First Time Crossdressing And The Aftermath

I am a chunky feminine light-skinned black bottom – I remember when I was first I put on a dress and the aftermath.


It was 1am and I started walking back home from the movies. I was always an outsider. The girls thought I was an effeminate, overweight black nerd and the guys thought I was a faggot, that always poked fun of me and I would never shower after gym class because all the other black guys had sizable dick and they would point and laugh at mine.


I knew my parents didn’t care what time I would arrive home, I was the shame of the family because they knew I was so feminine and hated me for that. On the walk home, I heard a horn beeping behind me, to my surprise it was one of my father’s co-workers from the shop.  He drove up next to me and yelled out the window “Jump in the car, you know buses are not running for another few hours” I opened the door and thanked him for the ride. He asked what the hell I was doing walking around now, at this time of night. I told his I was lonely and went to see a movie by myself. I know my father often joked about me with his work buddies, so the next question Mr. Antonik asked was not a surprise. “Do the other kids ever teased you about your weight or being different?” I told him, yes, all the time. He looked at me and said I was beautiful. Mr. Antonik was the only person over the years I liked because he was always nice to me. Out of nowhere he asked if I wanted a beer, and pointed at the cooler in the back seat. After driving around and drinking 5-6 beers, Mr. Antonik said “You can sleep our guest-house.” “Thank you Mr. Antonik” I slurred out.

Arriving at a small dimly lit house behind a much larger house, he helped me up the stairs and led me to the bedroom. I looked out the window and saw all the lights were out in the main house. He told me the rest of his family was visiting his wife’s mother out of state and the guesthouse is his daughter’s as he led me to a very girly room with a ton of boy band posters on the walls.  I remember feeling like a little kid as he told me to raise my arms as he took off my shirt. He then sat me on the frilly bed as he removed my shoes and socks, then unzipped my pants and pulled them off me. In my hazy fog of alcohol just laid as hands began to remove my underwear, I raised my head to make sure I was not dreaming. I was not dreaming as the beer buzz started to wear off, it was definitely Mr. Antonik undressing me.

He was almost pale white, in his late 50’s, graying hair all over, big strong forearms, hands and a big body to match. I remained on the bed still, fully naked when his hand groped and fondled my little cock and balls. He said his daughter usually lives in the guest house but now she’s off to college. I remembered last year she was a senior and I was still a dopey freshman. She was a little taller than me and a bit on the thicker side with lovely blond hair and beautiful eyes. There were nights I dreamt I was her. Suddenly Mr. Antonik asked if I trusted him and I nodded my head yes, not knowing what he had in mind. He went to the bathroom and returned with a can of Nair and a bath towel and a smaller moist face towel. “I want to see how you look shaved?” “Is that okay?’” he asked. Once again, I nodded my head yes.  After a few minutes of applying the cream under my arms, crotch, and on my legs and thighs, he began to wipe it off with the warm face towel. Next, he told me to stand up, turn my back to him and bend over. Again, I felt the shaving cream being applied to me, but this time on my ass cheeks, butthole and between my legs. This time he told me told me to go shower. When I was in the shower, I wondered what I was doing, but Mr. Antonik was the only person to show me any type of gentleness in such I long time, I liked it and didn’t want to mess it up.  When I stepped out the shower he had a towel ready and dried me off. It felt so loving to have his big strong hands dry me off, but I kept thinking “What the hell is happening to me?!” “This is wrong!” but it didn’t feel wrong at all. He dried off my hair, down my shoulders, then my chest and stomach. He took special care in drying off my chubby butt and between my legs while kissing behind my neck and down my back. I was smooth and dry finally.

Leading me back to his daughter’s bedroom, I saw laid out on the bed was a short blue school-girl style skirt, pink baseball cap, light blue panties and a pink t-shirt. On the side of the bed were a pair of 3-inch heels and thigh high white stockings.  He asked me to put everything on, he showed me so much affection I fought back everything in my head that said this was wrong. I put on the outfit, then he asked me to walk back in forth for him. “You are a real cutie and you black girls have really huge asses!” he said in a thick polish accent. I didn’t know how to feel about that last comment and gave an awkward smile. For the first time since this whole thing began, he started to undress, taking off his pants and shoes, t-shirt and finally underwear. I was with a man that wanted to fuck me like a woman. I just stood there like a lost puppy, because it was the first time a grown man was fully naked with me.

