My First Time with my Stepfather
My first time was in a hot tub with my step dad.
Well actually he wasn’t my step dad yet, he was just dating my mom at the time. He was living with us and we had a hot tub out back. Because it was secluded enough in our back yard, he and Mom never wore swimsuits except for when we had company. I did. I was sixteen at the time and thought he was hot – he was 22. My mom was 40 and called him her pool boy. I was boy crazy, had just learned how to masturbate and was full of hormones driving me to erotic dreams about desert islands and imaginings about what “it” was like.
So one week my mom was away on a business trip – she worked for United Airlines and was always away – and he and I were chillin’ in the tub. He was naked of course but I always wore a bikini. He started asking me why I wasn’t naked and told me how nice it felt. Eventually he convinced me to try and I said what the heck. I took off my bikini and wow! It DID feel nice, all that warm water gently caressing my skin as I floated naked in the tub. It was probably the start of my nudist career.
So there we were floating around in the hot water, naked, talking. Then he asked me if I’d had sex and how I liked it. Except for a fumbling finger-session with a boy under a blanket on a choir trip bus and being in a sl**ping bag naked with Marcia LaFontayne at a sl**p-over, I hadn’t, but wasn’t going to admit it.
So I said I knew all about sex, although I actually only knew what they taught us in Health class – the basics of what goes in where, etc. So he asked me more questions – about positions and penis’s and (eww!) oral sex. But I said I knew all that stuff.
After a bit of this banter, he said “So do you know what to do with this?” He stood up and I saw my first live, erect cock. I’d seen his penis plenty of times before and it was always limp and not very big. This time, it looked huge. I couldn’t figure out how it would possibly fit in my little 16-year-old pussy. I barely had pubes.
But not wanting to seem immature, I got up on the side of the tub and floated my legs out toward him in the water, so he could put it in like they talked about in class. He came over and started playing with my pussy with his fingers, slipping them in and out. It felt really good.
Like a smart ass , I said. “So aren’t you going to put it in?”
Right question. He spread my legs wider, came close and I could feel the head of his cock at my pussy. He worked it forward and back, getting a little more in each time. Pretty soon he was all the way in, stroking in and out, and I thought, “so this is what fucking is all about.” I remember it felt really nice, It made the hair on my neck stand up. I was surprised it didn’t hurt – it felt like my pussy was glowing.
So I relaxed in the water. His cock held me up on one end and I lay back resting my shoulders and head on the edge of the pool. He fucked me (because I certainly wasn’t doing any of the fucking myself) for a long, leisurely time, then started going faster and harder. I got worried something was wrong and was about to stop him when I suddenly got all slippery inside and he was moaning about “cumming”.
He stayed in me for a while, pumping it in and out, then pulled it out. It had gotten softer and came out easily. He said he’d had an orgasm and asked me if I had one too. I didn’t know what the term orgasm meant and must have looked puzzled because he said, “It’s what you get at the end when you hump the sofa pillow.” I got caught masturbating once and I guess Mom told him about it.
Now, I knew how I got my orgasms but had never had one using anything like a penis, just a pillow.
“How do I have one with a guy?” I asked.
“You put the cock in your pussy and hump it, just like it’s your pillow,” he explained.
I told him I wanted one and could he put his cock in me again. He said we’d have to wait until later. So we got out of the tub and went into the house and I remember we sat on the sofa naked and watched TV and had ice cream. My pussy felt all slippery even after I’d toweled it off. His cum was oozing out of me.
Later, we went to the bedroom and he asked me to make his cock hard again. I didn’t know what to do so he told me to hold it in my hand and squeeze it. I did it for a while but nothing happened, so he said maybe I should put it in my mouth and squeeze it with my lips and my tongue. It sounded gross, but I wanted to seem grown up, so I did it.
His cock was smooth and warm, and I lay on my stomach with my face in his crotch sucking and he put his hands on my head and began pushing it up and down. I caught on pretty quick and I felt his cock getting harder and growing in my mouth. He began to moan and I was afraid he was going to squirt in my mouth and I would miss my orgasm again, so I got on top of him and I slid it inside my pussy.
It was difficult to get the same sensation as masturbating on a pillow by fucking a cock because when I masturbate with a pillow even today it isn’t really like fucking. I turn the pillow on edge and rub my pussy back and forth, pressing my clit against the firm edge of the pillow. I’d use a sofa arm or even the corner of my bedpost sometimes. But with his cock going up in me and not against my clit, it wasn’t working.
I asked him if I could do it my way and he said yes. I let him slide out, and with his cock on his stomach pointing toward his head, I road my pussy up and down on it, like I did on the pillow. His cock was slippery and hot and… IT STARTED WORKING! Pretty soon I was feeling like I did when I masturbated and when it got to feeling better and better, I went faster and harder on his cock.
You should know before I go any further that when I cum, I’ve always made this really embarrassing sound with my throat, like I moan but through my nose and in high pitched little squeals. It sounds all nasal but I can’t help it.
So I could feel myself losing control and was just pounding away up and down the length of his cock. Finally I came, and he must have been able to feel it because at that instant he shifted his body down and rammed his cock deep inside my pussy. Wow, that did it. I kept cuming and cuming and squirting and bouncing to make it keep cuming and squirting.
About when I couldn’t stand it any longer, he started moaning but I couldn’t take the sensation. It was just too intense. I had to pull him out but didn’t know what else I should do after I did it. So I climbed off him and quickly took his cock in my mouth again, thinking if he liked it before, maybe he’d like it again.
His cock tasted like my pussy after I masturbate, and his penis was huge, wet and very warm. My lips and face got wetter and wetter every time I slid down into his pubic hair because I’d completely soaked him. My pussy still throbbed like mad.
I started moving my head up and down on his cock, sliding it in and out of my mouth. I remember how he reacted when I was sucking just the head. He was rolling and moaning a lot when I felt a salty jet of cum spurt into my mouth. It tasted ok, nothing gross, kinda like gravy on my tongue, so I swallowed it each time he squirted. Finally he was done and we lay there on the bed. I was so proud! I had my own special pool boy and felt so grown up!
Afterward we agreed we would do it again whenever Mom was away, and that we would keep it our little secret because she’d be mad if she ever found out. I never let on and she never knew. He and I had lots of fun afternoons after that, and whenever she was gone overnight, we always had ice cream after sex in the hot tub and we walked around naked all over the house. At night, we’d have sex in their bed, and during the day we’d have random sex just about anywhere.
He showed me lots of things: positions, sexual massage techniques, how to do hand jobs and blow jobs. He introduced me to their sex toys and I liked the idea of using Mom’s vibrators. It was like I was sharing something of hers, something with the Mom seal of approval, yet doing something naughty at the same time. When I was alone I’d borrow the vibrator and pretend he was holding it. I liked the taste of his cum too, and to this day I never think a thing about swallowing when somebody cums in my mouth.