The Married Men of Summer Pt. 01

*Stories from the real world 2.5

This story is slightly, slightly, very slightly autobiographical. Ha...

***

Between the beginning of summer 1987 and the end of spring 1988, life was, well interesting...

"Wait." Big Al was interrogating me, like usual. You have been with three guys and they were all married? You are such a slut."

"All three were accidents, I didn't plan on any of them," I explained, I was a nice girl.

"Doesn't matter. So I'm guessing you have a type, it's a wide net, but still a net."

Big Al was my friend, Alyssa Cafferty, she came from a big Irish family. Five siblings, two parents, and three grandparents lived in her house. They lived above me, all eleven of them, they woke me up and kept me awake. I didn't mind, I didn't sleep too much, I slept in pantyhose and a teddie, I was usually excited. I turned twenty-three in January, Big Al was a year older, and we were suddenly inseparable. She also wasn't that 'Big,' maybe 5'6" I was 5'8". When we wore six-inch heels we were still close to the same size. Oh, and it was Big Al's bra size that got her that great nickname. She was a C in grammar school and a D in high school, she was bigger than that now and she was very popular in the neighborhood.

"Hey Big Al, shake!" The men would yell when we walked the Avenue.

"In your dreams!" She would yell back, sometimes giving them the finger. She was real good at that.

I moved to Bay Ridge, Brooklyn a couple of months before, I wanted to get dressed up more, I needed to grow up and get out of my parent's basement. I moved, and so did they. They were now in Connecticut, far enough away that I didn't have to visit too often. I lived on the bottom floor of Al's house, I shared the floor with four other people, we shared a kitchen. To think I moved because I wanted some privacy, now I had none.

"Can we talk about something else?" I was begging Big Al, she loved to ask about my insignificant love life, my slightly slutty past, she thought it was hysterical, salacious, and just plain crazy. "Sometimes I wish you never found my pumps."

"I can't believe you were keeping that a secret, that is literally the only interesting thing about you, haha."

A bunch of months before, Al was snooping, she was in my closet. It was big, it was almost a room, I was grateful to have it in my apartment. She found a shopping bag full of heels. She questioned me and when I didn't give her the correct answer she threw them at me, one by one. I had to succumb, I had to tell her about me. It was a secret to almost everyone, and now I had to tell my landlord's daughter I was a crossdresser, maybe even transgender, but definitely a crossdresser.

I had more heels than outfits, they were my favorite. Stockings and heels were all I really needed, but the rest was nice I loved to look, smell and feel like a woman. I loved to smile in my mirror.

"So I love heels, pantyhose and I have a thing for mascara. No big deal. Right?" I asked her. It's not an easy thing telling a beautiful woman that you want to wear women's clothes. You want to wear her clothes. It's even harder telling a beautiful woman about your sex life, with men.

"I completely understand, there is nothing like a short skirt, a tight sweater, higher than high heels, and mascara, come on I love that. You are preaching to the choir sister." Actually, it turned out it was pretty easy telling a beautiful woman about myself. That first night she went through all the female clothes I had, all the lingerie and heels. She picked through all my makeup, sundries, and accessories. She threw things out, she took notes. She said she was going to help me, she was going to be my mentor, my older slutty sister. She made me try everything on in front of her, she rated my catwalk technique, my strut, even the way I sat and crossed my legs. She called me a flirt.

Alyssa taught me three very important things, One; How to check my nails to make sure people were watching me. Two; How to eat off of a fork so I don't mess up my lipstick. and Three; How to meet and introduce myself to others.

The next night she introduced me to a woman. I was Samuel in my male mode.

"How do we know?" Al asked, "Do you only like men?"

"I don't know, maybe. Well, when I am dressed up..."

"Well, then this is a test." And she introduced me to a very short woman, she was maybe five foot, maybe, with a Dorothy Hamill haircut. "Donna, this is Samuel."

I shook her hand, she was happy to be out of the house, the thing was... my femme name was Donna, it had been that for years. I think Big Al did that on purpose, she was trying to confuse me and it was working. The relationship with the 'Tiny Donna' didn't last long, it is only rememberable because it prompted me to change my name to Sabrina.

*

But this was still the summer of '88, I was still Donna. That was the summer that Big Al decided I should also continue my experimentation with men.

