Dad had died in an army accident when I was eight. Mom had mourned his loss, but was determined to move on. The benefits she received allowed us to live in a little house with a little extra spending money thanks to a part-time job she held at a law-firm as a legal librarian. I hadn't really known my dad that well, but mom would tell me from time to time how he was "a good man", and that she wanted to make sure I grew up to be a good man too. My my mom is a pretty lady. She was a fidgeter, always busy doing something, and as I grew up she did her best to be both father and mother for me.
We played catch, swam, ran, fished; she did everything she thought my dad would have done to teach me about being a man. Through the years, as she tooke me to scout meetings, ballgames and all, she was open with me, we were friends, but she never let me forget that we were parent and child.
As I grew up I became concious of how well developed my mother was. She talked to me of sex when puberty hit and she noticed my morning wood, suggested I go to boxers after talking with one of her brothers. She showed me a few pictures, talked about masturbation, and did as she had always done, helping me cope through life, acting as mother and father. When I actually started masturbating, she told me about lubrication and the next day there was a tube of KY on my bed table. Mom was thirty-eight, and a very good looking thirty-eight.
She was still fit with just a few laugh lines. She dated from time to time, but just hadn't found anyone to stick to. I once worked up the courage to ask her if she had sex when she dated and she smiled, "Sometimes," she said, then ruffled my hair, "but, in the future, that's an innappropriate question, so please don't ask again," and that was the end of it.
I had met Josephine the first day of school this year and we hit it off at once. She was beautiful, soft, and shy, with long flowing hair that framed her face and bright green eyes and full lips.
She liked being around me because I made her laugh. I liked being around her for a lot of reasons, but it was my cock that was putting up most of the votes. When I was around her it'd come to attention in nothing flat, quickly going from flacid to flint, often to my discomfort and embarrasment. I could tell when she walked into a room because my cock would get stiff, raising the flag just for her.
We shared our last class, English, which was normally my best subject, but it was hard to concentrate when she sat next to me. It didn't take long for us to go from friends to holding hands to making out. It was good at first, the occasional chance to fondle her firm tits through her blouse, her tongue probing gently past my lips, mine dancing with hers.
We would hold each other tightly and kiss, her hands on my head, then my shoulders, going down my back and pulling me closer, hot skin radiating through our clothes.
But when I would grow a little bolder, my hand slipping down her back to grab the firm globe of her ass through her skirt, she would break off quickly, looking flustered. At first I figured I had pushed too far.
I didn't want to scare her, so I just slowed it down to a nuzzle or two. I took her home, and as she got out of the car she looked at me wistfully, "I'm sorry, Robert," she said, almost whispering.
Once I got home, Mom was still at work, so I went upstairs, pulled out the KY from the drawer, and jerked off, thinking of the feel of Josephine, her smell, her heat. I came in no time, thick spurts spouting from my cock and landing warm and liquid on my hand. I wiped up the mess, but I was still hard, so I did it again, my hand gliding up and down the long shaft.
It took longer, but all I had to do was think of her lips, her face, her body, and soon I was cumming again. This happened a few more times, each time she would seem a little more adventurous in her kisses, one time moaning as my hand slid under her shirt and touched the soft smooth flesh of her tits, but any time I wenth further south she would pull away, looking nervous, flustered, whispering apologies that were harder to accept each time they were given.
One time I came home frustrated, slamming the door to the garage. I heard my mom call out to me, "Robert? I hardly noticed them. I turned around and hunched forward over the stairrail, doing my best to hide my raging boner. Mom took a careful look at me, then walked forward, "Are you okay?
I shrugged, "Yeah, I just don't want to talk about it now," I stayed hunched, but I've got a good solid cock and when it's loaded and ready it's hard to hide.
