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.
I breathed in and then kissed a small dribble of pre-cum off of him and worked my tongue around the underside of his tip. I slowly moved my mouth forward. I knew I was going to explode soon and ruin the dress, but I didn’t care. My deep red lips wrapped snugly around his shaft. I curled my tongue around his log covering it in my gloopy saliva to ease up on my jaw.
My cock twitched quickly as I fired six and a half maybe seven good shots straight through the panties, soaking the dress in repressed sexual excitement. I knew Thomas was surprised by the sudden mess I’d made all over the place because I felt another dab of pre-cum swirl around in my mouth.
“Holy shit, girl,” Thomas groaned.
I moved faster until my lipstick smeared around the corners of my mouth and drool leaked down my chin. I grabbed the base of his dick with one hand and softly pressure messaged his full balls with the other. I bobbed up and down and moaned gratefully all around his veiny dick. I got so sloppy that my lipstick was now replaced with loads of spit and dripping juices that I’d made with just my mouth and his meat.
Thomas suddenly pulled me off of him, a thick line of spit stuck to my chin.
“Go to the couch and show off for me,” he said before getting off the desk and getting behind it opening a drawer. I kicked my heels off and crawled on my hands and knees to the couch which made the dress ride up the back off my quads and ass revealing my lace black and red panties. I got on top of the couch and shook my ass in the air.
When he didn’t say anything I turned around to see Thomas pulling out a small bottle of baby oil, a light blue butt-plug, and a twelve-ounce bottle of Whiskey. As he rolled the plug in his hand he quickly popped the top off the alcohol and downed about half of it in a minute. He let out a loud burp and threw both the lube and the plug at my feet. I flipped myself over to my back, picked them up, and noticed how warm the plug already was.
“Listen,” Thomas walked towards me and lifted my smooth legs up in the air, rubbing his strong hands all over the insides of my thighs. “Loosen that hole up for me and then jerk yourself off,” he said, but before I could lift my dress up he grabbed my chin and stared straight into my eyes. “You didn’t let me finish. If you cum you’re not getting anything from me. Understand?”
His tone was deadly serious. “Yes, Sir,” I said a little scared.
“Good girl. Get to it.” He walked back to the desk and took another big gulp of Whiskey that would’ve made any normal person cringe. I opened the bottle and swiped up a large glob of it in two of my fingers. I rubbed it around the ring of my bum and a little on the underside of my balls. I slowly inserted the butt plug into my eager hole and moved it around a little, entranced by the slow circular motion and the tight and warm feeling it had in me.
I was snapped out of it by Thomas shouting into his phone which he followed up with another small sip of whiskey. He tried to quiet down, but I could still hear his whisper shouting.
“Can you stop it!?” I could barely make out the voice on the other line.
“Where the hell are you I-” he cut off the voice.
“I’m at work! Fuck!” He ended the call and threw his phone against the desk in rage. He stormed towards me, grabbed me by the shoulders, and kissed me. A rough sloppy kiss. I could taste the alcohol on his tongue as he worked his way down my neck and chest leaving wet spots on my upper body.
“W-Who was that?” I asked even though I was worried he’d yell at me.
“Nobody.” He growled. Suddenly his grabbed the cum stained part of my dress and ripped it. He tore with so much force he also somehow managed to rip my panties straight down the middle revealing my cock. Thomas took off his shirt, kicked off his shoes, and began to masturbate right in front of me.
“What’re you waiting for? Jerk it.”
“Oh right!” I ran my palm over my throbbing head and moved my fingers up and down the base. As we continued our mutual masturbation, Thomas moved his cock closer to my lips. I wanted to taste the small bubble of seed on his swollen head, but he pushed me lower into the couch and pulled the butt plug out of me, leaving my asshole winking.
“Go faster,” he commanded. I stroked as fast as I could under this cock hypnosis. Eventually, he moved closer and let me kiss his tip.
“Get it nice and wet for me.” I let a good bit of drool build up in my mouth and I let it all out all over him. He groaned in appreciation as I drooled like a starving animal all over his dick and balls. Licking and sucking the foreskin and scrotum as if it were a lollipop. I’d moan after every little tug and pull and I didn’t stop until his dick was drenched in my saliva.
“Great job, babygirl.” He picked me up by my armpits and flipped me to the side so the back of my head was facing the arm of the couch.
“Don’t you think I’m a little too old for you to keep calling me babygirl?” I joked. He slid himself onto the couch on his knees, his monster cock right at my lubed-up entrance. He leaned over top of me and smiled.
