SamanthaCD

This is the Gods honest truth about the night I had sex with my mother.

There’s a backstory long enough to fill 10 parts here so instead I’ll just give the gist of it as best I can without rambling.

If you’ve read my previous stories you’d know that I am bisexual. I have a wife and kids and I absolutely adore pussy. However, there is another side of me that equally enjoys dressing up as a woman and having my ass fucked by my boyfriend.

As a boy I was fascinated by sex at an early age. I had a friend named Jaxson that pretty much taught me the basics of sex, either by showing me his dad’s pornography or, more bluntly, just getting naked and fooling around with me. We started that at 9 years old and that continued on and off for the next 10 years.

My fascination lead me to spying on my older sister. She’s 10 years older than I am and I vividly remember watching her thru the crack of the door undress and even “accidentally” walking in on her in the shower.

When I was 10 I woke up and heard my parents having sex in the middle of the night. Instead of being grossed out like most people, I was turned on and started spying on them.

When I was 12, my dad had left my mom and it was just her and I in the house now. She worked a lot and was rarely home. While being home I began snooping through her underwear drawers. Just curious and wanting to see women’s underwear at first but it slowly grew to, “just trying them on to see what it feels like”.

By the time I was 14, I was fully into it. I would steal an air of my mom’s underwear and bra, maybe even a nightgown or even a sexy lingerie piece and I would wear it to bed. I loved wearing women’s clothes because it made me feel sexy and it also made me feel close to my mom. I had gotten so into cross dressing and my mom, that I would wear her clothes and use her dildo on my ass and pretend i was her getting fucked.

By the time I was 20, I had kind of forgot about all of that when girls, and boys, entered my life. Then out of nowhere, my long forgotten fantasy came true.

I was still living at home and it was kind of making it hard to maintain a relationship with someone so I had been single for a good while. I had a few hookups here and there but keeping them around while you share a wall with your mom is difficult.

I came upstairs and passed by my mom’s bedroom and noticed her door opened a crack. Maybe I’m just overly curious but for some reason I can’t walk past an open door without looking inside. As I put my eye up to the door, I saw my mom undressing. All I saw was her in her underwear with no bra. Her back was facing me so I just saw her ass, but it was enough to make me feel that tingle. My mom was 52 at this point and overweight. Not huge but she was a bigger woman.

When she had put her nightgown on, I pulled away from the door and went in my room. I tried to focus on some other things but I couldn’t get the image out of my head. I mean, I didn’t really see anything. Her back was towards me and she had underwear on. Didn’t matter. I saw what I saw and I couldn’t stop thinking about it. I gave in to my urge and played with my dick for a while.

The next morning, she was in the kitchen wearing that same nightgown and it put those images right back into my head. Soon after, she had left for work and instead of going to work myself, I called in sick. I went into her room and just as I did as a kid, I snooped through her drawers. I tried on almost every piece of clothing she had that day. From bras and panties, lingerie, to jeans and sweaters. I eventually put on a pair of her panties and the nightgown she was wearing that morning and masturbated in her bed.

Next day I did the same thing. Called into work and dressed up in her clothes all day. I even put on some of her makeup, like lipstick and eyeliner/shadow. My favorite was a pair of jeans, and a plain white shirt. I added her brown leather jacket and squeezed into her heels. I stared at myself in the mirror for 10 minutes in awe. I’m sure to anyone else I was a masculine mess but I thought I was sexy as fuck! I even took a few pics of me each one with one less piece of clothing on. Like a spread in a playboy magazine or something.

The rest of that week I couldn’t stop thinking about her and her clothing and on that weekend everything changed forever.

For the 9 years since my dad left, my mom only had one date and it didn’t go well from what she told me. I knew, more or less, what kind of sexual appetite she had and I thought she must’ve been feeling incredibly frustrated. At one point in my childhood, I remember her and my dad having sex almost every night. I remember her being vocal. Moans, dirty talk all that stuff. For it to just stop and not
have another partner for 9 years had to be frustrating.

I had come home from a friends house and it was around 1am. To my surprise my mom was still awake. I could hear her singing in her bedroom. That meant she had been drinking because whenever she sang in the middle of the night, she was drinking. My mom was an alcoholic but most nights was a very depressed alcoholic. For her to be singing, she had to be in a good mood.

“Glad one of us is in a good mood tonight.” I said as I walked up to her door.

“Oh geez you startled me! I didn’t know you were home.” She said taking her headphones off.

She was not nearly as intoxicated as I thought she was. In fact she seemed pretty much normal. She was however, wearing just a pink silk nightgown with thin straps over her shoulders and with her legs crossed on the bed, I could see she her matching pink panties. Her cleavage was hanging out on top and on the sides. Needless to say the pink nightgown was just a tad too small for my moms 42DD breasts.

I however, was a bit intoxicated and had I been sober, none of this would’ve happened because I wouldn’t have had the courage to go through with it.