Mr. Antonik was a big man with a funny beer belly. His entire body was covered in black and pepper body hair, but the largest patches of body hair were on his chest. It thinning trail led down to a bushy crotch. Then I focused on that fat polish cock. It was veiny, white and the head was almost a bluish-purple. His thick body hair also crept around his cock and bloated balls. It was so much more bigger and wider than mine and I thought how nice it would be to have a dick like that instead of my little brown pickle.

His intentions were always at the back of my mind, but it finally became real. Sensing my buzz was wearing off, he reached for his pants pockets on the floor and pulled out three little travel bottles of gin, offered them to me, and ordered me to chug all three, which I wolfed down. Mr. Antonik said it would help me be more relaxed and I trusted him. While he sat on the bed, he grabbed some of his daughter’s hand lotion from the dresser and told me he was going to give me a massage to further relax me. He told me to lay next to him on my belly and started rubbing the sweet-smelling lotion over the back of my legs. The lotion made me feel so very feminine and girly as he rubbed it into the back of my calves and thighs. His strong polish hands then lifted the skirt over my shaved cute (his words) ass to my waist, once that happen my little brown hole puckered just a bit. Next, he squirted the bottle and slowly spread it over both cheeks and rubbed it in. I felt a finger sneak its way between my bubble butt cheeks to smooth hole. I jumped a bit, but his calming words relaxed me again. As his finger sunk deeper, I knew I was at the point of no return. A few minutes later his finger was replaced by a wet velvety tongue, and I gave the loudest moan in my life. “You like that my little brown angel?” he chuckled and I moaned in agreement. It was a sensation I never felt before, and it felt so good; I never wanted it to stop. In and out, then all around my he licked, the entire time I uncontrollably puckered and unpuckered.

In my bliss, I didn’t notice he reached again for the lotion, this time smearing a huge glop and the gigantic old polish cock, then squirting a second glob on my soon to be ex-virgin ass cunt. “OMG, I’m about to be fucked!” kept rushing through my mind. Mr. Antonik told me to get up, go over the bed (which was about waist high) and bent over. Not being used to girly shoes, and the alcohol fogging my head again I wobbled stepping over and getting into position. Glancing back, my eyes locked on his now fully erect manhood that was about to make my exit only into a pussy. Leaning over his daughter’s princess bed, and even on 3-inch heel I was still on the tips of my toes. “Beautiful back ass” he kept repeating as he rubbed yet another glob of sweet smelling lotion on my rear. “Never lose one pound” he said further. Next, I felt a large bulbous moist cock head touch my small virgin asshole, as a firm brutish hand pushed back firmly on the bed. “You might want to grip the mattress tightly darling, your hole is very small.”   He said in a heavy voice of a man about to do damage and push me into womanhood.

I suddenly I started to lose my nerve and got scared. “Please be gentle Mr. Antonik” I said just over a whisper. “You feel my cock pressed up against your sissy pussy my black angel?” “Unhmmm” I mouthed. asshole, just know for the first second or two it’s going to feel like you are being split wide open, but only for a second, I promise.” He said in a loving manner.  In my girly voice, I asked again “Please go easy.” I said again as I surrendered my ass to him.

“Relax sweet angel, you are gonna enjoy me making you a woman.” Two beefy hands grabbed my hips and very slowly began pushing his enormous plum sized cockhead into my virgin ass. I did my best not to cry out from the pain, but I couldn’t hold back the initial scream because he hurt me!  He paused for a second, then pressed against my asshole again. I told him it was not ready for this, but he said something to himself in Polish and thrusted in more. We did this to 10 minutes; I would scream, he would stop for a few seconds then push in further. I felt my asshole ripping as my tiny hole was being destroyed. ”AWWWWWWWWW” it hurts so much!!!” a moaned as tears started streaking down my face.  “Just relax and stop crying” then I felt a new moistness, “Am I bleeding?!” I strained out, “A little, but you are doing fine, I promise to clean up you when I am done.” “It won’t hurt for long” as he finally hit bottom. My ass was torn to shreds and I knew that wet feeling was not lotion, it was ass damage, it was blood.

