Virgin boy goes to the older man who pays $5 for him to give BJs

Older guys 17 and 18 went to him and came out with $5. He gave BJs to young guys and paid. I was only 14 but I went. I got more than I thought

He was 37, very thin, long haired, always effeminate and dressed in short shorts, and croptops. It was well known in the area he gave $5 to teens that would let him blow them. Most wouldn’t go in during the day but snuck in at night. Especially late at night after dates were over and the guys were horned up even more since their dates didn’t put out. I got up my nerve and went to his back door. i was only 14 and had no kind of sex at all. I was nervous and he opened the door in a crop top, that must have been stuffed as it looked like he had tiny tits, and a mini skirt, his garter fasteners were seen holding up his stockings below his dress line. I fumbled and he asked me if I was there for my $5. I said I was, and he asked if I knew what I had to do for the money. I told him I did and he asked me what it was. “Um, you know, you put it in your mouth” I stumbled. “Yes, and?” he asked. “You hold it there till it’s over, I guess” I showed my ignorance. “Do you jack off honey?” he asked. I was terrifically embarrassed saying that I did. “You know that white sperm that shoots out of the end baby?” “YES”. ” I want that in my mouth honey, are you willing to do that for me baby?” “YES”.

I went in and he shut the door. He had me sit in a chair in the living room, the blinds and curtains drawn just a blue light bulb shining in one of the lamps. “Well, pull them down baby, let’s see what you’ve got for me to work my magic on” he said. I stood up and pulled my pants and underpants down. “Nice honey, nice, but how old are you, and don’t lie or you leave right now” he said. I told him my real age and he asked if I’d ever had any kind of sex and I told him no. Then he told me to take all my clothes off and what for him, it would take about 15 minutes, he told me not to jack myself. He put on some older woman younger man porn for me to watch and “Get ready”.

When he came back he was a she. She was made up and really really pretty. I didn’t realize how shapely she was before, she had an hourglass figure. Her clothes were off and she was wearing a negligee sheer black, with black garter and stocking under. She did have boobs, little ones with puffy nipples. She had a small cock with a landing strip of hair rising up from it. I was taken aback and stunned. She took my hand and on the way to her bedroom explained that since I was a virgin, she’d let me get my blowjob and my money, then more money for the “second time”. That was when we’d have real sex she explained. In bed, she let me suck on her little tits, and she sucked on my nipples, kissed me many times, and worked her way down to my cock. I got my first bj in the dim light showing through from the living room blue bulb. I blasted the fullest load I think I’d ever shot before into his mouth, he moved up to me swallowed it and kissed me deep with his tongue. She taught me how to french kiss then, tasting some of my own sperm in her mouth. She kept hold of my cock, while exciting me with my nipples, and hers. Then when I was hard again, she said “Now, you can last longer while we make love”.

She laid on her back and pulled me on top of her between her legs. Pulling up her legs, she reached down and took my cock to her lubed butthole. I pushed in and she gasped. I hesistated. . . “No baby, it feels good, all the way please” she whispered to me. I pushed my 7 thick inches all the way in and she was moaning about how good it felt. She told me to go slow and I slowly started fucking her in and out. After about 20 minutes of her pinching and sucking on my nipples, playing with my ass, fingering my prostate. She was moaning and grunting, I was doing the same “Fuck me baby, fuck me, make my pussy feel so good baby, please fuck me” she kept saying. I was moving faster picking up the pace, and she started using one had on her own little cock. We came together, her on her stomach and me deep inside her back hole. I loved it. It was my first fuck, my first bj, and my first lover. She was so pretty all made up for me, it was like a real woman or girl. We kissed until I grew so soft I fell out of her. “If you want to wait a while, we can do it again” she said “OK” I responded.

I have no idea why I did it, but I moved down to her belly and licked her sperm off her belly and moved up to her face, swallowed and we kissed again. Her tongue feeling and tasting the inside of my mouth now just having eaten her cum. I was ready again, and this time she rolled onto her stomach. “Do it this way this time baby, just something different”. I got on top, she spread her ass with her lingerie up over her ass and stuck my cock into her again. Again, she was groaning, moaning grunting with my thrusts, i was kissing her neck, reaching under her to play with her tits, she moved her head to the side and would kiss me between grunts and groans. I again shot my load up her ass. I felt like I had fucked a woman, first in her mouth, then her pussy, now in her asshole. She gave me everything.

I got up, she got a warm wet cloth and cleaned me up, then helped me dress while she was still in her lingerie. We walked to the back door, “Anytime you want to be with me fully, like this, just come by and let me know. Give me 20 minutes to be ready for you” she said. I said I would and she put $100 in my hand. “That’s for being a good boy, now a good man, and making me feel like a real woman for a change”.

I went back for years, even when I had girls to date, went if they didn’t put out or if they didn’t fuck well, or just because they wouldn’t swallow, or wouldn’t take it up the ass, whatever. I must say I did suck his little cock many times, I didn’t mind for all the good feelings he gave me. I wanted to repay him. I did let him fuck me a few times, but I wasn’t into it, I’d only do it when he was totally femme and to be honest he wasn’t what he wanted. But we tried it. He took my virginity though mouth and ass, and cock too. I went to get my first BJ and $5.

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