Sunday.
I awoke to a text from Thomas at 8:35 am. It read:
“You ready for tonight?”
“Yup, I got everything on the way,” I texted back.
“Sounds great. Text you the location later"
Ordering a dress on a shared Amazon account with my wife was very difficult, but very exciting. The moment Thomas and I turned eighteen, we started to experiment with each other. Everywhere. In the locker rooms after a game. At his home. At mine. Simply make-out sessions.
But, as time passed, he’d borrow his sister’s clothes and make me put them on.
The first time was a simple white shirt, black skirt, and black thigh highs. It was the first time I ever gave a blowjob. His warm and firm cock in my mouth made me feel strange at first until he called me ‘babygirl’ and patted the top of my head gently.
I didn’t know if I was gay or straight or anything at that time. All I wanted to do was please my friend the best way I could. Giving him blowjobs in girl clothes made me feel like those dainty young women in the old porno magazines he and I would steal from his dad and read when we were younger. I developed a crush on him at the start of freshman year, even though I was dating my future wife at the time, Sally.
I sucked on his cock rubbing his ginger pubes with my inexperienced hands. The first time I ever tasted another man’s cum made me feel surprisingly good. He grabbed the back of my head and let out a low helpless moan as he unloaded into my mouth. His seed tasted salty and sweet. Like when you dip a French fry in a smoothie. I kissed the end of his purpled head leaving a hanging line of spit on my lips.
Over time, the outfits and situations would get more complex. I’d pretend to be some girl he thought was hitting on him at the laundromat or the bleach-blonde cheerleader he had a crush on in junior year. I’d wear a wig and something as close to the outfit the actual girls wore and he’d call me their names as I sucked him off.
I guess not seeing my penis helped him more because of my somewhat feminine face. He’d make me wear bikini bottoms and the closest he’d ever gotten to even seeing my penis was when he’d run his finger around my asshole. My chin was smooth and rounded due to my lifelong ability to barely grow facial hair. I had deep green eyes, a nice full head of brown hair, and thick brown eyebrows. At thirty-four, I still looked fairly young. My wife never really called me handsome, but I was always called cute. I was never mistaken for a woman, but I wasn’t necessarily seen as a macho man.
Me and Thomas stopped our sexual exploration when I got married ten years later. I loved Sally. I really did. She had a beautiful smile, long blonde hair, and the biggest blue eyes I ever saw. She made me happy. We made a beautiful daughter and adopted a wonderful son, but deep down inside, I knew who I was. Thomas did too.
Those memories made me subconsciously reach my hand down into my boxers and rub my shaved area. The only time I didn’t shave was my wedding night and when I knew Sally wanted to have sex. I didn’t need her getting suspicious. I kept everything trimmed and neat without having to worry about her because she was out on a business trip. The minute after she left at the beginning of the week, I shaved my whole body. I thought about what me and Thomas would do that night.
I ordered a simple dark brown wavy wig and a red satin dress. It’d been a long time since I felt his lips on mine. Even longer since I wrapped them around his thick, bulky shaft. His eyebrows rising when I ran my tongue around the head. I jerked myself off at the thoughts until I was interrupted by my daughter, Janet. I had accidentally gotten Sally pregnant when she was seventeen. A happy accident.
“Hey, Dad? You awake?” she called out, knocking on the door. I quickly took my hands off my penis and readjusted.
“Yes, honey. What is it?”
“You might want to come downstairs before Milo eats all the pancakes,” she said through the door. I laughed to myself while getting up and getting dressed in a simple white shirt and basketball shorts. “You also got a package.”
I nearly sprinted to the door, opened it, and looked down at my daughter with the package in her hand. When I noticed it was slightly opened, my heart banged against my chest. “Did you order a dress for mom?” she asked. Thank God. She didn’t know.
“First of all,” I said yanking the package out of her hands, “you should know it’s illegal to open packages that don’t belong to you. Secondly, yes, I did order a dress for your mother. It’s a surprise,” I lied. “I’ll be downstairs in two minutes.”
Janet shut the door and walked away. I immediately took out the dress and the wig. I wasn’t entirely sure if it would fit since I ordered a medium. I wasn’t a big man, I was only 5’7 140-something pounds. Now, of course, I wanted to tease Thomas when I saw him, but I didn’t want to get arrested for indecent exposure before I even got to him.
I put both the dress and wig inside the drawer to the right of the bed and went downstairs, trying to control my excitement for the night. I obviously couldn’t walk around the house with an erection. I had no idea where we would go so I guessed he’d tell me later. Breakfast went by quickly leaving me with nothing to do for the rest of the day.
