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Male Pegging Stories

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My ex-girlfriend used to shove a vibrating, seven-inch dildo up my ass while she blew me. Quickly, this evolved into full-on pegging, i.

Yelena
Age: 47
My sex: Female
I can speak: English
What is my favourite drink: Ale
Favourite music: Reggae
My tattoo: None

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I had a few friends who were girls and I had fantasized about having sex with every one of them, sometimes all at the same time.

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Truth be told, although I had secret crushes on pretty much every girl in school in some sort of way, it was my best friend Ellen I really wanted. Sure, I wanted to have sex with her, but I wanted to be her boyfriend too. The problem was she had a boyfriend already and he was better looking than me, more athletic than me and way more popular than me.

Ironically, Ellen was academically a nerd. I mean she had the highest GPA in the school, but in her senior year she blossomed physically in all ways: she was taller, her breasts had come in and suddenly boys other than me were paying attention.

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Yet, as the senior year started, after spending a summer down in the States away from me, she had become a different girl. The loose sweaters that had hidden the size of her breasts were replaced with tighter sweatshirts and t-shirts that drew major attention to her impressively large breasts for her small, thin frame.

I had always been secretly in love with Ellen, but now it was worse as she suddenly became popular and the more popular boys asked her out. We stayed friends, nothing changed there, but our time together began to dwindle when she got a boyfriend. Worse, Joey had been my bully throughout school and Ellen knew that.

Yet, she insisted he had changed.

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So as I continued to languish in obscurity in my senior year, and my longing for Ellen continued, I now had a new emotion… jealousy. The whole first semester was torture. She dated Joey; she blew Joey; she lost her virginity to Joey; and because I was her harmless best friend she told me everything, oblivious to my unconditional love for her. Multiple masturbation sessions a day some even when she was over but busy doing something else, or I was over at her house; we hung out less than the every day of the past few years, but still at least twice a week, sometimes more.

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Then one day I stumbled on some shemale porn. The scene was a few minutes in, the student making the teacher go down on her at her desk, before the teacher pulled her dress over her head to reveal a big pair of tits, and then pulled her pantyhose down and revealed a big dick.

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It was big and looked somehow natural on the hot woman… tits and a dick. I had always found a vagina, in pictures and porn, kind of gross and confusing. But that cock was mesmerizing… somehow completely appealing and beautiful when attached to a woman and not a guy.

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Sometimes it was shemale porn, other times it was strap-on lesbian porn. Then one day as I watched two sorority girls use their strap-ons on a guy nerd who was spying on them… well, I became curious.

I did want to get fucked by a girl wearing a strap-on, which after some research I learned was called pegging. I was definitely curious about anal sex, although truth be told being a virgin I was curious about all types of sex getting a blow job, licking a pussy, fucking a girlbut from this point on all those fantasies, and I had a lot mostly about Ellenthe main fantasy was now being pegged by a girl, hopefully Ellen.

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I was watching a pegging scene on my laptop and jerking off when she walked into my room. She stopped and froze, staring at me caught in the act. It was actually a hot scene to see the stereotypical nerd take control and just dominate a guy who is used to being in charge.

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His whimpers as she took his anal cherry were so hot, as were the moans that began to escape his lips as the pleasure replaced the pain and lastly, I was close myself when he began begging to be fucked harder. Save my name,and website in this browser for the next time I comment.

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All. Twitter RSS. Sunday, October Desi English. Straight guy is pegged by the girl of his dreams.

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