My Summer of Sissification

I met Zooey on a flight to Chicago. We sat together, isle and middle seat, and both drank cans of Budweiser that we poured into plastic airline cups. Zooey had short curly blond hair, wore a blue sweater cape and kept a pair of fluffy white mittens on her tray table with her beer. The few times she spoke she licked her lips, wetting them. She told me she grew up in Des Moines and that she'd moved to New York after getting an associate degree in computer science from a community college. She coded for a local bank. She was visiting her sister in Chicago.

She had wet blue eyes. Whenever our eyes met she looked as if ready to crumple into sobs.

I asked her if she was sad. She shook her head no.

We took a cab to my hotel downtown. Room service brought us a six pack of Budweiser. She sat on the bed turning the pages of Cosmopolitan after she opened a can of beer. I unpacked my shave kit, turned up the heat and took off my shirt.

When I laid down on the bed she reached for me. We kissed.

Her kiss was troubled, hurried, lacking. She undid my pants and pushed them down enough to reach inside my jockey shorts and pull me out.

"Fuck me," she said. Her words had an unfounded directness yet her voice quivered.

"What?" I asked.

"Fuck me," she said. "Take off your clothes."

But again, there was something awkward or hollow, in her request. She seemed a shy girl who'd summoned a new voice that was fragile and forced but necessary.

She sat up and pulled one of her breasts from the cup of her bra.

"How this?" she asked. She stood up straight.

Her large round pale breast had a small areola and a long hard nipple.

I didn't respond but felt unease. Her lack of surety belied something she wanted. She was being honest. I felt her desire. It was there beneath her reddening cheeks. She wanted something.

She got off the bed and stood up. I could tell she'd been struck by another idea. She opened her purse and took out a small makeup bag.

"Come here," she said, extending her hand. She grasped my wrist, squeezed, and started to tug me off of the bed towards the white tiled bathroom.

"What for?" I resisted and fell back.

"Just come on," she said. Her cheeks flushed again, tears pooled in the corners of her eyes. She dropped her extended hand, leaned over me and whispered in my ear that I needed to take off all my clothes.

I undressed but my penis stayed soft. I gave her my hand and she hauled me up.

"Stand here," she said, positioning me in the center of the bathroom mirror. She'd left her breast out.

"Put your hands behind your back."

She took my chin in her hand and opened a tube of lipstick with the other.

"Hold still."

She brought the lipstick to my lips and started on my upper lip before I stepped back.

"What are you doing?"

"Come on," she said. She backed away, uneasy. "I've always wanted to do this"

Amused, with a touch of pity for her, I thought, why resist? She coated my lips in red. Then she did hers.

"We're twins," she giggled.

She giggled a lot, her eyes watering with joy. We stood looking in the mirror together. My penis hung unresponsive. When she smiled the tears were gone, she nudged my arm with her elbow, grinning a show of straight bright white teeth. Her blond curly hair fell all over her face. She was beautiful.

I felt clownish in the lipstick. Then I didn't.

"You're beautiful," she said in a calm sure voice.

"I know," I said smacking my lips together, pretending, doing what I thought I'd seen women do.

A kind of peace arose. Maybe love. It reminded me of the way I felt when I'd had an honest conversation, got something off my chest someone understood.

Zooey held her index finger up in the air while looking at me in the mirror.

"There's something else I want. Take your thing and push it between your legs."

"What?"

"Push it down between your legs. Like this." She put her hand between her legs demonstrating that I should press my cock and balls back through my legs. I did this and held it there.

"Good. Now bring your leg over top the other."

I told her I didn't understand so she got down on her knees. She grabbed hold of me with her right hand and yanked my shaft and balls back between my legs and with her left hand pulled my right leg and foot out and over my left foot so that when I looked down between my legs in the mirror, my penis had disappeared. I looked like I had a woman's black pubis. No cock.

Zooey stood up at my side. We watched ourselves in the mirror.

"I like that," she said. She raised her chin up and pointed into the air. She was inebriated, flush, beaming as if we were children. We were.

She leaned on me, tilted her head up for a kiss and we kissed. Her anxiousness was gone.

I started to uncross my legs. I had turned towards her. I was stiff. The friction of my shaft, pulled tight, and pressed against the top of my left thigh felt good.

"No no," she said. "Stay the way I put you."