My mom ushered me in her room and patted the bed with her hand. I sat next to her and we began to chat. She asked how my night was, how things were going at work or with my love life. I told her that I had no love life and I was feeling pretty lonely recently. She gently rubbed my back and I stood up. While staring at her cleavage, I told her I was going to go to bed. She told me to give her a kiss, which I did and I then walked out of the bedroom. I have no idea what made me stop and make this life altering decision. Perhaps it was the alcohol, perhaps it was the years of fantasizing, perhaps I’m just a perverted freak.

“Hey mom, how long’s it been since you’ve had sex?” I boldly asked popping my head back in her room

“Not since your dad.” She said lowering her head a bit. “It’s been almost 10 years now hasn’t it?” She quietly said

“Do you want to have sex?” I asked

“All the time. I may be 52 but it doesn’t mean I don’t have needs.” She answered

“No, I meant, do you want to have sex with me? Like right now.” I bluntly told her

“WHAT?!” She answered lifting her head up and staring me in the eyes. “Are you joking?”

“No. Hear me out on this.. you haven’t had sex in almost 10 years right? It’s been a while for me but obviously not 10 years…”

“No!” She adamantly refused

“Why?” I asked

“Why? Why? You ask? There’s a lot of reasons why.” She said

“I don’t think it’s that bad of an idea. No one would ever find out, I’m certainly not telling anyone. You’re not going to get pregnant. We love each other. What’s the big deal? We’re just helping each other out with a problem.” I explained

“Let’s just say we did that ok, what if we liked it? We can’t keep doing it.” She explained in return

“First of all, I hope we do like it. Second, we can keep doing it, we’re consenting adults, we can do whatever the hell we want. And third, we don’t have to keep doing it if we like it. It can be a one time thing just to help each other feel better or it can be a long thing, or something in between, I don’t know.” I pleaded

“I think you need to go to bed.” She said quietly

I went to my room and did as she suggested. I laid down and tried to fall asleep. About an hour later, I woke up to my bedroom door opening. I saw my mom’s silhouette in the doorway and she approached the bed and sat down next to me.

“Hey, I’m sorry about earlier. I guess I had a little too much to drink.” I said rubbing my eyes

“Ok.” She said after a moment of silence “..ok, we can try it. Just once though. Tomorrow night.“ she said as she stood up and left without letting me respond.

The next day, it felt like she was avoiding me and I was beginning to think I had dreamed that she said yes. However, that night she made a nice meal for us for dinner. When it was done cooking, she went upstairs and changed into something else. She came back downstairs wearing a black dress and black stockings. She had done her hair and makeup as well.

“Wow! Mom, you look amazing! How has it been so long since you had a man?” I asked

“I’ve never put much effort into it I guess.” She answered as she sat down at the table across from me.

We had a nice meal and we talked. Not about anything important or what we were thinking of doing, just small talk. After dinner we watched a movie on the couch together and barely said a word to each other during. Mom stood up to take the dvd out and it it away. As she turned around I was standing next to her and I gave her a big hug and kiss on the cheek.

“Thanks for this mom. I’ve had a really nice night hanging with you.” I said

“Should we go upstairs now?” She asked nervously

“We don’t have to. I understand that it’s weird and if you don’t want to, I certainly understand.” I explained

She grabbed my hand and lead me upstairs. We enter her room and I sat on the edge of the bed.

“I’m going to go get into something more comfortable. If you want to do the same, now’s a good time.” She said as she left the room and went into the bathroom

I excitedly ripped off all my clothes and got under the blankets. My cock was so hard and sticking straight up, rubbing against her soft silk bed sheets. I thought I was going to cum before she even came in the room. I heard the bathroom door open but I couldn’t see her.

“You know, what we’re going to do is unbelievably wrong and if you want out, this is our last chance. There’s no going back from this.” My mom said from out in the hallway still out of sight

“Can I confess something… I’ve wanted to do this for as long as I can remember. I know it’s wrong or weird but I want this.” I explained

“Just so we’re clear. We’re doing this because we’re lonely and we have needs. We’re not lovers and we’re not going to talk about this ever. Got it.” She said

“Got it.” I answered

Mom took a deep breath, and entered the bedroom. She was wearing the same pink nightgown from the night before. Once I got a view, I sat up and my jaw dropped. She quickly switched off the lights and climbed into bed with me.

I immediately snuggled myself right up against her and started with a hug. I helped pull the covers over her and she then draped her leg over my body. I was worried that I’d be the more enthusiastic one but it seemed like she was equally excited. We were both incredibly nervous!

After a minute or so of hugging and my hands running up and down her back and legs, I finally got the courage to go in for a kiss. As our lips touched, she surprised me by slipping her tongue in my mouth. As we made out I could hear little moans coming from the back of her throat echoing.