"Oh, my god, me and you in heels, big grabbable breasts, we are going to be so busy. I finally have someone to whore around with, hah,"

So that summer I had two jobs, I kind of dated a woman, I lost thirteen pounds and I had relationships with five men, married men. It turns out that was Alyssa's ideal summer.

***

Married Man Number 1

"Don't be mad." I heard Big All call from the small living room, I couldn't really hear her I was drying my long strawberry blonde hair. We were getting ready to go out.

"What?"

"I told the others in this apartment that a woman is living here now. So if they see you in a bra don't worry about it."

"What? Why?"

"Why? What do you think? First of all, you are so hot and I don't want you bouncing back and forth between genders. You are sticking to one, and that's female." She went back to making drinks. Her hair was already dry, it was perfect and dark brown and landed in the middle of her back.

"But what about 'Tiny Donna?' She's going to wonder isn't she?" I was getting nervous, Al made me ask her out and we had about three dates already. They were all terrible, she was always a little on edge, she hated her parents, her job, the guys at the pizza place, even her cat. And she was never happy with whatever she wore, it was either too big, too tight, or clashed with somebody else. I realized right away I was a better woman than her. I was nicer, I smelled fresher, I was a better dresser and I put out, unlike her.

Once I would get home from one of our dates I would change into lingerie, put on a little makeup, and read my magazines. I would make believe I had a date with a man instead, I would make believe he gave me an incredible orgasm. I would make believe I was talking to him on the phone.

'Hi, I had such a wonderful time tonight, I'm thinking about you. What? Okay, I will play with myself if you will.' And I would giggle. I would kick off my heels and get under the covers.

I was startled, Big Al was talking to me in the mirror, she was behind me, she was rattling the ice in our two glasses. "I told Tiny you were working on a cruise ship for the rest of the summer, told her you were a maid, ha. You got time, you can break up with her in September." She laughed and handed me a rum and Diet Coke. "Or we could stop by her house tonight. Freak 'er out a little."

"Ugh! And what about work?" Both of us worked at a huge bank in Manhattan, sixteen stops away on the subway.

"Will you stop asking questions, what are you so worried about."

*

It was a quiet, warm Friday night and I was so nervous, Big Al was making me wear jeans. Jeans!

"Come on, you look great in jeans." She said and then slapped my ass.

Very tight jeans, very blue. Underneath she made me wear panties, Sheer Energy pantyhose, and these weird-looking foam things to make my butt and hips look bigger, and they did. My ass was now nice and round. I had on her strapless bra, filled with these D-cup mastectomy pads. Al got them from her friend who worked in a store that sold scrubs and nurse's uniforms. They looked and felt like real breasts, but they weren't as nice as Alyssa's. I had on a long-sleeved billowy white top, sleeves went down to my palms. The top showed off my shoulders, the bottom showed off my belly. Al said those were my most feminine features. I then slipped on a pair of five-inch open-toed black pumps, showing off my red nails and reinforced toes.

She was rushing me as I curled my hair, it went just past my shoulders. I put on big clip-on hoop earrings and then sprayed on some Avon perfume. Al then painted my nails, they were long, press-ons, and were held on with super glue. I had no problem at all with them, I didn't know how I was going to take them off.

Alyssa was all in white. White jeans, white top, and white heels, she looked like an angel. She had her long nails painted coral, she was too lazy to paint them white. We then took pictures, lots of them, I had a Kodak Instamatic, it used 126-type Pak film. It took over two weeks to develop. I couldn't wait to get back the prints, I was starting a scrapbook. It was mostly of my legs and Big Al's breasts.

"Come on, pocketbooks, let's go." And we went out the front door, the new female in this apartment was settling in for the summer. She kept her head down, the hair in her face, she was now making sure she had everything she needed in her bag.

Allyssa had it all planned out. We were going to a social club, it was run by a huge Italian man named Julie. It was right around the corner from the house. Julie saw us and beckoned us in, we followed. We went through the front room, set up like an office, couple of chairs, desks, bunch of phones. Next, we went through some kind of make-shift warehouse, full of boxes, hand trucks, and shelves and shelves of liquor bottles and cases of Italian wine. We ended up in a room full of tables and chairs, with three televisions on the walls. There was a full bar in the back and a man with a hat playing solitaire behind it.

