Married crossdresser M 42 paid me to fuck him

I was 18 and still hadn't had any luck with girls to get to have sex. I was so damn horny I couldn't stand it. Mr L down the street was a good friend to my family, I'd known him, his beautiful wife and two kids (younger than me) since I was a kid. I was helping him clean out his garage and basement over a week period. His wife Louise, with the kids, was visiting her family out west for 3 weeks. Sometimes after a hot afternoon in the garage, Mr. L and I would go inside and have a beer. I liked it, he treated me like a friend not "the kid down the street". On the third day I let myself in as I had several times before and I heard moaning from the back of the house. As I turned to the hallway I could see in the open bedroom door. There was Louise from the back, she was in a short nightie, see through thing. Her gorgeous ass moving up and down. She was fucking herself on a big dildo that was mounted to a small table at the foot of the bed. I tried to back up and leave but there was a noise and she turned around. It was Mr. L in his wifes lingerie bouncing up and down on the dildo. He stopped his mouth open his ass totally sitting with the whole, what appeared to be 9 inches, up his ass. "Oh, sorry . . . I'm really sorry. I forgot the time." he said as he raised himself up off the dildo it was suctioned to the top of the low table. I spoke up, apologizing for just coming in but I did hear some noises and thought something might be wrong. "No, nothings wrong. I dress like this when I can, I like it, always have. I was just enjoying myself." I asked him pointing to the dildo.
"Doesn't that hurt?"
"No, when I was young I started with very thin things, my finger then other things. Now, that is normal, Louise even uses that and some vibrators on me sometimes"
"You look just like her"
"Thanks, we have about the same size body, though I do have much smaller tits than she does. She taught me to put on make up. I like it, it makes me feel more in touch with something feminine in me"

He brought out some pictures of Louise naked, getting fucked by him and others. Him in girls clothes, lingerie, underwear and even him bent over with her behind him fucking him. We sat on the bed and I again told him he looked just like her. "do you like me like this?" he asked and I did. I told him he looked really pretty. "You probably date and fuck so many hot young girls, you don't need to have anything with anyone else. Louise would love to have a young guy like you, hell, I'd loved to have you too" with that he reached for my hand. "No, I don't really date anyone" he asked about sex and I told him that my best friend was my hand. He took my hand and put it on his small tit. He was thin but he did have a fatty chest, his pecs were soft like I imagined tits were. "Squeeze" he told me and I did. He wanted to suck me, and I told him I couldn't, I shouldn't. "Look it's just a way to get off, it doesn't make you gay, hell I've had sex with men for four years before I got a girl to give it up to me. It's nothing, just a way to cum that isn't your hand". I still couldn't and he went to a drawer and put $100 in my hand. "Take that, just for not saying anything, and for being so accepting, and telling me that you like the way I look let me do this". In about 10 minutes I was shooting my cum inside his mouth. He swallowed and smiled but didn't let go of my cock. He kept rubbing on me, and soon I was hard again. He got on top of me, pulling down his nightie top to reveal pretty but small tits, with pink nipples. He pushed one to my mouth as I began sucking he reached back and my cock was 7 inches up his ass. He started moving back and forth keeping his tit in my mouth, I started fondling the other one. Then he switched tits in my mouth. All the while I'm now pushing up into him, I'm fucking him. A him that looked exactly like his hot wife, I was finally getting some pussy. I didn't care that it was really a mans ass for that moment as I released his tit and looked up, it was Louise his wife that I was fucking. After about 15 minutes he was moaning and groaning and moving faster back and forth pistoning my cock inside him. "Oh shit, oh shit, damn I can't believe this. shit" he was muttering through his groans. "Ooohh Shiiiiitt" and I felt the warmth of liquid on my bare belly. He'd shot his cum on my stomach without even touching his cock. I sped up and within 5 more minutes I came deep inside him.

He was laying heavy on me. He looked up gave me a light peck on the lips, "I've never had that happen before, not without using my hand during it. That was incredible" another peck. "I've never been fucked that good ever, did you like it baby?" he asked. "yes I did, it felt really good, I finally got to cum inside someone, I got to fuck someone" I answered. "Anytime you want OK?" he told me as he got up off me. He was still in the little nightie, I could see his nipples through the see-through material as he pulled up the top. "Excuse me, I need to use the little ladies room" he said as he went into the toilet. He came out I was getting dressed. "since you've seen me now . . and other things !!! There's no need for me not to get dressed in my girly clothes. Do you mind?" he said and I didn't. I watched as he stripped, his little titties bouncing, the ones I was sucking on so madly before. One had a small bruise. "My nipples hurt, you really sucked hard" he said. "sorry about that" I answered. "No don't be. I mean a girls nipples get used, by men, other women, babies, I think sore nipples are part of being a real woman". He put on a garter with stockings, matching panties and bra, short black skirt with a brown - almost see thru top. He put on heels, and we went to the kitchen.

We didn't work that day, instead we stayed in and he cooked, cleaned, did laundry and . . . we fucked. I fucked him 3 more times that day. At the end he gave me $200 and said that was all he could do. I gave it back to him. So for three weeks almost, I was getting laid regularly, he would cum from me fucking him and he was acting more and more like a woman everyday.

I fucked the older crossdresser neighbor who looked like his wife. I got money that first part before he blew me. But the other BJs and sex were for free.