First Date

What comes up must cum to come down one way or the other

Hi I’m my name is Craig and it’s just my step mother and myself, and my younger step sister most of the time,due to my dad working with the railroad system. I’d estimate at least 90% of the time. So dad wasn’t around much for a boys fatherly advice, on guy things.
So i went through puberty on my own, watching the Duke’s, Charlie’s Angels, anything i could to see a sexy woman, including steeling glances at my step mom and sister.
I did a lot of masturbating, with thoughts of them in my head. I had a lot of fantasies come to life in my head while taking long showers.
I was getting older and starting to date, and had a date with a girl from our neighborhood, Tiffany.
S he was a very pretty girl with an outgoing personality.this was my first date, after the dance we had an hour or so to kill, so I asked if she wanted to take a ride in the country. Tiffany smiled and shook her head yes. Once we were out of city lights,we could see the stars a lot better. She commented that they were pretty, and asked if we could stop and look at them. “Yeah,sure” i said looking for a place to pull over.
Finding a safe, flat place making sure not to pull into a deep ditch. We both got out, heading towards the front of the car, I said to her “it’s a nice night out”. Tiffany grinning at me as we sat on the hood. She began to point out the different stars to me, I couldn’t see one she was pointing out, so moving closer to her, with our cheeks almost touching. I finally made it out, she turned her head as I turned mine towards her. Our lips only a few inches away from each other’s, looking into her eyes saying, “your eyes are as beautiful as the stars”. We kissed ,it was my first real kiss.
Things quickly escalated, as we laid back on the hood. We was running our hands up and down each other with passion, and desire. She did it, Tiffany made contact with my hard cock covered by only my pants. Up and down she concentrated her attention on it only now,as I was fondling her boobs.
Tiffany moved her hand up this time, just a little bit higher. She stopped at the button of my pants, we both were silent not even a breath was heard. The button was undone, her other hand joined to unzip them, then I felt it, her warm hand was softly wrapped around my hard cock. She slowly, and nervously began to pump it up and down.
Tiffany moved her head to my chest, so she could watch my cock while she stroked it. I swear she must have read my mind, when she moved her head even closer. I felt the warmth of her breath on my cock,as she continued to stroke me for what seemed like hours, but in fact were only minutes. My heart raced as she moved even closer, then I felt it,her tongue on the tip of my cock. I jerked upwards,and her lips were around the top of the head.
She quickly pulled away and almost crying telling me “I can’t do it,not yet anyway”.
Man I was let down,but it was close to our deadline of being home. We had to be leaving anyhow.
All the way home, she apologized over and over telling me she had never done anything likes this ever before and that she didn’t know what came over her. ,”I’m not a tease,I really wanted to but”. And she went silent.
Nice i thought to myself, I’m the only one she stopped with, that made me feel better. I dropped her off,and even walked her to the door. At the door before she went in she said ,”I really do like you, and hope to see you again,” then kissed me good night.
Well now I was confused I liked her to, but that isn’t a way to show it. Well I arrived home went in, not realizing that I still had a noticable bulge in my pants, and of course my sister noticed, saying out loud “looks like someone had a real good time tonight”. I followed her gaze straight to my cock, I looked back up only to find my step Mom was now looking at the bulge in my pants.
All i had left is to get up stairs to my room, the faster the better. During my escape, I heard Mom scolding my sister. Now what, I couldn’t go to the bathroom, they’d surly know what was going on. So I laid there and actually started to get hard, remembering Tiffany’s soft hand and the wetness of her mouth, then my sister and mom looking at my cock covered by my pants. Wondering if they were imagining what it looked like.
Then a knock on my door grabbed my attention along with my step Mom’s voice, asking if she could come in. I yelled back “I’m getting ready for bed” Judy, my step Mom told me to get in bed then she wanted to talk to me.
I got into bed and told her I was in bed now, Judy came in and sat on the edge of my bed saying, “about what happened downstairs, it’s completely natural and normal for a young man to, ahh, and well get aroused”. She continued saying “Well with hormones,and adrenaline running wild with a new emotional, and umm a physical experience”. Then told me i had nothing to be embarrassed or ashamed of.
