an equal amount.”

I looked over at Sara. She smiled and nodded at me.

Sara said “I have come to love you and I know you love me. My life with Steve has been far better than I could ever have imagined. The only way it could be better would be if you were also a part of it. This is the only way you and I can be together.”

“That is a lot to think about.” I said.

“You are welcome to stay here for awhile and experience the lifestyle you will have. It’s sort of try before you buy. If you want to go home away from us to decide we will give you your own clothes back. I think you know what I would like you to do. If you stay here while you decide you will have to do so as a girl”.

Sara broke the ensuing silence and told us to eat before the food got cold.

EPILOG – 1 year later

Steve signed over the trust fund to me. It had been an exciting year. I had not worn pants the whole time, only dresses or skirts and blouses. I had the most sexy and luxurious lingerie and found that I loved being a submissive girl to my lovers. Steve traveled at least a third of the time which gave Sara and me a lot of time together. When Steve was home the three of us slept together all of the time. I did have two weeks alone with Steve when Sara went home to see her mom. Those two weeks we had sex every night and morning. Everyday he would He treated me like his daughter during the day, but at night I was his lover in bed. I had never thought of being with another man, or should I say any man since I could no longer think of myself as a member of that sex. But I simply love being with him and having him treat me as a girl, his girl. Oh, I still have my penis. That is not going away and both Sara and Steve get pleasure from it as I do.

END