We continued to make out for a few minutes when I suddenly felt her hand going up my thigh. She grabbed the base of my shaft and I let out a loud moan. The feeling of her soft hand wrapped around my throbbing cock sent a shockwave of ecstasy through my entire body. Immediately my toes curled and my legs stiffened up. I bit my bottom lip to keep from yelling too loud.

“Oh my god I can’t believe how big you are!” She whispered as she began to slide under the covers.

Before I could realize what was happening, I felt her warm mouth and soft tongue wrap around my cock and slide up and down. I got lightheaded for a second as the realization that my fantasy was coming true. Also, she was really good at what she was doing.

I never understood how some girls take that as an insult. I tell you that you’re really good at sucking dick, that’s not insulting. It’s a compliment 100 percent of the time.

It was dark inside the room but there was enough light from the window that I could see her head bobbing up and down and I almost lost it right there. I had to change something or I was gonna cum!

I reached down and pulled her up and we changed positions. I got between her legs and I dove in. As soon as my tongue hit her wet clit she cried out.

“Yes! Yes! Oh god yes! That feels so good!” She screamed

Just seconds later she wrapped her legs around my upper body, clinched her fists full of bedsheets and started screaming. I felt her pussy getting wetter and wetter and she just kept crying out!

“Oh my god! Fuck fuck fuck!!!” She cried

I had given her two orgasms in less than a minute! When she couldn’t take it anymore, she pushed my head away and told me it was too sensitive and I needed to stop for a minute. I have her 10 seconds or so to catch her breath and then, despite her trying to stop me, I began licking her soaking wet pussy again. Despite her best efforts to stop me, she gave up seconds later and again, after a minute or so I had made her cum again, and a forth time shortly thereafter.

Mom reached down and pulled me up to the pillow and laid there silently for a minute trying desperately to catch her breath. Once she had managed her breathing, she sat up and straddled me. She reached down and grabbed my shaft and pressed it against her wet slit. She took another deep breath, similar to the one before she entered the room almost as if she was fine with all the oral stuff but now we were about to break the rules.

As she exhaled, she slowly sat down on my rock hard cock. Her wet pussy swallowed my 8” cock whole and we both let out a loud gasp.

“Oh god it’s been so long since I had a man inside me!” She cried out as she started grinding on me.

It seemed like she was trying to prolong this as much as possible because my tongue made her cum 4 times in less than 5 minutes but she had been riding me for well over 5 minutes now and nothing.

I managed to keep myself occupied by playing and sucking on her tits as they flopped in my face.

“Oh shit! Keep sucking! Smack my ass!” She demanded as her grinding increased

I did as she asked. I kept sucking her stiff nipples and I smacked her ass. The a second and third time as she demanded. Then she let out a loud screech and sat straight up. My eyes were fully adjusted to the light now and I could see her tits bouncing around. She had her arms up in the air and was running her fingers through her hair which amplified her bouncing breasts. She was grinding away and screaming like I had never heard her scream before!

When she finished, she had fallen next to me on the side of the bed once again out of breath.

“Sweet Jesus that was amazing!” She confessed

“I’m glad you liked it.” I said feeling pretty good about myself at that moment.

“God it’s been so long since a man made me feel like that! Thank you!” She babbled

I had reached my limit of how much I could put out before getting my chance. So I sat up and grabbed her hips.

“What are you doing?” She asked sounding confused

“I’m not done yet.” I told her

“Oh, I thought you finished just now. I’m sorry.” She said now being more cooperative and positioning herself on all fours as I was trying to get her to.

I got between her legs and slid my cock back inside her effortlessly as her pussy was still dripping wet. She instantly dropped her face into her pillow and cried out in joy.

“Oh fuck I’m going to cum so hard!” I yelled out after just 20 seconds or so.

“You’re so big and deep inside me!” She moaned

I gave her one last thrust and shot my seed as deep as I could inside her. I held her firmly in place by her hips and my cock pumped spurt after spurt of hot cum inside her wet pussy.

After I pulled out I collapsed on the bed in a mix of exhaustion and absolute pleasure. I thought to myself, if this is the only time this happens, it was well worth it!

“I’m leaking cum all over the place.” Mom said breaking a bout of silence. “I should clean this up.” She added getting out of bed and heading to the bathroom.

I spent the night in her bed that night as we slept naked next to each other. The following morning I was worried it’d be awkward but it wasn’t. She had woken up before me and showered. I showered and came downstairs to see her relaxing on the couch reading a magazine. She stood up and gave me a quick kiss on the lips and asked if I was hungry.

We didn’t speak of this much after and only had sex one other time about a week later. Not long after that, we gave each other oral one night and then never again. She began to date men afterwards and honestly that made me happy to see her getting out there and meeting some guys. Also, it gave me the chance to get out there and meet some people. Also also, it gave me a chance to listen to her and her dates having sex in the next room.

Maybe most guys would be horrified by strange men having sex with their moms but not me. Yep, I’m fucking weird as shit.

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