At that time I was about 13-14 years old. My dad worked through the night, he barely was home. He worked from 7am untill 1am. I hardly ever saw him. My mom died giving birth to me, so I just know her from pictures. After 5 years from my mom's death, he married my step-mom Kate. She was blond, with a blond atitude, abit stupid and very sexy. She had a very strange job... She would work for 5 days without coming home, and then have 2 days off. We lived in an old apartment bilding and we only had 2 rooms, a kitchen and 1 bathroom. I had a room to myself. My step-mom and dad lived in the living room.
One night I was watching the Playboy channel on TV and I got realy turned on. I knew my step-mom still had 2 days of work remaining, and my dad went to a convention. I've been always ashamed of my cock, it was petite, small and had tons of hair on it. It was big enough to see it through my pants when it was hard. After a while of watching sexy women, I was realy turned on. The TV was in the living room, and so was all my parent's stuff. So I walked to my step-moms drawer and found lots of thongs. I haven't seen so much in my life. There were blue, black, small, big.. I only found 2 pairs of normal underwear in that drawer. I decided to put a thong on and see how it fits.. It was uncomfortable to put them on, they were a bit too small for me. When I put them on, it felt wierd... I never felt something that close to my ass. The thong was too small for me, and alot of my hair was outside the thong area, so were my balls. Then I saw the bra drawer and decided to put one on. It was also a bit too small but when I put it on, it felt great. I honestly don't know why, but it did. Then I decided to put stockings on.. It was strange putting them on, something like big socks. I looked at myself in the mirror, and I felt sexy. I found a mini skirt in her drawer.. It was seriously the smallest mini skirt I have EVER seen. I watched porn alot and that mini skirt was realy, realy small. I put it on. I felt like a slut, but I still wasn't finished. I found a sexy lingerie-type top, I put on high heels and walked around the apartment. I washed my ass-hole and cleaned it. Then I went to the living room, and turned the thong abit, so I could stick my finger up my ass. At first It hurt.. But when I inserted my finger more and more, it felt amazing... I kept inserting it for about 5 minutes, and my ass started to hurt abit. Then I decided to take a break and search for kinky stuff in my step-moms closet. After what seemed like ages, I found a vibrator, a dildo and a strapon. I knew that she had a viibrator, my dad kept making jokes of it, but I wasn't sure if he was just joking or saying that she had it.. I looked at the vib, the feeling holding it was amazing.. I stroked it... God it was beautyfull.. I turned the vibration on and tried to stick it my ass.. But it was too big. The dildo was smaller, so I decided to try my luck with it. It realy hurt at first, but it also felt realy good.. I kept masterbating my ass for a while, and heard someone unlocking the front door. I was scared, and I felt a strange feeling in my tummy. I was still wearing my step-moms lingerie and the dildo, vibrator and strap-on were on the floor. I panicked.. I scooped everything up and ran for the bathroom. I close it in time, because I heard my step-mom walking into the apartment. What the hell was she doing here?? She was supposed to work for 2 days...
"Kevin? Kevin? KEVIN!!!!!!" - she yelled. From the tone I knew that she was pissed of. "Kevin, what the fuck were you doing in my closet?!!!!!!!!!!!!!"
I was scared, I never was that scared in my life. She knew that I was in the bathroom, so she walked near the door, I could hear that she was breathing loudly, and I knew she was angry. She kicked the door
"Kevin!!!!! Get your ass out here right now!!" - she yelled..
I didn't have any choise but to go out.. As I unlocked the door, I felt ashamed of myself.. I was a boy dressed in womens lingerie.. As I walked out, she looked at me.
"You look sexy" - she said.
I was confused, and didn't understand what she said. Did she tell my I looked sexy?? She was wearing a skirt, a bit above her knees.
"W-w-what?" - I said
"You look like a beauty, come with me" - and she led the way into the living room. I was shocked and stood near the bathroom door for a second, and then went with her.. When I came in, she was looking for something in her closet. I felt wierd.. I was in her lingerie, and clothes, and she just said I looked sexy. I though she would kill me. After a while she came up to me.
