Flapper

Karen Jensen 

Clare and I had been together for 8 months and for the last month I had been living with her after I lost my job. As an attorney she made pretty good money, far more than I had been making as a clerk, but it didn't seem to bother her. I had hoped a college degree would buy me more than that, but there wasn't much call for sociology majors without an advanced degree, and the money for grad school was not available to me. And now being out of work, my debts were piling up and there was no job in sight. Clare was not pressuring me for my share of expenses and seemed happy to have with her.

The sex with Clare was incredible. She was very aggressive and far more experienced than I was, but that didn't seem to bother her. She was not hesitant to pull my pants down, drop to her knees, and give me the most incredible blow job. Other times she would push me back onto the bed and plant her pussy on my face and hold me down until I satisfied her multiple times. She was quite strong and in that position I was truly at her mercy. When we did have intercourse, it was only after I had satisfied her orally. She claimed that she couldn't orgasm from straight vaginal penetration.

She came home from work one night really excited. Her firm was having a Halloween party and she wanted to go. It was a costume ball to be held at a local hotel and all employees and clients were invited.

"I don't know Clare. I've never been that enthusiastic about these kind of things."

"Come on Eric, we can't sit home all the time and fuck, as much fun as that is. We need to get out. And we've never even gone dancing."

"We can go dancing, but it doesn't have to be at that party. I don't want to wear a costume and, in any case, I wouldn't know what to wear."

"Don't worry about that. I will take care of the costumes and everything else. All you have to do is get dressed and come with me. Puleeeze!"

"I will think about it," I replied hoping she would forget about it.

The next night she came home as I was getting out of the shower. She walked into the bedroom and before I could even put on my shorts, she pushed me back onto the bed. She practically nosedived for my cock and I could feel her tongue running up and down my shaft. In almost no time I was as hard as I ever had been. She teased me with her tongue, licking my balls and running it up and down my erection without ever taking it into her mouth.

"Please Clare, take me in your mouth and finish me."

"So you want to cum, do you?"

"Yes, please. I am so close."

She took me in her mouth and sucked, pulling away and squeezing my cock with her hand just as I was about to explode. I was so close.

"What will you do for me if I finish you?"

"I'll do anything you want. Just do it!" I replied thinking she would want me to eat her as I usually had to after a blow job.

"Anything?"

"Yes!"

"Even go to the costume ball?"

"Yes, yes!" I replied without really thinking about it.

With that she removed her hand from my cock sucked me hard. Almost instantaneously I erupted in her mouth. Clare was not one to pull away and would swallow whatever I gave her and this time was no different, or so I thought. She climbed on top of me and instead of placing her pussy on my mouth she leaned over to kiss me and with her tongue pushed a mouthful of my own cum into my mouth. She held her mouth on mine and with her on top of me I was helpless. I had no choice but to swallow it. I felt humiliated, but she just laughed at me.

Before I realized it she had pulled off her panties and was face sitting. After several orgasms she lay down next to me. We snuggled up and kissed, which was a normal part of our lovemaking.

The next morning she accosted me with a tape measure as I stepped out of the shower.

"What are you doing?"

"Taking measurements, so I know what size costume to get you."

"I can tell you my sizes."

"Costumes may be sized differently. I want to be sure so hold still."

The whole idea seemed ridiculous to me. I couldn't fathom why she couldn't just accept my word that I knew my pants and shirt sizes, but I had agreed to go so I stood there naked while she measured my waist, my chest, my hips, the length of my torso and legs. Then she looked up at me, smiled and winked at me, and then too my embarrassment she measured my penis. I should point out that I was not endowed with a particularly large one, and Clare never complained about it, but still, having her know the exact size was somehow belittling. She did not offer any comment, but when she was done she kissed the head before rising to her feet and telling me I could dress.

Nothing further was said about until the day of the party. She left our apartment after breakfast to pick up the costumes and returned several hours later, with bags that indicated she had been shopping, one of her favorite pastimes. After giving me a quick kiss she told me to come with her to the bedroom to see the costumes. At this point I had no idea what they were.

She opened one garment bag which had a double-breasted, striped jacket with matching slacks. a black shirt with a white tie, shiny black shoes and a black fedora. I thought I would like quite debonair and was pleased with her choice of costume.



