First Time With My Best Friend’s Mom
I was seventeen, I had never had sex before but I was spending a lot of my time jerking off in my room with the door closed. I spent much of my time skipping school and hanging out at a friend’s house. I won’t mention his name or his mom’s name here for obvious reasons.
He was the new kid in class and I would go over to his house almost every day to listen to music and watch movies, play video games and stuff like that. His mom was in her early forties, single and went where the work was, so they moved around a lot and they didn’t have many friends.
One morning I stopped by before school while they were still having breakfast. I sat at the kitchen table and watched as his mom served him food and each time she bent over to grab a plate or glass, her shirt would fall forward so that I could see both of her bare breasts hanging there!
These were the first tits I’d ever seen in person and I couldn’t take my eyes off of them. They were probably a c cup and I remember being impressed by how big her dark nipples were! Each ended with a large stubby pencil eraser and they hung so much lower than any girl my age could have.
This woman had already had two children. The way they hung made them look bigger than they actually were and between quick glimpses my imagination was going wild! By the time she noticed what I was staring at, I was pretty hard. She grabbed her shirt collar before my friend could see what was going on and left the room embarrassed.
A few days later I knew my friend was out but I pretended to not know so that I could invite myself in to wait. She was polite and nice but there was also a kind of tension between us. Ever since that morning I was looking at her as a sex symbol. I was picturing her long nipples when she caught me staring at her body. It became obvious what was going happen when she said we couldn’t do this.
I won’t lie, I pretty much begged. I told her that I couldn’t stop thinking about her and that I wanted her to teach me how to fuck.
I think she was a little lonely and pretty horny and enjoying the attention even though she knew this was wrong. I moved toward her as I talked and she backed up slowly until she hit the kitchen counter. Even though she didn’t stop me from kissing her, my hands on her tits over her shirt caused her to inhale sharply and breathe hard, exasperated.
She asked me what experience I had. I told her kissing, frenching and a little touching. Her hand moved over the bulge in my pants feeling how hard she made me. Fumbling with the zipper she finally took me out for a few good strokes and then right there in the middle of their kitchen, she dropped to her knees and took me in her mouth gently.
My first blow job didn’t last longer than five minutes before I was cumming in her mouth. It was too much for me. She knew how to work me and the thought of my friend’s mom on her knees with my hard cock in her mouth was overwhelming.
I don’t know how much I came, but I heard her swallow twice, gulping down my jizz. When I looked down, her lips were wrapped around the head and her tongue tickling me from underneath. She swallowed and kissed the tip of my slit. I was embarrassed but she said I shouldn’t be.
Taking me by the hand, she led me down the hall to her bedroom. I’d never been inside it all the way before. The closest I ever came to entering her bedroom was standing at the door. It was modest, I knew they didn’t have much money, but they were clean and her bed was tidy and small, pushed up against the wall under the window.
She turned and closed the door behind us before pulling her Tshirt over her head and asking me if I liked what I saw the other day. Feeling blood rush back into my cock, I looked down to see the effect she was having on me. I realized that I never zipped up after my kitchen blowjob, but also that maybe I should also take off my clothes.
I said something like, “Yeah, I think you’re really sexy.”
She pushed me onto the bed to sit at the edge as though it were a sofa. My erection was pointed straight up as she straddled me and lowered her tear drop breasts into my face so that I could suck on them. Her pink nubs hardened in my mouth and I moved from left to right as she positioned her hips into the right place and lowered herself onto me.
Her pussy was hot and wet and she did all the work for us both using her thighs to ride me, lifting herself up and the dropping back down, impaling herself on me. She put my hands on her at first, encouraging me to feel her hanging fruits and give them a squeeze so that her soft breast meat squished between my fingers. I was in heaven! I wondered how many other men had been in my position underneath my friend’s mom. How old was she actually? How many men had she slept with?
Every time I squeezed her breasts I got a response; a smile, an appreciative moan or a word of encouragement. “Pinch my nipples,” she whispered as she rolled her big hips in my lap.
With each tweak on her large nipples I noticed her smile and grimace at the same time. “Harder,” she directed me to torment her beautiful hanging teets and I happily complied, clamping down on them a little harder with my thumb and forefinger. She would speed up her rhythm and I could start to feel her get really wet on my cock.
I never felt a woman get slick and wet on my cock before and I was thrilled! I kept squeezing her tough nipples and watching her writhe in ecstasy, begging for more and fucking me like a wild animal!
“I’m going to cum!” She braced herself on my chest so she could grind even harder against me. “Don’t stop! Harder, please! Do it as hard as you can!”
For all I knew at the time, nipples were like buttons and the harder you squeezed them, the faster a woman would cum. I found out with subsequent girlfriends that this wasn’t the case, but at the time I did as requested and clamped down on her brutalized nips as hard as I could and gave them little twists, tugging on them like I was trying to pull them off!
I came inside her in that moment, while watching my first truly deep and exhausted female orgasm ripple through her body in wave after wave of spasming pleasure! It was the sexiest thing I’d ever seen and I couldn’t hold back anymore. I tensed and let my jism explode out of me while I yanking on her nipples like I was milking a cow. The idea that her pain was part of her pleasure was too much for me to process.
We were both drenched in sweat in her steamy little bedroom as she collapsed on top of me, kissing me passionately, grateful and affectionately.
She told me I was a good lay. I’ll never forget that. It was almost six now and her son, my friend would probably be home soon. She told me I should go. I dressed while she lay in bed and felt her sore breasts, smiling. I didn’t want to leave but she said I had to. I asked her if we could do this again and she told me that it probably wasn’t a good idea. Despite that, I did come back a few other times throughout that summer when my friend wasn’t home and his mom taught me a lot about sex but they moved away after that and I never saw her again. He and I reconnected on Facebook recently but they still don’t live near me and I thought it would be weird to ask about his mom.