"Julie, what's this?"

"This is your present, well only one is your present the other is a gift to myself."

He smiled at us, it made me nervous. He gazed from my heels and then back up to my eyes, he took a long pause at my breasts. Julie helped us both onto the bar, he lifted us around the waist. We sat, we crossed our legs, and Julie admired our footwear.

They then gave us little shot glasses filled with a toxic green liquid. "Always start with Kamikazes." He held up his drink, we did the same and shot it back.

Sour, lots of lime, I liked it a lot. "Mmm, I love this," I said in my sweet little girl voice.

"Ah, this one's mine." And the man took my empty glass and gave me another one.

Julie helped Big Al off the bar and they backtracked into the warehouse. She winked before the door closed and she was gone, leaving me alone with the tall older man. He took off his hat.

"Cheers." And we clinked glasses. We drank, he watched me, he had a smile on his face. "I'm Sal, Sally Moon, heh, welcome to the club."

I was nervous, I needed another drink. "I'm, um, Donna, I'm from the neighborhood."

"Of course you are." He then uncrossed and opened my legs, he moved between them. He rubbed my thighs, enjoying the jeans. Soon his belly was pressing against my flat crotch. He put his face into my breasts. I felt him separate them with his nose, he started kissing them, my top was starting to get lower, the top of my bra was showing and I tried to fix it, but he took my hand. He looked at my long nails and he kissed my fingers, he then put my middle finger into his mouth. His other hand continued to rub my thighs.

"Can I have one more, please?" I held up the little glass, I was nervous, he was feeling up the lower half of my body a little too thoroughly, he was making me excited.

"Ha, sure sugar." He went behind the bar, he made two more drinks and handed me one, I turned my head sideways and smiled at him, he was quite good-looking, probably in his forties. He had big arms, and wide shoulders, he was all man. He was the complete opposite of me. I just hoped he didn't investigate my breasts any further. He was a little higher behind the bar and he started to investigate my breasts.

"Mmm," He moaned into my back, on my neck, he started to kiss my hair as his fingers searched for my non-existent nipples. I downed the next shot and then tried to spin around, my long legs on the bar, knocking over a napkin holder, a glass of stirrers, and even his shot glass with my heels. He laughed as I ended up in front of him.

"I'm sorry, I'm so clumsy."

He put his face right in front of me, he looked into my eyes. "You might be clumsy, but you are too pretty for me to notice anything else." He laughed and then he kissed me, I think he tasted like lime. Of course, he cupped my breasts. I was nervous that they were so popular tonight.

"Mmm," I hummed, I put my hands around his neck as I pulled him into me. He had his tongue in my mouth as I started to play with his short hair. I felt my breasts now rubbing against his chest, his hands finally on my back. Every time I thought he was going to remove my bra I readjusted and kissed a different part of his body, his cheek, his chin, his shoulder. I teased him with my hair on his face.

I was enjoying myself making out with a man. I have always loved doing this, once I am wearing mascara, long nails, all I think about is men, pleasing them, hopefully playing with their cocks.

I whispered into his ear, "Maybe we could trade positions." I giggled, I wanted him to think I was cute, think I was a sexually active woman.

He smiled, and he kissed me again. "Sure." He helped me off of the bar. He first grabbed my ass as I stood next to him, he let me rub against him. I put my arms around his neck and we kissed again. I was starting to get hard, I was getting into it, getting over-excited. I was tucked tight in little panties, a pair of pantyhose, and tight jeans, Big Al knew what she was doing when she dressed me.

He then hopped up on the bar and I moved between his legs. I rubbed my breasts onto his thighs, I pushed my face into his crotch. He was hard, his cock was making its way down his pants leg. I opened his zipper as he moved up just a little, just enough to pull down his jeans. I played with him through the cotton of his white briefs. I watched his face, his smile as I rubbed his cock, teased him, then maneuvered his dick through the pee hole. He was so hard, I was making him excited, I felt I was going to cum so I attacked his cock. I slid him into my mouth causing pressure with my red lips. His cock felt so good, I was so excited, I couldn't believe it, I started to cum.