From the other garment bag she produced a sleeveless, pink, fringed, flapper dress. I immediately pictured Clare in the dress.



"Clare, you will be the prettiest girl there in that dress."

"No I won't. But you might be!"

"What?"

"The dress is for you, along with the underwear in this bag and these shoes."

She pulled a shoebox from another bag and handed it to me.

"I don't understand."

"It's really quite simple Eric, or should I say Erica? Tonight I will be the gangster and you will be my girl!"

It took a moment for her words to sink in, but when they did, I refused to go along with her.

"No way am I going to dress like a girl!"

"You left the choice of the costumes to me. I picked them out, got them, and now you will wear what I brought home for you!"

"I am not going to the party in a dress!"

"Are you breaking your promise?"

"Yes, if it means wearing a dress!"

"In that case, pack your things and get out!"

"What? You can't be serious. You're going to end our relationship over a costume?"

"If I can't expect you to honor your promises to me, then I have to assume I have misjudged you and I don't want to be a part of this relationship any longer! So, Eric, the choice is yours. What will it be?"

The last thing I wanted was to lose Clare over a silly costume. I loved her and wanted desperately for us to work as a couple.

"I don't want to end it. I love you Clare, you know that. I will wear the costume."

She clapped her hands and gave me her big smile that I loved. Then she wrapped her arms around my neck and kissed me.

"Ok, we need to start getting ready. Strip!" She ordered me.

"But the party isn't for 5 hours."

"It will take that long to turn my handsome boyfriend into my gorgeous girlfriend. Now take off your clothes."

After undressing she took me into the bathroom, opened up a bottle with some kind of gel and proceeded to apply it all over my body covering every inch below my neck. It had an acrid odor.

"What is this stuff?"

"A depilatory that will remove your body hair."

"Why are you doing that?"

"Because tonight you are a girl. Don't be such a baby about it. It will grow back."

I was not real thrilled with the idea of being hairless, but did not want to make an issue of it. After her earlier threat of ending our relationship, I decided to play along with her tonight.

After about 15 minutes, she allowed me to rinse off and watch all my body hair go down the drain. Then she ordered me to wash with her shower gel which smelled like lilacs, a scent I loved on her, but was less than excited about smelling like that myself. After drying myself she powdered my body with, you guessed it, lilac scented bath powder.

She led me back to the bedroom where my costume was laid out on the bed. Everything was pink. I was to be dressed from the skin out as a flapper girl from the 1920s. My fear of Clare throwing me out was all that kept me going. I just knew I would never get over the humiliation I was already feeling.

The first piece of clothing she picked up was a corset, which she wrapped around my waist and proceeded to tighten. It was under the bust with hook and eye closure in the front and laces in the back. It had 4 garters; two in the front and two in the back. By the time Clare tied it off I was having trouble breathing. Her advice to take shallow breaths helped and I gradually found myself becoming accustomed to the tightness.

She then wrapped a bra around my chest. It was padded to an A cup. It was pink with a floral design on it and quite pretty.

"While the style of the 1920s was for a boyish figure deemphasizing bust and hips, I think the hint of breasts will help sell your disguise. Don't you agree, Erica?"

I did not miss her feminization of my name, but chose to ignore it and nodded. The humiliation I was feeling was growing exponentially. She had me sit on the edge of the bed while she rolled silk stockings up my newly hairless legs. The feeling was quite erotic and I soon had a raging erection. She seemed to ignore it while attaching the stockings to the garters on the corset. But after attaching them she smiled at me and said "well it looks like little Erica is enjoying herself. Wait till you put on these panties."

I tried to tell her it was because of her touching me that I had an erection, but she was clearly not convinced and I knew, but wouldn't admit it, even to myself, that that was only a part of it. Then she had me step into a pair of silk tap panties with lace trim on the legs. I was so turned on I thought I would cum right then, without touching myself.

Clare smiled at me and said "we better take care of that before you ruin your pretty panties."

