I am 34, good shape, decent looking 6ft. 1in weight 180lbs. Off and on over the years, literally since I was 17 I come back to fuck Vicky. She is now 45, divorced three times, a little plump all over, not overly, grossly fat, just plump, I guess thick. She has really big tits EE cups, and loves them played with and sucked hard. When I say hard, she likes it when they get bruised. She is a three hole woman and at 17 she was my first time anal and only my second fuck and suck. I’m without a partner now, so I go see her quite a bit just to get off. She knows that is why I go to her and she doesn’t care. She isn’t the best looker on the planet either. I go over and we may have dinner with her daughter (17 and unattractive, chubby with big tits also) and her son (15 and quite feminine acting). After, sitting in the living room, watching TV or a movie, she will initiate sex, and started getting naked and wanting to suck or get fucked right there. The kids look occasionally, especially when she screams (she’s a loud cummer) but otherwise pay no attention. She says they’ve watched her get fucked from a young age. It takes a while getting used to it but . . .
So she starts in on me, Tam the daughter is just wearing a robe that she purposely opens up fresh from the shower, and shows me her big tits with darker nipples than her mom, and an equally wild, hairy brown bush on her twat. Dee the son, just in tight shorts that shows a super hot looking ass with incredible legs, and a tight top that seems like a girls tubetop. We’re there on the couch, the others in chairs. I told her to roll over, Vicky is totally naked now her big tits moving around, and I tell her to roll over on her stomach. I want to buttfuck her. She can actually cum from getting buttfucked if I pinch and roll her nipples super hard while I am pumping her ass. She in a quite loud whisper says we should go in her room if I want to buttfuck her. Simultaneously the kids say “WHY? Not like we haven’t seen everything else”. Vicky smiles, demuring a bit over being buttfucked in front of the kids. She didn’t know they knew she did that. Tam says “Oh hell, like we haven’t seen you in your bedroom with the door half open getting fucked in the ass. I don’t see how you let guys do that to you, it’s disgusting”. I add that her mom cam cum from it. Both kids didn’t believe it and I told them to watch.
At that I rolled Vicky over and slide into her chubby ass as she moans and inhales deeply. “Watch” I tell them as I start on her nipples and pumping my cock up her ass. She came twice and I came deep inside that well used asshole. The kids really were amazed that she could cum that way. I pulled out and leaned back, “Back when I was 17, your mom was the first woman I ever had anal sex with” I told them. Dee responded “You mean buttfucked”. “yeah I mean buttfucked”. Vicky got up and said she had to go to the toilet. Back after, she brought out a washcloth and wiped my cock and balls off. Tam was very inquisitive while her mom was out of the room, then Dee got into it. Many questions, that you had to go slow the first few times, but then it could get enjoyable for both parties. Dee let out a sigh and Tam looked at him saying “you wish you were the one getting fucked up the butt, don’t you?” and he responded that he’d like to try it.
“Try what?” Vicky asked when she came back. Tam told on Dee that he wanted to try getting buttfucked like a girl, and in some questions we found out that when asked Tam said that she had only sucked on two guys, never had sex in front OR in back. Dee spent the rest of the night acting particularly feminine, even coming and sitting on my lap next to his naked mom. We would both feel and play with her titties I even put his hand on her pussy. He moved it and put it under him on my cock. “Does that interest you more?” Vicky asked her son. I was getting hard. He lifted up trying to put his little butthole on the end of my cock. “You need to lube up you idiot” yelled Tam. His mom agreed. Then told him that for that night I was hers. Not his. That night in bed, we discussed Dee, he was indeed thinking he was gay, wanting to try it. “I don’t want him hurt by someone, or taken like he doesn’t want to be” she said to me. Eventually she told me I should be the one to initiate him. . . if I didn’t mind him being a boy. “Vicky, he’s not really a boy is he?” I asked. No he wasn’t she’d even helped him make up his face, and on halloween he would go out as a girl for several years and kept all the clothes. She would catch him in them on many occasions.
The next day she talked to him about it, and he wanted me to do “the deed”. She bought him girls clothes, makeup, underwear, even a couple of pieces of lingerie. I took him out for ice cream as a young teen girl, in a plaid mini skirt, white blouse, white bra, white cotton panties, and white ankle socks with patent leather flats. She was very pretty, the best legs of any of the real women in the family. It was dark when we got back, Tam was out at a friends. Dee took off his panties in the car and put them in his purse. I made him give them to me as a souvenir of popping his cherry. He liked that. We sat in the car for several minutes kissing and feeling all over each other. When we got in, we went to his room, and there was a soft pale light on, just enough for romance, and a tube of vaseline on the nightstand. Vicky knew I wanted to go in bare and vaseline lasted longer, and since I wasn’t going to use a condom it wouldn’t be a problem. Dee when into the bathroom and came out in white lingerie, very sexy looking, his shoulder length brown hair pulled back in a ponytail, and his pubes trimmed straight up in a two inch wide strip, just the way I mentioned I liked it. I brought him to me, kissed him and told him it would be best first time to spoon behind him and do it that way. It gives us both some control.
His tight little ass opened up like a willing flower wanting juices from a man. I went slow and he adjusted well. Before pumping I asked him if he wanted me to stop, after all even though I was in him, we hadn’t really “done the deed”. He wanted it, he was begging me to “fuck” him. I slow fucked, rocking back and forth for about 10 minutes and he told me to go faster then faster, then harder. I pinched his nipples while I was rapid fucking him and shot my load up his tight little rear. “I feel it, I can feel it coming out of you” he was practically yelling. What we realized after was that there was cum on the sheet, he’d cum while I was fucking him. Kissing him I asked him if he felt OK. “I feel just like I wanted to, you made me into a girl, someone who is with a man”. Not what I was expecting for a first time buttfuck, nor from a young guy but I guess he was truly a trans.
I fucked him again that night, I should say her, I guess. Then the next morning I gave him a mouthful of my cum to swallow. He smiled as he went out to breakfast in his lingerie trailing me naked. Tam looked at us “oh shit, so he’s a real girl now? Not a virgin little queer anymore?”. Her mom shushed her and told her not to talk like that. She asked Dee how it was and he was squeeling in delight.
More on the mom, the now crossdressing son, and I popped the virgin daughter too, in front of her mom and brother, the way she wanted it. That is for part 2
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