She turned me to the mirror.

"It feels good doesn't it? Think you could make yourself cum?

"Maybe," I said. "It feels good. Tight but good. It's weird."

"Try," she said. "Keep going."

She watched me closely, twisting her head as if she needed to stretch. She reached inside her jeans while she watched me, worked her hand down between her legs. Tears rolled down her cheeks. Her breathing quickened. She grew more red faced.

"I want you to cum,"she said. "Move your hips up and down like a girl."

The feeling was a pleasant kind of friction that could get me off. In just a few minutes it did. I came.

When I finished I started to uncross my legs but again she stopped me and got down on her knees. I felt her run her finger along my upper calf and thigh. She stood with a finger full of my thick white semen.

"Open your mouth," she said. She pushed her finger in and smiling, told me to lick it off.

She didn't stay long.

"Here's my card." she said. We hugged and said goodbye.

I called her the next night after I'd had several tequilas.

"What was that all about last night?" I asked.

"Nothing," she said.

There was a lot of silence. I struggled to think of something to say.

I said something like it was fun and she said yes and then there was another minute of silence. I'm not usually tongued tied except around beautiful girls and she was not only beautiful but apparently very kinky. After another minute of silence I said that I would call her when I get back to New York.

"Okay, bye," she said.

We met at a dark bar in Brooklyn. I carried the conversation but had prepared a few questions anticipating the silence. Still it didn't go well.

"What kind of movies do you like?"

"I don't know. I don't watch a lot of movies."

"How do you like your work?"

"It's okay."

"What interest you besides putting lipstick on men?" I said.

"That's the first time," she said.

"Do you think I'm pretty?"

"Yes," I said. "I think you're the prettiest woman I've ever dated."

"We're not dating," she said.

"No. No," I agreed. "But I wouldn't be sitting here if I didn't think that."

"What?"

"That you are beautiful," I said.

She made a blubbering sound with her lips, the kind of farting sound kids make. She ran her finger around the opening of her Bud bottle.

"I want to take you to a salon, she said.

"For what?"

"To have your toenails done," she said.

"I don't think so."

"It will feel good," she said.

She lifted her chin high in the air then rolled her face down towards me so that her wet blue eyes drilled into mine.

"It will feel better than you think and I'd like to watch the pedicurist file your nails and then you can pick a polish color," she said.

"No, no I'm not going to get my toenails painted." I was firm.

"Lots of men do. I think you'll like it."

She'd raised her chin and shook her head no. Behind her a row of yellow lights lit the labels on the bottles of scotch. A mirror rose up to the ceiling. I watched the back of Zooey's head for a moment. She opened her mouth as if to laugh then closed it and smiled tight lipped with again. She had tears in her eyes.

I don't know why I agreed. Nails by Doris was in a strip mall off a main intersection at Livingston Avenue. The place was busy and bright, over lit, and smelled like chlorine and model airplane glue. I felt welcomed.

A robust overworked looking stylist appeared behind the counter

"First time here?"

"Yes."

"Okay have a seat," she said.

It didn't occur to me that I was out of place. I sat in a red cushioned metal chair next to Zooey who thumbed through a ragged copy of Glamor magazine.

At the station my pants were rolled up. The pedicurist took both my ankles in one hand, lifted them as if I were an animal at the vet, scooted a small tub of water beneath them and then lowered my feet into the tub. Zooey asked "Does it feel good?"

"Yes," I said.

For a few minutes I had a very pleasant feeling- like I was above everyone.

"I'm not going to have my fingernails done," I said.

Zooey nodded and laughed with her mouth wide opened bobbing her head up and down.

After the bath, the clipping, the filing, and my toenails were painted, the stylist led me to a station where I put my feel in a dryer. When she was done I admired them. Nothing extraordinary, but I knew I'd hide my toenails from everyone except Zooey.

We stood outside the salon. Tiny flurries of snow fell sporadically in large irregular patterns. Zooey hugged me and said she had to get home because her boyfriend was coming over for dinner.

"When will I see you again?" I asked.

She turned and smiled at me as she ducked into her light green Honda Accord and drove off.

I called her that night after I'd taken a long, unusual, three hour nap. I thought the spa chemicals might have induced sleepiness. Maybe it was Zooey. I laid down with the hope that I'd have a dream about her.