She pushed me back onto the bed, pulled my panties down to my knees and went to work with her tongue and mouth. It didn't take more than about 10 seconds for me to explode. I ejaculated 3 good loads into her mouth. It was over quickly, but was incredible. I was not terribly surprised when she kissed me and deposited a load of cum into my mouth. I wanted to return the favor to her, but she told me there would be time for that later. Now she wanted to finish dressing me and then get into her own costume.

Next she had me lift my arms and she dropped a slip over my head. It too was silk, and if I hadn't just orgasmed, I probably would have right then and there. Clearly, the female clothing was turning me on and it was a bit disturbing. I had never had any thoughts or desires to crossdress, but I couldn't deny how erotic it was.

My hair was still wet from the shower and she took advantage of that to style it as a flapper would wear it. She trimmed it and then put hot rollers in. I was both excited and fearful of what it would look like when she combed it out.

Then came the dress which was very short. I would have loved to have seen Clare wear it. She had me put on white elbow length gloves. The shoes were T-strap with a 2 inch block heel and were surprisingly quite comfortable.

Clare feminizing Eric's face for the Halloween Party.

Then she went to work on my face. First she applied foundation and then powder. She used black eyeliner and mascara and applied it quite heavily. She used pink blush and bright red lipstick which she applied quite heavily.

"Now just sit here while I get dressed. Then I will comb out your hair and we will be ready to go."

I looked at the clock and was surprised to see that 3 hours had passed since we started. I sat there fidgeting, unable to get really comfortable in the tight corset. I was getting apprehensive about appearing in public dressed like a young lady. I tried to convince myself it was alright since it was Halloween, but was not doing a very good job of it,

After about 45 minutes, Clare come out looking like a gangster. She had applied fake hair to her face to give the appearance of a 5 0'clock shadow. With the toy machine gun she held in her hand, she looked very good, though it would be hard for her to pass as a man.

"Ok, Erica, lets comb out your hair and we can be on our way."

She removed the rollers and combed my hair out, giving me a part on the right side with waves down each side of my head. The hair just covered my ears. There was a single curl hanging down just above my left eye. For the first time I believed I could actually pass as a female.

She then put a band around my head with a pink feather sticking up in the back, and handed me a long cigarette holder with an unlit cigarette sticking out. She showed me how to hold it and wave it around for effect. Then she gave me a small purse and told me it everything I would need in it. She kissed me on the cheek and said we should be on our way.

Since she figured we would both want to drink, we took a taxi to the party. It was already in full swing when we got there. She saw Jenna, her closest friend and colleague, as soon as we walked in and led me to the table where she was sitting. She was with a big guy dressed as a confederate general. He had a long balck beard and when he stood up, towered over me, even in my 2 inch heels. Jenna was dressed as a southern belle from the same era. She introduced her friend as Thomas Jackson.

"Tonight, you can call me Stonewall," he said.

(For those not familiar with American History, Thomas "Stonewall" Jackson was a famous confederate general during the American civil war, who was accidentally killed by one of his own men.)

"I'm Eric Schiller" I responded and held out my hand to shake his.

"I think for tonight, you are Erica, Jenna said with a laugh."

Thomas took my hand in his, but instead of shaking it, he brought it to his lips and kissed it. I felt myself flush and my cock, which had been flaccid since Clare gave me the blowjob twitched. I wondered what was happening to me. My reaction to the female clothes and now to the attention Thomas was giving me was causing a strange reaction, one I preferred not to think about.

Clare got up to get us drinks. She brought back beers for Thomas and her, wine for Jenna and some kind of fruit punch for me. I protested that I too wanted a beer, but she told me that the punch was a more appropriate drink for a sweet girl like me. I finished it fairly quickly and Clare got me a second one.

I finished that one also, but before I could ask for a third, she took my hand and led me to the dance floor. The first few dances were fairly fast and there was little contact between us. I found the shoes easy to dance in and the dress gave me quite a bit of freedom to move. The band switched to a slow dance and Clare took me in her arms and led me around the floor. It was strange having her lead, but actually quite pleasant.

While we were dancing her phone rang. She answered it and I could tell by her expression and her end of the conversation she was not happy. It seems that one of her clients had gotten himself in a bit of trouble and she had to see about getting him out of it. We went to the table to get our coats and met with Jenna and Thomas there. It seems that Jenna had gotten the same message.