“I guess you’re too good for pet names now huh?” He laughed kissing me on the jaw. I rubbed the back of his soft fiery hair and pecked him on the nose. The alcohol on his breath would’ve turned me away if I didn’t feel his dick right on my hole.
“I’ve been wanting to fuck you for so long,” he whispered in my ear.
“Why didn’t you do it sooner?” I whispered back. He lifted his head and smiled down at me.
“Because that’d be gay,” he said blank-faced.
“Shut up.” I pulled him into another deep kiss. He slowly slid his cock in me stopping a quarter of the way in. He pulled off of me and kissed me on my forehead.
“You’re nice and tight.” He thrust into me with nice slow pumps and each pump lessened the pain if only a little. He rubbed his thumbs on the sides of my head and ran his fingers through my hair. I felt Thomas roll his hips deep into me until I felt our thighs touch.
“Fuck! Oh God!” I shouted. I felt like my ass was going to tear in half. He moved his dick inside at the pace of a snail going uphill while I gripped the back of his head so hard his face went bright red. I whimpered quietly feeling Thomas start to speed up his plowing of my now definitely reddened anus.
“Good lord this ass. Treating my dick so fucking good,” Thomas said through gritted teeth. My stretched ring squeezed around his fat cock as if it had a mind of its own. Thomas lifted himself up, hoisted my sweaty legs up, and wrapped them around his shoulders. He fucked me lower into the couch, his sweat falling off of him and onto me.
My cock slapped against my stomach with so much force it hurt. My pained whimpers and groans turned into loving and pleasured moans. I ran my hands up and down his sweaty abdomen, feeling the amount of core strength he was using to propel his dick into my asshole. He was fucking my ass like a pussy and I loved it. A bit of drool leaked from my mouth as I watched him ram me.
I felt my cock twitch and I exploded all over myself again. Thomas slowed his assault and watched three long shots of cum stain my dress and two hit my chin. Thomas grabbed the base of my cock and aimed it towards my face. An excited yelp escaped my lips when each long rope of my own cum splattered my lips and in between my nose and eye.
I licked my lips and realized unfortunately that my seed didn’t taste good at all. But, all that did was increase my excitement to taste Thomas’s load so I decided to encourage him. “C'mon, baby, give me your baby batter. It’s been too long since I’ve tasted you,” I begged, staring right in his eyes.
In the background, I could hear the club music from downstairs, but otherwise, the guttural groans from Thomas and the wet slaps coming from my ass were the only sounds coming from this quiet room. Suddenly he slid his dick out of me with a loud squelch and got off the couch quickly.
“O-on your knees...” he said trying his best to save his load. I struggled to slide off the couch, practically falling off and nearly dislocating my shoulder. He aimed his dick right in between my eyes and stroked his shaft. His cock erupted, the first shot grazed my eyebrow and the hairline of my wig. He aimed another shot right on my lips and down my chin, the thick gel dribbling down to my neck. The last shot landing right on my eyelid and upper lip. Thomas tapped his cock on my forehead to get the last bit of his fluids on my face and then backed away from his aerial assault. The butterflies in my stomach were going wild.
“Fuck yeah.” He groaned as I wiped the semen off of my chin and sucked it into my mouth greedily. Thomas patted my head and kissed my cum splattered forehead.
“You should come again tomorrow, babygirl, cause lord knows I will,” he laughed.
“Mmh. You know I will,” I said still hysterical off the fucking I’d received. I finally stood up despite the pain and wrapped my former lover in a big hug.
“Just try to go easy near my rear end okay? I’d like to walk again if you don’t mind.” I gave him a quick peck on the chin.
“Hold up.” Thomas pulled my wig off and ran his fingers through my short brown hair. “I’m thinking red and blue would look great on you.” He rubbed my chin.
“You taking that anti-aging cream stuff? You look fantastic.” He smiled.
“Aw, thanks.” I intentionally lowered my voice since Carla had just technically passed out. It was just me and Thomas. I pulled away from the hug and readjusted my destroyed dress. I planned to walk out as quickly as possible and go home.
“Dude. I brought you extra clothes,” Thomas sniggered at me trying to repair my torn dress and panties. “They’re in the desk.” I stripped down, went to the desk, and got changed in a comfortable plain white tee, blue sweatpants, boxers, and black sneakers. I grabbed my heels, wrapped up the ruined clothes, and put them in my purse.
“See you tomorrow, my friend,” Thomas said as I made my way out. I had a painful hitch in my step as I still felt my ass twitching and gaping from the night of action. I had to walk like a penguin to ease the pain a little bit which I found very difficult when trying to shuffle through a crowd of drunk dancing party-goers.
I was definitely coming back tomorrow.