I eventually got a new text message at 9:00 (after what felt like years of waiting) from Thomas.
“I’ll be at the Empire Nightclub on 5th. Look good.”
I was definitely going to look good. I took a quick shower and looked for the soft pair of panties in the dresser on my wife’s side. They felt amazing as I slid them up my smooth long legs. I applied my lipstick in nothing but my wife’s panties until a heard a light knock at the door. I didn’t jump out of my skin because fortunately, I locked it.
“Hey, Dad? I’m going to bed.” Janet said through the door.
“Okay. Goodnight Jan,” I said while looking for my wig.
I added a nice pink blush to my cheeks and applied a smoky shadow wing behind each eye with dark eyeliner and mascara. I’d practiced applying elaborate eye makeup for about a year knowing Thomas would love it. I put on the wig and readjusted a few wild hairs in the back. The sleeveless dress fit nicely except that it didn’t hide my bulge, but that didn’t matter once I had it off me.
I stood five-foot-eleven in my black heels, my long brown hair fell down my back. My deep red lips matched the color of my satin dress. My smooth slender face had well-applied makeup. I knew I looked good. I slipped my wedding ring off my finger and put it under the pillow of my bed. I called myself an Uber, picked up my purse, turned off the light, and left my room.
I snuck past the two rooms avoiding every crack and creak in the floorboards. I saw Janet’s room light on through the crack of the door, but I assumed she simply fell asleep with the light on. I snuck out the front door of her house, got in my driver’s car, and left.
I always wondered what Sally would think if she ever caught me like wearing this. Or what she’d say about me dressing up and going out to meet up (and hopefully fuck) Thomas. She’d never find out. I was going to make sure of that. The driver pulled up to the side of the nightclub. It was huge, took up the whole block and there were at least thirty people waiting outside.
I slammed the car door a little too hard in excitement as I slipped my purse over my shoulder and took my phone out to text Thomas.
“I’m out front.”
“Talk to the big man and give him a name. Go in and meet me upstairs towards the far end of the dance floor. Find the purple door.”
“Got it.”
I walked up to a big, tall, dark-skinned man that had cannons for arms with a clipboard in his hand.
“Name?” he asked. I remembered to raise the pitch of my voice and come up with a fake name.
“Uh, Lucy.”
He skimmed down the clipboard and let me in not a question asked which I appreciated. A few of the people waiting outside gave me dirty looks because I was able to cut the line, but I didn’t care. Walking in I was hit with the smell of roses. It was packed and the shadows of dancing people bounced off the green and purple illuminated walls.
I shuffled past the many people enjoying themselves and made it to the steps going the way I was told. I found the door and knocked on it, my cock stirred ever so slightly in excitement to see my friend with benefits again.
“Come in,” he said.
I opened the door slowly, my hands shaking and my face definitely red from blushing. The room was small and lit up with a single bright lightbulb above a desk in the middle of the room where Thomas stood. To the right was a nice leather couch that sat against the wall.
“Hey, gorgeous,” he said smiling at me and I couldn’t help but smile back. He was wearing a loose-fitting white dress shirt and black pants. I noticed I was swaying back and forth in a girlish way while I white-knuckled my purse.
“C’mere, girl you know I don’t bite.” He said with his gravely yet sexy deep voice. I walked forward and put my purse down. He still towered over me at a burly six foot three inches tall. He grabbed me by the shoulders with his big hands and pulled me closer to him until our noses nearly touched.
“I think I’m going to call you Carla,” he said before kissing me on the forehead. No more Lucy I guess. “You’ve got real good with that makeup. Sal giving you tips?” His thick mustache curled above his top lip as he showed off his big bright toothy smile.
“Well it’s been six years,” I giggled taking in his scent, wrapping my hands around his waist. “You’d think I’d move past the cheap eyeliner you’d find me and tell me to put on by myself,” I joked. He reared his head back slightly and kissed me square on the lips. A soft gentle kiss where I felt the hair on his mustache tickle my top lip. He reached down and grabbed a chunk of my toned ass. (Thank you squat machine.)
I pulled away from the kiss when he ran his finger around the end of my dress around my thigh. “Wait,” I interrupted. He had a confused look on his face. “Aren’t we forgetting something?” I said grabbing his pants and taking off his belt.
“Well, aren’t you ambitious,” he said running his fingers through my hair. I pulled them down his hairy legs as he sat against the desk to prepare for the best blowjob he’d ever get in his life. I was going to make sure of it. I slowly slipped his underwear down and his thick mammoth erection sprang right out at me. I was going to make love to this throbbing familiar member.