My First Time

 First Time; Sheldon’s Evolution.

Chapter 2

As a boy and teenager, Sheldon had fetish for boots-cowboy boots and wellington boots. He would fantasize  of having a closet full of  beautiful cowboy boots. When Sheldon could drive he could really start to satisfy his fetish. He went to a shoe store and bought a pair of black leather Wellingtons. He got hard just trying them on and almost ejaculated. As soon as he got in the car and sure no one was looking he jacked off. He still had to restrict his purchase to the one pair or his parents would get curious. When he went off to University he bought his first pair of tan cowboy boots.

Sheldon was always attracted to girls with short hair and boys that were slightly femme. Still he saw himself as straight and dated women. He married Chrissy and they enjoyed a good sex life. Chrissy didn’t mind if Sheldon wore his boots while he fucked her. Sometimes he would ask her to lick them. As long as  Sheldon could wear his boots, his sex life was fine. He also picks out boots for his wife to wear while having sex. He likes her in  knee high patent leather ones with high heels.   Sheldon got interested in fashion as he wanted to wear stuff that looked good with his boots. He bought tight designer jeans that he would wear with the jeans tucked into his boots. Sheldon likes a tight fit also for his shirts and jackets.  Sheldon got interested in jewelry and started wearing bracelets, rings and necklaces. He likes beaded bracelets in different colors and wears three or four on his wrist. He got the courage to wear a beautiful pearl necklace. He wears ring with a beautiful blue stone on his right hand. However, Sheldon is always careful in how much jewelry he wearing and not to draw too much attention to himself. Sheldon receives lots of compliments on his dress when he goes  out which makes him feel really good. His wife likes the way Sheldon dresses as well. Let’s face it most men do not dress well, many look like shit.

 He likes wearing different colors and gradually became attracted to wearing purple and pink. Besides wearing cowboy boots likes wearing his Chelsea boots with 2’inch heels. He feels so good in his high heels, they give him a lift. Whatever boot he wears they need to be tight. Sometimes slipping his foot into a tight boot with heels can make him hard.

Sheldon started wearing lots of leather. First, motorcycle jackets then leather jeans. He got the jeans in different colors-black, white, brown and even a pink pair. A pair of tight leather jeans can also make him hard. On his own he rubs his leather crotch and cums. 

Gay men would notice Sheldon, his clothes and boots.

Sheldon started becoming curious about gay sex. He watched gay porn out of curiosity and soon started getting off watching men suck and fuck. Of course he liked seeing men in boots having sex. He enjoyed seeing them lick their partner’s boots before fucking in them. He started to imagine himself having sex with cute guys in boots. These were always gorgeous guys wearing gorgeous boots and high top sneaks. 

Sheldon started to play with his hole. He lubed his fingers and fucked himself with his fingers. It felt so good he went and bought a dildo at a sex shop. It was white and 8’inches. He loved to fuck himself with the dildo. He craved the feeling of the dildo deep inside himself. He  began to imagine some gorgeous guy wearing boots fucking Sheldon.  Sheldon also likes to suck on the dildo imagining bringing some dude to climax in his mouth.   He has to do this stuff when his wife is not around. Gradually he has lost interest in having sex with his wife and just wants to do himself with a dildo.

He is reading a lot of gay stuff, both erotica and stories about gay men and gay culture. His e-reader is filled with this stuff.  He loves reading about beautiful boys making love, sucking and fucking each other. He gets off more on reading gay porn than seeing videos. He likes the detail of some of the wwritten porn which stimulates his imagination. 

 He wakes up in the morning with a hard on and dreaming about a beautiful boy doing down on his cock and giving him a wonderful blowjob. He imagines playing with boy’s hole while having his cock licked and sucked.

 Sheldon is afraid of “coming out”. He believes his family and friends would freak out so is trying to find  different ways of satisfying his queer desires besides using the dildo. He starts going to the gay village to just get comfortable being with gay men. Eventually he met Hank  with him whom he had his first complete experience. Before Hank he met some cute boys in the village. He would drink to relax and start up conversations. One time he was sitting with a beautiful Asian boy and after a while the boy reached over and put his hand on Sheldon’s crotch. Sheldon froze and the boy withdrew his hand. Sheldon apologized and then got up and left. Another time he was talking to a gorgeous  blond boy who was wearing white leather shorts and beautiful high top Nike blazers with blue swoosh. Sheldon was wearing his Chelsea boots. The boy complimented Sheldon on his boots and then put his sneaker on top of them and slowly rubbed them. Sheldon did not freeze this time but just said that he loved the boy’s Nikes. It did not go further than playing a little footsie. Sheldon did have one blow job before he met Hank. He met a gorgeous boy  wearing pink cowboy boots at the village. They talked and hit it off. Sheldon was so turned on by the boy and his pink boots and that when asked if he could come back to boy’s place, Sheldon agreed.   Sheldon got in the car with the boy who started kissing Sheldon. He offered to suck Sheldon’s dick and Sheldon accepted.  He blew Sheldon off in the front seat. It felt great to be blown but Sheldon felt a little guilty  so he thanked the boy and left.  

 It was after these experience that he went to park and met Hank with whom he bottomed and was fully bred for the first time.