"Look, there is no reason for all of us to leave." Jenna said. "Why don't Clare and I go and take care of this mess, and we will be back here as soon as possible. What do you say?"

Clare and Thomas both seconded her suggestion and before I could respond, I found myself standing there with Thomas. Clare and Jenna had both taken off. Thomas offered to get us more drinks and I sat down at the table. The evening had been turning out better than I had expected, that is before Clare left. I felt a bit nervous being there with Thomas, the only person I knew at the party.

Thomas returned with the drinks and we sat and talked. He was an interesting person, and seemed to accept me, dressed as I was. We had a couple of more drinks and I was feeling light headed. He shocked me when he asked me to dance. If I had been sober, I would probably have refused, but the music was fast and I was getting a bit bored just sitting there, so, figuring I wouldn't actually have to tough him, I accepted his offer.

We danced a couple of fast dances before the music changed. I turned to leave the dance floor, but he grabbed my hand, spun me around to face him, pulled me close, and put his right arm around my waist so we could dance slowly together. Not wanting to make a scene, I put my left hand on his shoulder and allowed him to lead me. The band played several slow tunes and with each he pulled me closer till our bodies were touching. To my shock I felt his erection against me and I realized that I was turning him on. A greater shock was that I felt my own erection growing and realized there was no way he could miss it with our bodies pressed against each other.

By this time we were both thirsty and Thomas suggested we get a drink. I agreed, but before releasing me he leaned down and gave me a gentle kiss on the lips. It was not unpleasant and I found myself wanting more, despite the implications.

He got himself another beer and for me more of that fruit punch, which packed quite a punch (no pun intended). A short time later his phone rang. It was Jenna. She told him they would be quite awhile, the situation was complicated, and asked him if he would take me home. While they were talking, Clare called me and told me the same thing. She said she would be home as soon as possible, but suspected it would take some time to straighten everything out.

"Erica, shall we go?"

I had accepted being called Erica throughout the evening, so I merely nodded. He treated me like the girl I appeared to be, helping me with my coat, opening doors for me, and assisting my getting into the taxi. I remembered Clare's instructions about sitting on the seat and swinging my legs into the car while keeping them close together so as not to display my undies.

We arrived at Clare's and my apartment building and Thomas asked the cab driver to wait while he escorted me to our apartment. That was when I discovered I had no keys. I emptied my purse and was embarrassed to see a compact, lipstick, mascara and eyeliner, a feminine napkin, a tampon, and some coins. Thomas was a gentleman and did not laugh, but I felt my face turn red and then I panicked.

"What am I going to do? I can't just stand here waiting for Clare. It could be hours."

I was almost in tears.

"It's ok Erica. You will come with me to my house and wait there. I will text Clare and tell her what happened. It will be alright."

Then he took out a handkerchief and wiped a tear from my cheek. I felt so humiliated. I had taken on the persona of the girl I appeared to be. He took my hand and we walked to the elevator. He held it throughout the taxi ride and let go only to get his keys and unlock his front door.

He helped me off with my coat and motioned for me to have a seat while he got us something to drink. I sat down on his sofa and subconsciously crossed my legs at the knees, the way a woman would. Thomas returned with a glass of white wine for me and a beer for himself. He sat down next to me on the sofa. I took a large gulp of the wine hoping to calm myself.

"Are you alright Erica?"

"Yes, thank you. I'm normally not like this."

"Like what?"

"I don't usually act so helpless. These clothes have messed with my mind."

As I said it I realized how feminine I was acting, but I couldn't seem to help myself. It really was as if the clothes were forcing me to act like a girl.

Thomas took my glass from me and he put it on the table along with his beer. He moved closer to me and leaned over to kiss me. I realized what was coming, but made no move to stop him. He wrapped his arms around my waist and I put mine around his neck. His tongue snaked its way into my mouth and I eagerly sucked on it. His hand caressed my knee and gradually worked its way under my dress. He found the flesh between the top of my stocking and my panties and lingered there, slowly caressing me. I was as hard as I had ever been. He brushed his hand over my erection through my silky panties and I gasped. I really needed to cum.