"Listen Kev, I know your a boy and want sex and girls, but taking my clothes isn't right."
"Sorry... Please forgive me.."
"Can I .. ermm... ask you.. a.. a... favour?"
"Well... I havn't... Seen..... Never mind... forget it..."
"No, tell me"
"I'm ashamed.. And you would say no.."
"Tell me. It can't be more wierd then this"
We both laughed.
"Ok.. But don't tell your father this... I realy want to see your cock."
"Well, I know that your a virgin.."
"How do you know????"
"Call it womens intuition, 6-th sence or something, but I just know. I realy want to see a young boys cock."
"Please.. This is more strange then me dressing up like a prostitute"
"Come on Kev... Please, please please" - She was begging like a little girl
"Well... I will, if you do something for me"
"And what will that be?"
"Strip in front of me"
"What?!" - she cried and jumped of the bed
"Well if you want to see my cock, then do it. And do it nice and sexy"
She stood there for a while, and then she said "Ok.."
Oh-mi-god!!! Did she say OK?!??!?! This was my dreams coming true.
She turned on the stereo set and began dancing. She slid her finger underneath her skirt, and what I say, it looked like she was rubbing her pussy. Then she slid her finger back up to the top, and took of her top. She wans't wearing a bra, so her boobs banged into each other. It was hard not to laugh. Ten she squezed them for a bit. I blinked hard. Was I dreaming?? She was unziping her skirt, and it fell to the ground. She was wearing the sexiest thong I've ever seen. It was black with ornaments on it. It looked realy sexy. I haven't noticed, but my cocks was so hard, that it began to hurt. She saw it and walked to me. She unziped my pants and took them off, also taking off my boxer shorts. There it was, the embarrising thing in my life... My small dick.
"Don't worry, it will still grow" - she said if she was reading my mind.
She started jerking it off, and it felt good.. I moaned loudly.. It was the first time someone actualy did this for me, and it felt amazing. My head was tilted backwards and I close my eyes. Then I felt something wet. I thought to myself "I cant be cumming, its too early and I would feel it". I locked down and I saw her sucking my petite dick. She could easily put my entire dick in my mouth. I was still wearing her lingerie, and she was still in her thong.
"Lets move on the bed" - i suggested.
"Lets" - she said.
Then I took my bra off, the top, the stocking and the thong. I was naked, and she was still wearing the thong. She understood that I wanted to see her naked, so she also took her thong off. We were both naked. I realy wanted to see her pussy up close, so I bent over to her and saw her wet, smelly pussy. She shaved. I licked it and she moaned. It felt good for me also, because it was the first time I heard a women moan. I started licking it wildly and she grabbed my hair and pulled hard against her pussy. I saw her clit. And rubbed it. She moaned so loudly, that i almost jumped. I kept licking her, and then she tilted herself abit, so she could suck my cock. We were in a 69 position. That was amazing, we were both moaning and both sucking. After a while she stopped sucking my cock, and I looked up at her. She was at the end of the bed, and her pussy was spread wide. I understood, she wanted my little cock inside her.
"Fuck me kev" - she said in a low, sexy voice.
I went up to her, and inserted my cock in her pussy. For some reason, she moaned. And she looked realy pleased. I though that she was faking, because my cock was so small, that I thought that she wont even feel it. I started pumping realy fast, and just a minute later, I felt that I will cum.
"Can I cum inside you?" - i asked without any breath
"Please do" - she answerd
And she started rubbing her clit. And then I cummed... I never EVER cummed so much in my life. And It felt amazing. I backed up my cock from her pussy and I could see the my cum dripping from her pussy. She started to moan loudly and panting realy fast. She was about to have an orgasim. I wanted to taste her cum, so I bent over her pussy and licked it. She understood what I wanted. And then she cummed. So SO much cum, Jesus christ I thought, that women has alot of it. And most of it splaterd in every direction exept my mouht. But the last part came directly on me. And I swalload it.. It felt... Good, I never thought it would taste that good. We were both flushed and we both had sex. We kept sucking and fucking all night. And we fell asleap with my cock in her pussy