Judy told me that she knew what she signed up for, with my dad being gone a lot and that she also knew the day would come that she would need to have this talk with me,and asked “did you wear protection”? ,”What”! I exclaimed,”I mean no,we didn’t do anything, well kinda didn’t do anything”
Judy asked me what I meant by kinda, and again told me that I could tell her or talk to her about anything. So I let her have it all. Everything that happened, including how I really felt when I realized that she and my sister was looking at me.
Afterwards she sat there and took it all in. Processing it in silence. Then tapping my leg softly telling me that she was better suited for this talk than my Dad was anyways. Then she told me that we should continue this down stairs, after my sister went to bed.
About two hours later I got a text from Judy,asking me to come down. I pulled my running shorts on and headed down. I see the only light on was the dim glow of the game room in the basement. I head that way, Judy had a beer, asking me if I wanted one,, “sure” I said
We talked for a while, and she was a big help.
Telling me about girls. She also thought Tiffany was a virgin. not knowing how to express that she liked me with out being physical about it. Judy explained that she probably wanted to finish it, but got scared. Then pointed out the kiss at the door, and what Tiffany had said, it all made since now, even the soft hug.
My step Mom told me that I’d just have to be patient with her, and very understanding.” So I get sexually frustrated to fall in love”? I asked. Judy lagged and told me, “no not at all”. So how do I deal with it,”adding,”just run to the bathroom after every date before anyone can see me”?
“I’ve given that some thought too ,and I might have a solution.” she says getting up. Judy went up to check on my sister.
When she returned, I was up getting a beer, Judy asked for one as well. Turning around with the beer, noticing I was getting aroused,saying to me as I handed the beer to her, ‘looks like you have a very vivid memory of the nights events”.
I must have blushed, because as I sat back down. She stood and followed me to my chair. I had head down so as not to look at her. My step mom squatted down to look up at me,with one hand softly resting on my knee,and the other cradling my chin, saying “it’s normal and you shouldn’t be embarrassed”. “Infact”, she paused “in fact some women would take it as a compliment,and I know I do” she finished.
And began to softly run her hands up and down my thighs. I couldn’t help it, my cock grew harder as she continues. There wasn’t no hiding it either.
Judy slid her hands further up the legs of my shorts,untill I was completely hard, and it was standing straight up now. With one hand went lower to gently massage my balls, the other went to the bace of my cock. Grasping it with a little squeeze,ran her hand up the hard shaft.
She reached the tip, feeling the clear wet thick precum oozing from me, my step mother ran her thumb over it to wipe away. My cock twitched,as she giggled taking her thumb to her mouth sucking it from her thumb.
“Mmmmmm”,not bad,hut i bet it’s a lot better coming straight from the source” pulling my shorts down. She slowly lowers her head to the tip of my cock, never loosing eye contact. She was still stroking upwards on my shaft to bring more out.
Saying “Mmmmm, definitely better”. Opening her mouth to suck the head into her mouth. Judy stroked my shaft firmly,yet softly,sucking my precum into her mouth as it was coaxed to the tip of my cock with her soft hand.
She took me into her mouth completely.and began to move her head up and down with some swirls of her tongue around the head, it didn’t take long before I was feeling a tingle rising up my shaft. My whole body started to tense up, my cock swelled even harder. I moaned. “I’m going to cum, Mom, I can’t hold it”.
She just moaned and kept pumping my cock with her mouth and hand. I involuntarily jerked my hips up to greet the source of the pleasure I was receiving. She slowed down,but kept pumping away .with one last jerk up and into her mouth, I felt my cum shoot from my balls.
Feeling my cock contract an pump another shot into her mouth, and with a series of short quick jerks, my cock pumped it’s cum into her warm wet mouth. Finishing up with some slow licks and several soft sucking baby kisses all over my cock. Judy looked at me asking, “do you think this will help,when your left high and dry”?

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