She didn't answer my call. I started thinking about her boyfriend and what he'd think about me and what Zooey and I were doing. I wondered if she had told him.

The next day on my fifth attempt Zooey answered. She said hello with a gusto that suggested she'd been waiting for my call.

"Can you come over for dinner tonight? You can meet my roommate," she said.

I said that I couldn't because I had plans and she hung up.

I called her back an hour later and said I didn't have plans. She told me how to get through the gate. Zooey lived on the third floor in a two bedroom condo above a big courtyard swimming pool.

Liz, her roommate was the same height as Zooey. She had sandy blond hair, a circumspect face, and big green eyes.

"Nice to meet you Nicole," she said extending her hand.

"My name is Nick," I said.

"Yes. But when you're here we'll call you Nicole," Liz said stepping back.

"Well my name is Nick." I insisted but not by much.

Liz shook her head no. We all stood in the very tiny entranceway, on white linoleum, between their kitchen and the light brown carpeted living room.

"When you're here Nicole you'll be Nicole."

"It's not nice to call someone by a different name without their permission."

"We know that," Liz said, "but you'll get used to Nicole. It's like exercise. At first you resist and then you realize it's good for you."

"It's not good for me. I'm Nick."

"It's good for us, so it's Nicole," she said. "Why don't you fix us some drinks We both like vodka, tonic and lime. You'll find everything in the refrigerator, glasses in the sink."

Zooey cupped her hands together, put them to Liz's ear like first graders do and whispered. Liz told me to hold off on the vodka tonics and gestured for me to follow them to the back bedroom.

Zooey opened the top drawer of a blond wood chest of drawers. She pulled out a pair of white panties and held them up opened hips-width between her thumbs and forefinger.

"We want you to wear these tonight," Liz said. "Put them on Nicole."

"Please call me Nick."

Liz stood back. Her face stiffened. "I don't want to sound mean but If you don't like Nicole you're welcome to leave. The same goes for putting on the panties."

"I don't want to leave," I said.

She nodded at the panties.

The fact was that both Zooey and Liz were young beautiful women, both in their mid twenties, likely at the peak of their beauty and reproductive desires. They both had good sized firm full breasts and round bottoms beneath there curved baby bearing hips. There's nothing I loved more than a beautiful round female bottom. So when it came down to it I didn't particularly care if they called me names or asked me to do things I didn't really want to do.

I undid my belt and pulled my jeans and underwear off. "Take off your socks off too. I want to see your red toenails," Liz said.

I stood half naked in my yellow polo golf shirt. My penis retracted, very small..

"Doesn't look like he's a true sissy," Liz said. "He'd be hard if he was."

I put the panties on. Liz said okay now you can make us drinks.

When the doorbell rang Liz told me to get up and answer it.

"I can't," I said.

"Get the door Nicole. It's the pizza," Liz said.

I hid behind the door as I opened it. As I took the pizza in one hand Liz pulled the door open and handed the delivery guy cash. I hurried into the kitchen.

That evening after pizza and a Batman movie the girls asked me to follow them into the bathroom. Liz pulled my panties down to my ankles and told Zooey to color my lips with a lipstick that matched my toenails.

"Could you show me one of your breasts," I asked, looking at Zooey.

"No," she said. Her face grew bright red. She unzipped a small plastic bag with pictures of elephants on it and rifled through it.

Liz said, "Nicole, look, how's this?"

She turned around so her butt was facing the bathroom mirror and then yanked down her leggings and underpants revealing her perfectly round white bottom. She let me gaze at it before pulling them back up. My penis thickened. Liz nodded at Zooey to put on the lipstick.

After the lipstick, Liz told me to put my penis between my legs like Zooey taught me do in Chicago. After I did it. Both girls squatted behind me. I ejaculated watching myself in the mirror, watching the small patch of black pubic hair that looked like the public hair above a woman's vagina. I thought that maybe I was both a man and a woman. I came quickly. I heard Liz ask Zooey, if she had me lick it up and she said yes. I felt their fingers running up and over my calf and thigh collecting my semen. They both put their gooey fingers in my mouth.

I floated home. I couldn't sleep. I felt transfixed and yet lost, disconnected.

I was in graduate school getting a degree in geology and my studies were suffering. I couldn't stop thinking about them. I was entranced they were beautiful.