Mom looked me over carefully, her hand coming to my face,"Go on, then. Mom would have come up and talked if I had slammed it. I lay down on the bed and just stared at the ceiling for a moment. I wanted to shout, I wanted to cry. I reached down to take off my pants and when I looked down I noticed the dark spot at my bulging crotch!
There was no way to hide it, and I was sure mom had seen it! I pulled my pants down and kicked them across the room, underwear and all, then lay back down, sighed, and pulled out the KY. My cock was hard as a rock. Josephine had that type of effect on me, and I wanted to touch her and wanted her to touch me; my hand soon fell into a steady rhythm stroking my meat.
I had so much pre-cum on my cock I hardly had to add any jelly, and as I stroked I thought about Josephine's tits, peeking out of her blouse, her nipples hard and pointed, her lips brushing my neck.
I thought about what it would be like to pull her blouse off and run my hands down her smooth stomach, slowly reach under her panties and place my hands on her moist pussy. She would reach over, unzip my pants, and pull my rock-hard cock out, look up at me, and smile. Then I was cumming, my head rocking back and forth as my cock fountained milky white cum. It was the hardest I'd cum, and I looked up to see my door open and my mother standing at the door.
For a moment she stared at me, her eyes focusing on my cock as the last of my cum dribbled down the tip and to my balls. She took a deep breath, then looked me in the eye, "I'm sorry. I cleaned up, put another pair of jeans on, and went downstairs. I could feel myself blushing. Mom was sitting on the couch, still in her cleaning clothes. She had a can of soda and there was another, opened, sitting on table near the other end of the couch.
She didn't look angry or mad, just concerned. I sat down and picked up the can and took a long draw from it, still feeling the heat of my blush. I looked at her. I mean, I like Josephine a lot.
She's pretty, she's nice, and she likes me too! I sat down beside her, not knowing what else to say or do. She leaned over and hugged me and I noticed she wasn't wearing a bra, which wasn't unusual when she was cleaning. My cock twitched, getting hard again, and I was embarrassed, but there wasn't much I could do. Her warm fingers stayed there for a moment before withdrawing.
I watched her walk away, ass swaying ever so gently, and for a moment I wondered what it felt like; to touch her, to feel the skin of her legs, her ass, the wetness of her pussy. I had made the offer lightly and she seemed happy that I was happy. She dressed in a comfortable shirt, again with no bra, and a pair of black colottes and bare feet.
Play the host, will you? Until today that had happened a thousand times and I'd never thought of it. She looked me steady in the eye, "Cheer up. You've got a lot to offer a good woman," a teasing smile stole across her lips as she watched me blush, then another kiss and she was out the door.
I felt my cock rising again at the thought of her tits and how soft and warm they had felt as they pushed against my chest. I blushed even harder, "Stop that", I said aloud. That's when the doorbell rang. She had on a white blouse with long puffy sleeves with a woven black leather belt and a blue skirt that flared when she turned. My cock rocketed to attention, already stoked by the memory of my mom's tits. I know she could feel it pressing against her stomach.
She kissed me gently and I took her to the den. She's nice," like the rest of Josephine, I loved her voice. It took me a moment before I could respond. Josephine noticed my looks and blushed, smiling. She cuddled up to me, her lips inches from mine, her green eyes twinkling in the light of the den, "How long will your mother be gone? I knew where my boundaries were, and I enjoyed what I could. Her tongue darted into my mouth, a shy wren. I opened my lips and my tongue sought hers out, playing, teasing, drawing her into my mouth.
Her hands were on my chest, rubbing my nipples through my shirt. My hands fondled her tits through the shirt. She didn't need a bra, and she hadn't worn one. When I closed my thumb and finger on her nipple she moaned and unbuttoned the top of her shirt. Another button, a third, and then her shirt was open and there were her perfect tits, pointed and perky with stiff crinkly nipples.
I reached up with both hands and gently caressed the sides of her soft skin. She straddled my cock, her cunt rubbing up against my hardness. She moaned, then leaned forward, her tits at my face.