Crossdresser first time stories

Added: Calin Prewitt - Date: 12.02.2022 20:40 - Views: 43570 - Clicks: 2576

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.

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. He looked at me and said I was beautiful. 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 beers, Mr. 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. I remember feeling like a little kid as he told me to raise my arms as he took off Crossdresser first time stories 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 Crossdresser first time stories off, it was definitely Mr. Antonik undressing me.

I remained on the bed still, fully naked when his hand groped and fondled my little cock and balls. 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.

Once again, I nodded my head yes.

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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. When I stepped out the shower he had a towel ready and dried me off. 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.

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I was smooth and dry finally. 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.

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. 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.

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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. Antonik said it would help me be more relaxed and I trusted him. 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 Crossdresser first time stories 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. 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.

Antonik told Crossdresser first time stories 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.

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. This content appeared first on new sex story. I suddenly I started to lose my nerve and got scared. 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. 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. 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. 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. 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 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.

His swollen cock had done so much damage, I could feel it swelling up bigger as he was Crossdresser first time stories 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.

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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, Crossdresser first time stories 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. 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.

Crossdresser first time stories

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