My Sissy Diary
- 3 years ago
- 16
- 0
Chubby Sissy Life Diary Part 1 free porn video
This story is derived from events of my upbringing and my journey of crossdressing. I was always a skinny toddler and that carried on until I was in 5th grade when I started to get chubby in very specific areas. My boy breasts were very big like they were large enough to be considered busty in comparison to the rest of my body. I had a little tummy some chubby thighs and an extra big butt that stuck out like a shelf when I would stand up straight. Clothing was super hard to shop for because certain shirts would have my moobs whipping around like a baywatch clip. I didn’t really pay much mind to my moobs until my best buddies began commenting and groping me. We would hangout every single day in the summer swimming and my friends pool where we would act like curious boys without any judgement. We used to compare cocks, masterbate in the same room, and share beds which meant nothing to my other friends but everything to me. My one friend Tyler whose house was the hangout was chubby like me but even heavier and had large moobs and stomach but both stuck out the same and had proportion to each other. Tyler was my BFF like we would fight for each other and nothing ever separated us. Tyler would share the bed with me in deep sleep I would press my butt on his crotch and remain there until I fell asleep. He would often times seem awake when I would force a spoon on him and he often times would oblige. I remember one night we both got drunk and I spilled beer all over my pants so I had to borrow one of his underwear and we shared the bed that night. I waited for Tyler to go to sleep and nudged my butt into his crotch and his cock was hard and completely sticking out of his boxers now resting on the ridge of my butt cheeks. It excites me to have my first hard cock resting on my ass so pushed against it slightly more and the rock hard fat cock pushed its way between my buttcheeks. I knew Tyler had a very thick cock from our playful antics when we hung out. He was slightly obese, hairy Italian, 5’10 300 7c very fat even when flaccid. He wasn’t confident at all but didn’t seem to be gay or bisexual. I didn’t sleep enjoying the feeling of his throbbing cock as his breathing began to quicken I knew he was about to adjust his sleeping position. He pushed his crotch painfully into my ass half a sleep causing me to jerk waking him up. He impaled me in his own underwear accidentally and blew a huge load all over my ass and mostly between my butt cheeks on the boxer seem. He had no idea his cock was out and when he discovered he felt the cum all over his crotch and said to me “dude check the bed I think I had a wet dream!” I hopped up with a boner myself with cum marks on my crotch and literally all over my ass the boxers were ruined. He pointed at my ass and said “fuck man I’m sorry think I gave your ass a facial” I blushed and said “it’s ok man I really don’t mind and it’s your boxers anyway” at this point Tyler noticed my cum print and boner. He pointed and laughed teasing me and a few jokes about me asking Tyler to pay me for using my butt. When we laid back down I went into the bathroom and fingered my butt as I masterbated thinking about Tyler’s cock. We woke up in the morning laughing about what happened and it was a very very hot day. Tyler’s brother Vin and his BFF Frank were at the house and got us into swimming. I always got nervous swimming because my moob to stomach ratio was so off that I looked like a female flashing at times. Frank was a jock but a really cool guy and vin was more reserved and mature the older bro to Tyler was chubby with a full beard at 17 and full body hair. Vin had a very average size cock while frank was the biggest out of our circle. Frank was tall athletic and handsome. Frank and I would play wrestle a lot and I enjoyed it because even out weighing him he could still overpower and manhandle me. We all went to the pool I removed my shirt pretending to stretch walking to the pool to reduce my breast visibility. We all hop in and we’re playing games in the pool until we hear the gate shut. Giancarlo was vin and Frank’s friend and also a skinny small k** with a bully mentality. As G walks up he says “I didn’t know you guys had girls over I love titties” and everyone but Tyler laughs. I absolutely loved being humiliated about my body but none of my friends knew that. I would often times fight with G just to hear the things he would say to me. This day I would take things too far with Giancarlo and I would learn to not judge a book by its cover. Giancarlo began pinching my moobs teasing me so failing on many of my comebacks I decided to take it personal. G was a tough short skinny boy afraid of no one but met his match in front of most of the school when he got his nose busted by a girl with a chair years back. I decided to bring that up and G snapped on me. Across the pool he told me I was dead so I climbed out of the pool and heading over the deck not knowing fast little Giancarlo was already right behind me and he pushed me when I was running down the deck steps causing me to fall on the driveway taking my breath away. He jumped down and pulled my shorts off throwing them on top of Tyler’s garage. Vin and frank hysterically laughing rooting him out he sits on my naked back holding my arms behind my back. Degrading me about my weight, my cock size, my moobs, and this all turned me on so much. He finally let me up and my naked body is covered in dirt and pebbles. I cuffed my cock and ran for the house. To be continued
Myra
- 08.06.2022
- 12
- 0
