Donnie, the kid next door, I’d known since he was 12. My wife and I live next door. Donnie would come over a lot, sometimes to help out on some work we needed, other times just to hang out. He liked hanging in the basement with me. When he was about 14 his shorts slipped down as he was bending over and I noticed a pair of womens panties he had on. I wasn’t going to embarrass him but after the fourth time bending over, and another of his spreading his legs, so I could see them up the legs of his shorts I just asked. Yes they were panties. He likes to wear his sisters panties and she knows and helps him.
As time went on he would act more feminine when we were together downstairs. At 15 he actually asked me if I wanted him to suck my cock. I told him no, and that he should be more cautious about being that outward in our neighborhood. Someone might take the wrong meaning and take offense. It’s a pretty conservative area, though I’m not part of them. He told me that he only felt comfortable like this (meaning dressing in girls panties) around me and his sister. I asked if he’d ever sucked anyones cock or gotten fucked. He said he had not but wanted to. He just wanted to see what it was like. He said he didn’t know if he was gay or not, he didn’t know. I mentioned that just crossdressing doesn’t make him gay. I asked about him and his sister, and she’d giving him blowjob instructions using a cucumber when no one was around. When they had the house to themselves, she’d get him dressed in her undies and skirts, stockings, blouse, heels. I asked if he had any pictures. He had his sister take some pictures of him as well as some she posed for.
A month ago it happened. He was showing me pictures, he looked very much like his sister, Hiding his cock he showed his ass, him in undies and others nude. Then he showed me pictures of his sister nude and in lingerie. They were practically twins except she had B cup tits, and he did have little puffies on his chest. I asked if he’d had sex or given BJs yet and he said he had not, he was waiting for me. I reminded him I was married and had a sexual outlet, one with a mouth, a pussy and an asshole I could fuck. “Do you like fucking her in her asshole better than her pussy?” he asked. I told him in a way I did, but she couldn’t take it too much as it caused her some problems, but she still allowed me to do it. “I’d let you do it” he told me. I just told him it wasn’t a good idea. He went into the bathroom and came out in white sheer panties and matching bra. The panties were over a white garter with tan stockings. I knew he had on makeup but he redid his eyes and put on fresh lipstick.
As he came out he was turning around showing me his ass which was so damn cute, tight, and little but perfectly shaped I couldn’t help it. I grabbed my crotch and told him that if he didn’t leave right then he might not be the same when he left after I was through with him. I laughed at me then smiled and pursed his lips like a kiss to me. “If I do this I’m not going to be gentle, I’m not going to be slow, I’m going to fuck you until I cum in you” he smiled “You fucking bitch” I told him as I moved to him. I ripped off his sisters panties and threw him down on the spare bed we had down there. I stripped and shoved my cock into his mouth “Suck it, suck it like you want to” I told him as he started sucking on me. I got some lotion and was lubing his tight little back pucker, it was really tight he was wincing as i pushed a finger in. I moved out of his mouth, got on top of him, my cock on his ass my arm pushing his shoulders down on the bed. “You’re gonna get fucked bitch, you’re gonna get your fuckhole used” I whispered to him as i lined up my cock to his tiny hole. I’m about 2 inches thick I had to really push as he said “Yes, do it, I want you to do it to me”. I told him back “Fuck you, what do you want me to do, tell me what you want” as I was pushing my cock into his ring. “Fuck me, please fuck me aaaagggghhh” he groaned as my cock pushed in all the way once the tapered head got in.
I pummeled his asshole, he was tearing up and wincing, but not saying anything. “Now you asked for it, just take it bitch. You like this, you want to me a girl? You want to be the one who gets cocks inside your body, who gets fucked? You want me to cum inside you?” I asked and there was no answer. It had been about 7 minutes or so, he was easing up I could tell he wasn’t as tense. “Yes, I want you do it all, cum inside me” he whispered. “You realize that will make you a woman? Someone I can fuck anytime I want, in your mouth or your new pussy, you’re mine” I told him. “oooooohhh YEsssss” was his answer. Then I jammed it into him and shot a 4 day load up his tight little cute ass.
I pulled out and he just laid there. I saw some of my very ample load of cum easing out of his now opened up asshole. “Don’t get any on the bed, my wife will see, go in the bathroom and clean out.” I told him. He went in and came back out with his jeans and tee shirt on. He was walking very gently, very small steps. He looked me in the eyes. “Thanks” he said “I don’t know what to tell my sister about her panties.” he added. “Tell her I ripped them off you and fucked you. You were going to tell her anyway weren’t you?” I asked. “Yes, I tell her everything”. He headed for the stairs. “We’re not done yet” I told him. He asked what I meant. “I mean I’m not done having sex yet. Get your clothes off and suck my cock hard again so I can fuck you again.”. “I don’t think I can, It’s really sore back there”. I told him I didn’t give a shit, he wasn’t going home until I had cum enough, I’d fuck him enough. He just looked at me pleading “Please?”. I told him no. take off the pants and tee and kneel down and suck me hard. Then I bent him over the back of the couch and fucked him again. This time I didn’t let him go to the bathroom. I made him put his pants on, give me the nudes of him and his sister and then leave.
I didn’t see him for about 4 days. Then he came over, and quietly asked if I’d like to go downstairs with him again. I gave him his first load in his mouth, and fucked him again. Now it’s anytime I want I get pussy and ass and mouth from my wife, and ass and boipussy from Donnie.
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