Raising 'Shy'
Copyright© 2020 by Allyfutzus
Chapter 2: The Business of Behind
Romantic Sex Story: Chapter 2: The Business of Behind - She was the girl who I swore went to grade school with me. She arrived mid year in the class room as the teacher, our favorite nun, seventh grade, introduced her. She seemed extremely shy and something of distrustful. A totally new school environment - she never spoke to anyone. I used to think about her and wonder why someone alluringly attractive seemed so distant. She is the one who haunted me the most throughout the years.
Caution: This Romantic Sex Story contains strong sexual content, including Ma/Fa Consensual Heterosexual True Story Cheating Anal Sex Caution Illustrated
[About to be taught to do anal at the winery with my buddy from grade school during our sharing on Mondays]
We both remained married yet we met, you know, continuing to discuss the past. We had a lot to talk about and so much experimental sex to try out.
“Yes, my wife used to tease me saying I was trying to do anal with her. She would say I was going to try to stick me in the wrong hole. I was not, I swear, but she just kept up talking about it. Never would I do that.” “Well, Shy, my silly timid friend, she was asking for it.” “Nooooo ... can’t be.” “Oh really. Think about it. Why at all otherwise would she keep bringing it up? Really?”
“Huh? O-o-o-o-h.” I gave that some thought before I pushed in her butt plug we’d been playing with and she put the cock ring on me and poured us some more wine.
“You know, we experiment. You learn so you can do this to your wife. You can do all sorts of things to her with the correct approach. Think about it and be a little less shy, maybe?”
I loved my wife, a real life mate. We had been through so much together. She developed a physical problem causing too much pain if we made love and I had to abstain. She made remarks about not caring about sex anymore perhaps to justify her condition. I don’t know but I told my fuck partner Dark Eyes about it.
“I feel so lucky to have connected with you again. I was about going crazy with no one to share with. There was masturbation and stuff like that but certainly not the same. Yet you know we were taught to “offer it up” when we suffered in life. Good old parochial values. Those nuns did a great job messing with our minds. Yeah, they had a real handle on having sex. HAH!”
“If she can’t do vaginal sex why not anal? I mean it does work you know. I know. Don’t tell me. You’re too shy to try it or approach her with it. You poor thing.”
I turned the butt plug very slowly around and around playing with it while thinking. I spoke into her butt crack like I was talking to her directly because I was day dreaming thinking about my wife doing it. She didn’t even like cunnilingus so I had hard time figuring her wanting to do anal. Maybe if I’d just tried one lubricated finger to see her reaction.
I gently pulled on the plug with its reluctance to come out of her anus. It was making me horny because doing anal was always so far out of my reach and now Dark Eyes was letting me do it. All I had to do was pull, pop the cork and stick in my dick.
[Now it was official - I was in the anal-annals of butt fucking with my buddy so generous to let me in and she liked it]