I didn't hear from Zooey for a week. I didn't call. I wanted to be called. Several times I told myself I'd had enough. It was behind me. They must not love me. But once after showering I stood in front of the mirror and put my penis between my legs, rubbed, and came while admiring how the pose made my hips seem womanly.

That night I called Zooey.

"Why haven't you called? Have you stopped loving us?" She said.

"No no," I said. "I want to see you. I did what you made me do in Chicago this morning."

"Oh, that's fine," she said.

"Why don't you meet us for lunch on Saturday downtown at Arias," she said.

"Okay. What time?"

"At noon," she said.

"That's fine," I said.

"Wear flip flops so we can see your pretty toes," she laughed.

"I could but I don't own any flip flops," I said. There was a long pause and I thought Zooey might have hung up.

"You can get a pair at the dollar store," she said.

At the restaurant the three of us sat around a four top.

Liz began talking. She looked me in the eyes. "People don't care as much as you think."

"But they do. You're from Iowa," I said. "I don't believe there are a lot of men farming corn in Iowa with painted toenails"

"It's not what you think. Yes they'd laugh and call you a sissy. Then they could care less," she said.

Liz went on to say there were a small group of people who needed to diss people unlike them. The dissing helps them feel righteous and strong.

We sat silent eating our salads. Zooey and Liz both wore shorts and thin tee shirts with no bras. After a while of no conversation I went to the restroom and Zooey followed.

"In here," she waved, gesturing for me to enter the ladies room with her. She locked the door. She took out her make up bag and put lipstick on my lips, blush on my cheeks and made me close my eyes to put on eye shadow. I looked flush. My hair was pretty long then. She pulled it back tightly and put a fitted knit head wrap on. From her bag she took out a pair of flip flops and told me to give her my shoes and socks which I did.

She unlocked the door and pushed me out. "Go go," she said. She grinned. Her eyes watered. Stepping through that door dressed as a woman was unbelievable. I broke free of something. For the first ten steps back to the table I felt an incredible peace as if I was in the hands of a living God.

That evening Liz called me and we talked for over two hours. She told me that both Zooey and herself had fallen in love with me and wanted me to come stay with them a few nights a week during the summer. I said yes immediately.

She told me they already been shopping for clothes and picked out several underthings and girl clothes that they couldn't wait to have me wear for them. One night, at the mall I went through the woman's section at H&M trying to imagine what would make Zooey and Liz smile. I bought a few things.

At the university, which was close to their apartment, I attended classes on Thursday and Friday afternoons so I agreed I'd stay on those nights. They set up a little cot for me to sleep on in Zooey's room.

I wore lacy white panties, dresses that were pink, navy, and various pale shades. My legs and chest were shaved smooth. They had me wear nylons, bobbie socks, a red pleated plaid school skirt, and matching white blouse. It was all lots of fun.

Once a week we'd all go out to a restaurant together with me dressed as a woman. There were a few strange looks and one guy walked by our table and said, while passing, that this is a family restaurant not a place for perverts.

Towards the end of the summer, on Friday night a large man knocked on the door of their apartment. I was in a light blue night gown and matching panties.

You must be Nicole the man said. I've heard a lot about you from Zooey. I'm Fred, her fiancé.

Zooey slipped past me snd threw her arms around Fred's neck and lifted herself up into her arms as they kissed.

"I'm glad you finally met," she said.

I went into my room and lay on my small cot to go to sleep. Fred and Zooey came in and ignored me.

"Would you like me to go sleep on the sofa?"I asked.

"No," I heard Zooey say.

She and Fred undressed and laid down together and began kissing. I watched through half closed eyes. She laid on her back and he laid on top of her pinning her to the bed. He thrust in deep high arcs such that I could hear their pelvises crashing against one another as if the main thing at the heart of the relationship between men and women was war. Fred slowed his thrusts when Liz walked in.

She sat at the side of my cot and brought her face down by my head. She rubbed my penis through my panties.

"You're so hard. Did you know Zooey is getting married?," she whispered.

"No."

"Fred is from the midwest too, not far from Iowa. He's Siouan. They met at the boot shop he owns. They hardly speak. But she loves him," Liz said.

"I love her too," I said.

"I know you do. She loves you too but not like she loves Fred. She loves Fred because he's a man. You're not really a man. You're something else, maybe something in between," she said.