He said that his Scott was really down and he was really worried about him. I said, “Cut the shit Timmy, are you asking me to fuck your friend so he won’t be a virgin and that will give him the confidence to ask out girls?” “Well when you put it that way, I guess I am. I know it’s a stupid idea just forget I said it.” Timmy put his head down like a whipped puppy. I felt bad I had snapped at him so I reached over and stroked his soft cock. “I’m sorry but you had better not have told him that we have been fucking.” “Oh no, I wouldn’t have done that. I know your husband would kill me. I just thought that if you did for him what you’ve done for me it would help his confidence.” The idea taking Timmy’s friend’s virginity intrigued me; I have always had a soft spot for awkward boys and it really pissed me off that the “popular girls” picked on guys like him. While I was lost in thought about Timmy’s friend I hadn’t noticed that Timmy’s dick was back fully hard from my stroking and that I. Her initial assumption of him proved spot on.He was 40, slim and well-dressed but quite shy and it took a lot of sympathetic listening and gentle rubbing of what she considered a nice sized cock, for him to tell his story of what she could do for him and he for her.‘Hazel, for the last 25 years I found that I could only really enjoy sex dressed in women’s lingerie and dresses and skirts. Nearly for all that time I had to use prostitutes because that skinny bitch of a wife thought I was perverted and who in fact didn’t like sex anyway. Your advertisement suggested to me that you might be more open to my fetish. Would I be right in that?’‘You certainly are Howard. And I am looking forward to it. In fact thinking about you fucking me dressed up is making my quite wet. Tell you what, while you are telling me why don’t you caress my lovely wet hairy cunt?’ With that Hazel got up and pulled down her knickers and then sat beside him, her fat cellulite dimpled thighs wide apart to give him.
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