He pulled his hand out from under my dress and put it under my knees. Then he easily lifted me and carried me into his bedroom. I hugged his neck and kissed him passionately. All thoughts of Clare were forgotten. I wanted Thomas and apparently he wanted me. He sat me on his bed and kneeled in front of me. He removed one shoe and then the other. He reached behind me and stood me up so he could slip off my dress. I stood there in my slip, my erection obvious.

I wrapped my arms around him and we kissed again. Then I unbuttoned his tunic and slipped off him. His chest was broad and covered with hair. He sat on the bed and I knelt in front of him to remove his shoes and socks. I unbuckled his belt and pants and he stood so I could slip them off him. He was wearing only his boxers, which tented out from his own erection.

"Take them off Erica," he said softly.

I hesitated for only a moment, but pulled his boxers down. His cock almost hit me in the face. It was enormous.

"Now feel it."

Tentatively I reached out my hand and touched it. It was warm and silky in my hand. I looked up at him and he was smiling at me. He nodded, as if to say I was doing ok. I had never touched another man's penis before, but I desperately wanted to play with his. I caressed him and he grew even larger. A bit of precum formed at the tip.

"Go on. Taste it Erica!"

I swallowed hard wondering if I was prepared to go further. Touching his cock was one thing, but sucking it was quite another. I looked up at him and he was smiling at me, patiently waiting for me to continue. I took a deep breath and tentatively licked the tip. Having swallowed my own semen I was prepared for the taste. It was not terribly different from that of mine.

I knew I had gone too far to stop now, so I took the head of his cock into my mouth and sucked on it. It seemed to get even harder. I caressed his balls with my hand and pulled his cock further into my mouth. It was so big I wasn't sure I could take the whole thing. He grabbed my head and slowly started fucking my face. I started to gag when it reached the back of my throat, but he pulled back. With each thrust he went a bit further and before long I was taking the whole thing. I felt him tense and I knew he was about to deposit his load in my mouth. Sure enough he came and despite my best efforts to swallow it all, some dripped out the sides of my mouth. When I felt him softening, he pulled out. With his finger he scooped up the cum that was on my chin and fed it to me. I licked it off his finger.

He lifted me up and lay me on the bed on my back. Then he crawled in next to me and leaned over to kiss me. His hand was soon under my slip, caressing my cock through my panties. He lifted my slip up to my waist and then pulled down my panties to free my cock and balls. He kissed me again, driving his tongue into my mouth and then moved down the bed. There he took my cock into his mouth. I felt a finger invade my ass and while he sucked on my cock, he finger fucked me. I could not believe how turned on I was. When I finally ejaculated, he swallowed all of my cum, not wasting a drop. Slowly he removed his finger from my ass.

I was totally spent, but when he got up on his knees, I could see he was hard again. He pulled my panties completely off me and lifted my legs, putting the undersides of my knees onto his shoulders, lifting my ass off the bed. He shoved a pillow under my ass.

"Uh..Thomas, I'm not sure about this."

"It will be alright Erica. I will be gentle."

A finger was one thing, but his cock was massive and I was not sure I could take it. He reached for some lube on the night table and reinserted his finger in my ass, lubing me up.

"No! Please Thomas. Don't," I pleaded.

"Erica" being entered for the first time by Thomas.

He continued to play with my ass using his finger. It felt really good and I stopped complaining. He lifted me more and I felt his cock at the entrance to my hole. He entered slowly, stopping frequently to see if I was ok. It was uncomfortable and a bit painful, but his gentleness convinced me to allow him to proceed. Finally he was all in. To my shock, I was hard again. He leaned over and kissed me. Then began fucking me slowly. It was like nothing I ever felt before, and it felt good. I was playing at being his girl and I was enjoying it. His hand caressed my cock. I could feel my own tension building and knew I wouldn't last long. He seemed to be getting bigger and I felt him start to cum. He filled me up with his warm juices and then I too came, getting us both wet with my cum. When he was spent he collapsed on top of me. I slipped my legs off his shoulders and wrapped them around him. We lay there in that position for awhile, hugging and kissing each other.

Finally he rolled off me onto his back. He turned me on my side, facing away from him. He wrapped his arms around me and before long I realized he was asleep.