The pain began to subside. He then began sliding his hips from side to side in a wave motion, slowly pushing his huge white cock deeper and deeper again as he started humping my no longer virgin butthole.  He then started to withdraw his cock from my ass slowly, only this time it didn’t hurt as much as his cockhead slide out past my ripped up sissy cunt. Again, he slid his cock into my ass, this time all at once. A shiver came over me as I was being fucked, I started to like the feeling of his cock sliding in and out of my ass. I suddenly realized I was getting a hard-on. As he continued fucking me slow and deep, then a beefy hand started tugging on my little erect pickle, “See angel, I told you I would make it good for you”. “Thank you” was all I could muster as he jammed his Polish meat spear up my ass and jerked me at the same time.  His thrusts began to increase in speed, and with each new thrust working deeper into my now relaxed ass, I began to moan softly. He was making me little sissy faggot and I was okay with that.

“That’s right angel, enjoy your fucking” he said as he was playing with my nipples then moved down to my brown hard short pickle. “You have been such a good girl, you deserve a reward” he said as his engorged blood-stained cock continued to rip open my new ass cunt to bits. His beefy paw jerked me harder and faster until I let out a loud moan; as my cock suddenly shot a huge load. When I masturbated, I had never cum like this…ever! I shot so hard I hit my chubby tummy, his daughter’s dress, her bed and some of my chest. I was incredible. Hearing me moan and squeal and feeling me empty my sack of stored boy cum made Mr. Antonik increase the speed of my anal pounding. Whenever I arched my back, he pushed it back down, whenever he thought I was trying to pull away, he slammed me back with a squishy thud. The pain of the anal tears started to creep in along with the fatigue of being fucked for so long.

It was a pleasure to hear him say “Ready for my seed black angel?!” “Please shoot it…. I’m ready” I panted out in total exhaustion. His swollen cock had done so much damage, I could feel it swelling up bigger as he was breathing more heavily and I knew what that meant. His powerful hands dug into the sides of my hips which brought on a new pain, but that was okay; in a few more seconds I would have a sperm for a real man in me. Suddenly, I felt a new awkward sensation as streams of cum filling my ass, his cock became slicker and slicker as he humped every drop in my wrecked hole. Finally, he stopped fucking me and with his cock rested motionless in my ass as he laid on top of me. His hands interlocked with mine in a passionate moment and I enjoyed the quiet bliss of being a woman.

I could feel his cock slowly begin to go limp, while still gently throbbing a couple times discharging the last remains of sperm in me. Standing up, his cock withdrew from my ass, but he told me to remain in place because I made a mess as he walked to the bathroom. Catching a glimpse of his deflated dirty cock; stained with my guts, blood and shit, I kind of freaked. The was coupled with not being able to close my butthole. After a minute of two of cleaning himself off, he came back with a warm rag. Pulling the up a chair from his daughter’s princess desk set. First, he removed the soiled skirt and dropped it to the floor, it was also stained with dried cum, poop and patched of blood which made me queasy. Next, I felt the warm towel wipe between my legs and balls, after returning to the bathroom to clean it again he started working on my ripped-up butthole. With the skill of a nurse, he gently wiped away the chunks of what was inside of me and cleaned my abused ass. The towel was a disgusting mess. When he was done, he gave me a big hug. “Don’t worry, in a few days you will be good as new and I will buy you your own little girly wardrobe, but I want you to grow your hair much longer…okay?” Hugging him back I said okay. “Time for bed my little angel” he said while letting go of the hug. “Ohhh, first we must change the sheets” he said while looking down at the brownish-red stains on his daughter’s bed. He told me to open the dresser and put on a pair of her panties while he changed the sheets.

When he was done, I laid on the bed and he tucked me in under the covers. He remained in the room after turning off the lights, sitting on the chair. In the dark, I felt his hand continuously rub my sore butt as I drifted off to sleep.