I pulled my lips off his dick, "Oh my god baby," I started to moan, my lower half was thrusting against the shelves of the bar, I held on to his cock. "Your cock is so hard, your making me cum." I heard him laugh as his hands went into my hair, I went back down on his rock-hard dick. I felt my panties get wet. I heard a noise.

"Ay, Sally, um, sorry."

I stopped sucking, I looked behind him, there were two men.

"Hey guys, sit down she's almost done." He said to them, he guided me back onto his manhood. I was now nervous again, all the alcohol had magically worn off. I started sucking, sneaking a peek at the two men at a table behind him. One of them winked at me when I checked to see if they were paying attention. They were.

"You are such a good cock sucker sugar." He was rubbing my cheek he was watching me on his cock. I smiled, I felt my long lashes flutter, I loved him complimenting me.

Soon he put his hands on the top of my head, he was taking control, he was grabbing my hair, he started pushing me on his dick. He was so hard, he was so big, I couldn't take too much inside of me. He started leaning back, he started stretching his legs, he was moaning. I put one hand around his hard cock and the other holding onto his thigh, trying to stay still, hoping for a little support while I balanced on my heels, as he thrust his cock in and out of my mouth. He pumped and pumped, I tried not to gag. I was loving it, I was getting excited again. All of a sudden he let go of my hair and I pulled off of his cock with a loud breath, he started to shoot his load, he started to moan even louder. He came on my face, I opened my mouth and he came inside of me. He milked his dick until he was done cumming, directly onto my tongue. I took him back into my mouth and cleaned him off, swallowed every bit I could find.

"That was incredible, baby." He said as I looked back up at him, I slowly let him through my lips the last time. I got to the head and I sucked a little more, he came out of me with a pop and I kissed the head.

"You taste so good," I told him, I smiled at him. I probably looked a mess, my lipstick was now all over his cock.

I stood back and he kissed my cheek, he jumped down and fixed his pants. "Drinks on me fellows, I just got the best birthday blowjob I have ever gotten in my life." He laughed, he kissed my cheek, he made more kamikazes and gave one to me and I brought the other two out to the men. They watched me as I got closer in my high pumps. I let the two of them rub my ass, I felt a little too confident, I totally felt like a girl.

Sally yelled to me as I picked up my bag, and got ready to walk through the door, out of his life. "Hey Donna, when do I get to see you again?"

I smiled, I flicked my hair behind my shoulder. I took my little mirror out and fixed my lips. I checked my nails. I would let him wait for my answer. I smiled at my reflection, I wanted the men to watch me. I finally looked up at him, behind the bar, probably another hard-on in his pants.

"Next year, of course, happy birthday." I gave them a nice girlie wave, a wink, and walked through the little warehouse, I came out into the office.

Big Al was at the desk with Julie playing cards. "Rummy, ha." She put her cards on the desk, she looked back at me, "Wow, what took you so long?"

"Yeah, we are on our third hand." Julie laughed, "If I knew you were so thorough I would've taken you instead." He laughed again and shook his head. Big Al got up, brushed her breasts off, and grabbed her bag.

"Hold on, I got somethin' for ya. Don't tell anyone." Julie reached under the desk and gave us two paper bags, both big, both rolled up at the top. "Here ya go, a present from me."

We each kissed him on the cheek and we left the club. There were two women outside smoking, watching us leave, they didn't seem happy to see us. Big Al cocked her head back towards them, "Those are the wives, ha."

"No."

"Yes, haha. That was the deal. The wives had to know."

We went to the little bar a couple of blocks away, we sat in the corner, we wanted to see what Julie gave us. "I hope it's something to make those kamikazes, god those were so good." I looked up at the bartender. "Two Kamikazes please."

"I hope it's cheese, they make the best homemade mozzarella." She said. "That's the only reason I ever go in there."

We put the bags on the bar, we opened them, and they were quite full and heavy.

They were full of fireworks.

"What the hell are we gonna do with these?" Alyssa was mad, she was shaking her head. She was shaking the bag, she dipped her hand in and pulled out some sparklers.

"I guess we could save it for July."

"July that's so far away. Not even any mozzarella. Damn!"

So we gave it to the bartender, she said her husband will light them off on the fourth of July, it was five days away, she gave us kamikazes on the house.

***

The End of Part One*

***

*If anyone wants to hear about the other four men from the summer of '88 comment and I will put the stories up... Thanks...