The next thing I was aware of was the sun streaming into the room, and I had to take a wicked piss. Thomas was nowhere to be seen. I went to the bathroom, lifted my slip, pulled own my panties and sat. I didn't want to think about what was dripping out of my ass. I wiped myself the best I could and went back to the bedroom. Clare was sitting there on the bed.

"Good morning Erica."

"Clare! What are you doing here?"

"It looks like you had a good time last night," she said, ignoring my question.

She was staring at the cum stains on my slip.

"Clare, I..I can explain."

"No need. I can guess what went on here last night.

"Sit down Eric. We need to talk!"

I did not like the sound of that. I wondered if she was going to break up with me and if it had something to do with my obvious actions the previous night. She patted the bed next to her and I sat down fearing the worst.

"Eric. I love you. I really do."

"But" I said, fearing the worst.

I could hear the apprehension in my voice.

"But, it is not working for me the way things are."

"Because of last night? I can explain."

"It has nothing to do with last night. I haven't been totally honest with you Eric. Last night was a test for you. A test on which you got an A+.

"What do you mean?"

"There was no client to see. The message I got was from Jenna telling me it was time to leave. We planned on leaving you alone with Thomas and I purposely did not put your keys in your purse. Jenna and I were in a motel together. As you well know I am bisexual. Jenna and I have been lovers since college, and I have continued seeing her throughout our relationship."

"I..I think I can live with that."

"Wait. There is more. I have told you that I can't orgasm from sexual intercourse."

I nodded.

"The truth is, I can't cum from sexual intercourse with you. You are too small, and quite frankly, not nearly aggressive enough in bed."

She held up her hand as I tried to respond.

"I have also been having sex with Thomas. He gives me the best orgasms I have ever had with a man"

I was stunned. I could feel tears welling up in my eyes as I realized I was losing Clare.

"I want you in my life, Eric" she continued. "But it would have to be different. I am moving into this house with Jenna and Thomas. We want you to move here with us, and have an open sexual relationship."

There was a thread of hope there and I was determined to grab it and hold on.

"I think I can do that."

"You haven't heard all the conditions."

"What conditions?"

"Thomas, Jenna, and I all have large incomes, dwarfing what you were making before your layoff. We want you to be our maid, take care of the house, the cooking, laundry, etc."

"M..m..maid?"

"Yes. You will dress as a female at all times. You will be available to provide oral sex to Jenna and me, and to service Thomas orally and anally when he so desires. In return, we will take care of you, give you a salary, and provide all your expenses. You will not have intercourse with me, nor will you have it with Jenna, unless she desires it."

"A maid?"

""Yes, a maid. You will be a servant, though not a slave. You will be paid a living wage and can opt out at any time."

"I have given 30 days notice on my apartment. You are welcome to stay there until that time is up should you decide not to take us up on our offer. I know it is a lot to think about, but we do need a decision. We have another candidate for the position should you decide to turn us down."

I was stunned. I tried to say something, but no words came to mind. I didn't want to lose Clare, but did I want to be a maid and service them all sexually, with no hope of intercourse?

"Let me help you out of those clothes and you can shower. I'll get clothes that I brought for you from the car."

She leaned over and kissed me, with passion.

"I do hope you will choose to move in with us, Eric. I really do love you."

Then she helped me remove my slip and unlaced mycorset. It felt good to get out of it. She unhooked my bra and I slipped my arms from it. Clare left the bedroom and I removed my now shredded stockings and panties, which were badly soiled with my cum. I was moving in slow motion, trying to digest everything she said to me.

When I came out of the shower I had a towel wrapped around my waist. I immediately saw a pile of clothes on the bed with my jeans, a pair of boxers, my favorite tee shirt, socks, and trainers. There was a piece of paper on top. As I reached for the paper I noticed another pile of clothes on the other side of the bed. Curious I went to examine it. It contained a denim mini skirt, a pink tee shirt with red hearts on it, a pair of white silky panties and a matching bra. There was also an unopened package of pantyhose and a pair of red sandals with a modest heel.

I was confused. Hoping it would provide an answer I picked up the paper, unfolded it, and read it.

By choosing your old clothes, you are saying good bye. By choosing the new clothes you are saying hello to a new life.

Love you,

Clare