My mom had gave me a drunken hand job years ago but it wasn’t enough and I wanted more.
When I was 12, my mom caught me watching her and my dad have sex. Afterwards, she came in my room to get some answers and somehow it ended up in her giving me a hand job claiming “a good woman always takes care of her man.”
Nothing happened after that between us despite me wishing something had, and even after my dad abandoned us less than a year later, mom’s loneliness sent her down a spiral of depression and alcoholism.
For my 18th birthday, mom got me the best present, she went to rehab and sobered up. I moved in with my cousin, though I barely stayed there since my girlfriend, Chelsea, at the time would sneak me in her room after her mom went to bed and I’d stay with her most nights. By my 19th birthday, mom and I started renting a house together. We moved in and everything was going pretty good.
Chelsea had just dropped me off at home one night after we had a bonfire at a friends house. I was still pretty buzzed from the beer and I tried to hide it when I walked by my mom’s bedroom but she stopped me.
“How was the party?” Mom asked
Before I answered, I could tell she had been drinking as well and was a little disappointed but I tried not to let her know.
“It was good.” I said as I started toward my room. “Oh, Chelsea says ‘hi’.” I added
“Wait! Tell me what’s going on with you guys. How’s the sex?” She asked with a giggle. A very VERY uncharacteristic question from her.
“Really?” I said as I once again tried to leave and was once again stopped.
“Don’t go! Stay and talk, I’m a lonely woman and you’re a handsome young man. Keep me company, please?” She begged continuing her uncharacteristic behavior.
“Let me get out of these clothes, they smell like bonfire smoke.” I said reluctantly agreeing to her begging
I went to my room and put my comfortable clothes on, a thin T-shirt and a pair of boxer briefs. I went to the bathroom and washed my face and brushed my teeth and headed towards mom’s room.
As I entered, she was lying on her side on the far side of her queen size bed. I hadn’t noticed it when I was talking to her a few minutes earlier because she was under the covers but all she was wearing was a blue silk nightgown. It was a very revealing nightgown, her cleavage always showing and it only came down about a third of the way down her thighs. When she would bend over, you could always see her underwear, and there was a time I recall seeing her bend over with no underwear underneath and getting a good glimpse.
I don’t know if she knew it, but that very nightgown is my absolute favorite of hers. She had it as far back as I could remember, and all throughout my teen years living under the same roof as her, I always snooped thru her drawers. I would always wear her lingerie/nightgowns and underwear. I enjoyed masturbating while wearing her clothes. She had a few different dildos. Two vibrators and one non vibrating that had a suction cup. I’m very much bisexual and while normally a top with a guy, I did use her toys on my ass from time to time while wearing her lingerie. I wasn’t sure if Mom was aware of my bisexuality by now and had even caught me once wearing that very nightgown while masturbating. Fortunately I didn’t have her 10” dildo up my ass at the time or things might have been more awkward between us.
As I said, I don’t know if mom knew that was my favorite of her bedroom apparel so I don’t know if this whole charade was planned or just happened the way it happened.
I immediately stopped in my tracks when I saw mom lying on her bed in that nightgown. She patted her hand on the bed signaling for me to come lie beside her. I laid next to her uncomfortably at first. One because I was basically in my underwear, lying next to my mom who was wearing even less, and two because I was trying like hell not to get an erection. I tried.. but the more I thought about NOT getting hard, the harder I got.
I tried not to draw attention to the growing problem in my pants by keeping the conversation flowing and steering it away from my sex life. It was working, or that is to say I thought it was working until I caught her eyes looking down at it for a second or two. She pretended not to be looking but it immediately made things awkward and uncomfortable in the room.
“Do you remember the time I caught you spying on your dad and I having sex?” She asked
“Of course I do.” I responded without making eye contact.
“Lemme see it.”
“See what?” I asked
“Your penis, dick, dong, whatever you call it.” She explained with a chuckle
“What?! Why?!” I asked squirming a bit
“You let me touch it back then, now you won’t even let me see it?” She asked still grinning. “I haven’t seen a real penis in over 6 years, at the very least humor me.” She continued
I thought about it. The truth is I wanted to pull it out the minute I saw her lying in bed with that beautiful silky blue nightgown on but I didn’t want her to know that. She’s my mom. I know most boys fantasize about their mom and they’re like a blueprint for every future lover but I was still ridiculously nervous and conflicted.
My curiosity for what her motives were won over though and I slowly pulled the front of my boxer briefs down. My cock flipped out and stood straight up. Of course it leans to the left and was pointed directly at her.
Mom laid there silently, eyebrows raised.
“What?!” I said while embarrassingly pulling my underwear back up.
“Nothing.” She said almost as if she instantly sobered up. “I mean like I said, it’s been 6 years since I’ve seen a penis, but, also, you’ve got your father’s genes and then some.” She added putting her hand on my thigh. “That’s an impressive piece of meat, lemme see it again.”
I was less embarrassed this time to pull my briefs down. Once again, it flopped out and pointed straight at her.
“Can I?” She asked softly caressing my thigh
I nodded because I couldn’t verbally speak the words “oh God yes!”
Her hand slid up my thigh and grabbed ahold of the base of my shaft. Her pinky finger was gently swaying back and forth over my balls almost unnoticeably. She squeezed it a bit and moved her thumb up the bottom of my shaft right to the sensitive tip. My knees locked up and my toes curled.
“Relax!” She said softly as she leaned in and put my cock in her mouth.
I tried so hard to calm my body but my whole system locked up.
“You’re so tense. Just relax.” She said
“All I can think about is what if someone finds out. Is this OK?” I said nervously.
“I’m sorry, I didn’t mean to make this uncomfortable. I just thought this could be something we did that was just for us and no one has to know. There’s no way they would.” She explained
“I know, and believe me, I’m very much interested, I’m just scared that it’s too weird and once we cross that line, there’s no going back.” I told her. “Plus I have a girlfriend and it’s cheating on her.”
“I’ve heard you and Chelsea having sex, I’ve heard you and Jason having sex, I’ve caught you masturbating while wearing my underwear, and I don’t know but I’m pretty sure you use my dildos. You’re worried about THIS being weird?” She said with a laugh
Before I could respond, not that I was going to stop her, her argument was overwhelmingly stronger than anything I had, she slid back down and put my cock back in her mouth. This time a shockwave of tingles spread like wildfires thru my body and I sank into the bed much more relaxed. I couldn’t believe how great it felt!
After a few minutes of my cock in her mouth, mom sat up. She started to pull my briefs down to my ankles and I kicked them to the floor. She looked me in the eyes for a moment without saying anything and then threw one leg over me and straddled me.
“What are you doing?!” I asked sitting up a bit
“In for a penny, in for a pound, right?” She said placing her hand on my chest and pushing me back to the bed
“Don’t you want me to wear a condom?” I asked completely giving in to her
“Sweetie, I started menopause a long time ago. No babies are coming out of me anymore.” She answered
I had never had unprotected sex with a woman before. I was so hard thinking about my cock inside her now that I completely lost all ability to think and there was no more resistance from me knowing that she was my mom. I had completely given up to temptation.
She grabbed my shaft and placed it on her slit. She gave it a little wiggle and then sat down on my cock. My eyes rolled back in my head and I felt like I was going to pass out.
“Oh my god your dick is big!” She muttered as she began to grind away.
She didn’t take long before she started to pant and moan. I had spied on my mom and dad many many times and had never heard these noises coming from her before. She was usually fairly quiet. A dirty talker but not a lot of moans and screams.
I ran my hands up her nightgown and grabbed ahold of her 40D breasts. She immediately pulled the nightgown off and threw it aside. It landed on the lamp lighting the room and darkened the entire room a bit.
My hands moved to her hips now in an effort to control her movements from making me cum and her tits were swinging in my face. I reached out my tongue and got ahold of one of her nipples and began sucking.
“Bite it! Suck mommy’s titty!” She demanded putting her hand on the back of my head and holding it there. “BITE IT! You’re gonna make mommy cum!” She yelled loud enough that if the windows were open, the neighbors would’ve heard it. “OH! OOOOH! OH FUCK!!!” She screamed as her body tensed up and she collapsed on top of me burying her face in my neck. “It won’t stop!” She screamed into my neck
“Holy shot!” She gasped springing up and looked me in the eye. “Oh my god I want more!” She added out of breath
“I’m glad you enjoyed that.” I said with a grin. I was very proud of myself.
She sat on me for about 30 seconds or so quietly trying to catch her breath. Every few seconds she’d grind a little and tiny moans would escape her lips. She took a deep breath, sat straight up, ran her fingers thru her sweaty hair. “You gonna bend me over and fuck me some more or what?”
My mom was always such a quiet, respectful woman but what always turned me on about her when I first started spying on my parents fucking was how dirty she was when she was having sex. She always said the dirty, slutty thing you were hoping she’d say.
Without answering her or hesitation I pushed her off my and got behind her. Seeing her on all fours, ass up almost made me explode but I kept it together. I grabbed my cock and pushed it back inside her. My hands grabbed firmly on her hips as I began to thrust slowly. Truth was, I was staring at her asshole the entire time wanting to fuck it.
Mom grabbed hold of the bed frame and lifted herself off the bed a bit, arching her back allowing her tits to swing. I reached down to grab her swinging titty.
“You can play with my tits later, be a man and fuck mommy’s fat ass!” She yelled
I have never been more turned on than I was in that moment. My hand returned to her hip and I started thrusting harder. Of course it was going to make me cum faster thus ending this amazing moment but I couldn’t stop now.
“Harder! Harder! Fuck that pussy!” She cheered me on.
I started to moan and grunt. Just as I thought I was going to explode inside her, she rolled off her knees and turned and faced me. She squeezed the base of my cock as hard as she could and put it in her mouth. She released her tight grip and I shot a hot wad of cum in her mouth. She started to bob her head and suck. I could tell she was swallowing what she could but some started to drip down her chin.
“It won’t stop!” I moaned the same words she just used a minute or two ago.
It was true. I couldn’t stop cumming. I could feel spurt after spurt shooting out and she just kept sucking and swallowing. It was the most intense orgasm I have ever had.
When I finally stopped, she spit out my dick and I collapsed my butt to my heels in exhaustion. Mom wiped the few drops of my cum from her chin and put them in her mouth. She laid down on the bed and again patted it signaling for me to lie next to her. I fell on the pillow and I felt like I could’ve passed out right away.
“Oh my God, Chelsea is a lucky girl!” She said with a laugh. “Did she teach you to fuck like that?!”
“Yeah, I guess so.” I said laughing embarrassingly. “What just happened?” I asked changing the tone
“Sweetie, I’ve done weird kinky sex all my life. You may not want to hear your mom say that, but it sounds like you’re into some weird kinky shit too. Let’s just say when we do this, it’s us doing weird kinky shit.” She explained
“You want to do this again?” I asked surprised
“Don’t you?” She asked equally surprised
“Yeah of course, I just….”
“I just told you I’m into kinky sex all my life, I’ve had more sex with more partners than you’d want to hear, and just got fucked like no one ever before fucked me and it was my son that did it. I’m in my 50’s now and don’t want to go looking for partners. If I’m gonna have sex, it’s gonna be with you or no one now.” She told me
“Is that why you haven’t been dating since dad left? You’re just waiting for me?” I asked
“That first time we crossed this line when you were 12 what did I tell you afterwards?” She asked
“A good woman always takes care of her man?” I said unsure
“Exactly!” She said “I know you have Chelsea and I know about you and Jason, but you’re my only son and I have to take care of you. It’s my job to take care of you, and whatever you need.”
“Well I’m not starved for sex with Chelsea and yeah, Jason and I have been having sex for a few years on and off. I hope you don’t hate me for that, I’m always the top of that makes a difference, but yeah, that was really awesome. I want to be with you as well.” I told her
“First of all, who you fuck is your business and your business alone. Second, it doesn’t matter if you’re top or bottom, what matters is you’re living your life and have found people to connect with. You just fucked my brains out, would it matter if you had a cock up your ass when you did it? NO! Third, I loved every second of what we just did, and I want more.” She explained
“Thanks. I appreciate you having my back. I love you.” I told her
“I love you too, but I don’t think you heard me. I said I want more. I meant now!” She said with a determined look about her as she began to play with my cock again….