Just Give It a TrybyRoscoe28©
All characters are over the age of 18 in this story.
"Dude, I discovered something awesome last week. You're going to love this one," said Derrick.
"I doubt that I would," I said.
We were jogging in the local park for the last 20 minutes, bullshitting about various stuff like sports, music, college and of course girls. Most of the time it the things we talk about are ok, but then there are times when he just disgusts me with some new sexual fetish that he's experimenting with. It has come to the point where I knew when it was coming and braced myself for what I'm about to hear. A normal person would just walk away, but he was my friend so I just shut up and listen.
"No, dude, seriously, this is a good one. Let's take a break and I'll tell you all about it."
We stopped at a bench that had a water fountain next to it. We each drank some water and sat down. After we caught our breaths from the jog he began to tell me what you he was so excited to tell me.
"Ok, dude, brace yourself," he said.
"When you say things like that, it makes me want to run away," I said.
"Just hear me out, you might enjoy this yourself," he said. "Every day for the last week I've been jerking off to the image of my mom."
"Goodbye," I said and got off the bench. But he grabbed me by the arm and pulled me back down.
"Dude, hear me out ok. I know it sounds gross, I thought so also when I first tried it. But dude, I got a huge hard on and orgasm each time I tried it."
"Goodbye," I said again. Again I tried to get of the bench but he pulled me back down.
"Dude, it's not as bad as you think," he said.
"Yes it is, Derrick, you're talking about jerking it to your Mom. That's sick."
"Yeah, but she's hot. Come on, you think so too, don't you?"
"Yeah, I think she's hot, but she's not my Mom."
"Dude listen to me," he began to say. "I know its wrong, but that's what makes it so exciting. The fact that it's so... well, taboo is the right word for it... that it makes the whole experience so exciting. You should try it too."
"Hell No!" I shouted at him.
"Listen, dude, we each have been blessed with a hot Mom. It's like God gave us our own personal eye candy for us to look at for the rest of our lives. Or at least until we move out of our own houses. Just give it a try."
"Derrick, I'm not even going to dignify any of this by listening to any more, let's just finish this jog."
He agreed to change the subject as we finished our jog. After that we mostly talked about sports.
When I got home I was in desperate need of a shower. In the upstairs hallway on my way to the bathroom I ran into my mother who had just gotten out of the shower herself. Her hair was still wet and slicked back and she had a bath towel wrapped around her body with some cleavage showing on top.
"Hello Kyle," she said as she walked passed me to her room. "The shower is all yours."
I got undressed quickly and jumped into the shower. In there I couldn't help thinking of how I just saw my mother in that bath towel. Maybe it was because of that conversation I had with Derrick earlier that it got into my head and made me look at her differently. But he was right about one thing, she was very attractive for a woman of 40. She used to be a model when she was younger, first doing those back to school ads when she was a teenager. But then after she turned 18 and graduated high school she went into more risqué stuff like bikinis and underwear ads, more specifically lingerie. She retired early when she met my father, got married, had me and decided to be a stay at home wife and mother.
Of course that didn't last long when my dad kept cheating on her she filed for divorce. She got enough in the divorce settlement to open up a ladies gym and stayed fit and healthy by being one of the gym's aerobics instructors. Derrick wasn't the only one of my friends to find her attractive; a lot of my other friends teased me about it. She had long dark hair, a slim body, a shapely ass and perfect 34D tits.
Thinking about my mother's tits started to give me a chubby in the shower so I quickly turned my thoughts to baseball and finished the shower with no more dirty thoughts. I got out of the shower, dried up and put a towel around my waist before I left the bathroom.
"Mom, is the laundry done?" I called out.
Nobody answered. I went to my room and looked at the window to the driveway. Her car wasn't there; she probably went back to work. I found a laundry basket on my bedroom floor, it turned out I didn't even need to ask. I went through the basket to look for a new pair of boxers when I found at the bottom a red lacy bra that she must've accidentally dropped in there. Instantly the thought of my mothers' tits gave me anther chubby. I put the bra back into the bottom of the basket and tried to think of something else, but I couldn't help myself. I took off my towel and saw that I had a wicked huge hard-on; I haven't had one like that in a long time.
"Well," I said to myself. "It couldn't hurt to just give it a try."
So I decided to give it a shot, just as an experiment to see what it would be like. But I wasn't going to bring out that bra again. I went online to my computer and pulled up an old modeling photo of hers that she had on her facebook photo page. I got one of her last photos she took before she retired. It was one that had her in a red skimpy bikini; she had just gotten out of the pool and was looking at the camera with a sexy smile.
I began stroking my dick good and hard. I never got so excited to jerk off so hard like this before. I can't believe I was going to say this, but Derrick was right for once. It was exciting; I was pounding my meat as fast as my heart was pounding in my chest. I still knew it was wrong but it only made the whole thing more exciting. I thought about her in different sexual positions and then I imagined her taking off her bikini top and begging me to feel her tits. After about 15 minutes of jerking off I felt that sensation in my balls that told me I was about to cum. I opened one of my desk drawers, pulled out some tissues from a box I had in there and prepared myself. I shot one of the biggest loads of jizz I ever had into those tissues. After it was all over I threw the tissues into the waste basket and sat back in my chair.
"Wow," I said. "That was intense."
"I'll bet it was," said a voice behind me.
I jumped out of my chair and covered my dick with both hands as I saw my mother standing in my doorway. Her eyes and mouth were wide open in shock from the fact that she had just witnessed her only son jerking off to an old bikini photo of hers.
"I forgot my cell phone," she said.
"Mom, please, I can explain! Oh, please let me explain!"
"First get dressed, and then meet me in the living room."
She left and went downstairs. I quickly got dressed but it took me a while to leave my room. I was scared of what was going to happen. I went through a thousand conversations in my head on how I was going to explain this. I knew one of the main things I had to do was to blame this all on Derrick.
I went downstairs to the living room and found her sitting on the couch. Before she said anything I quickly went through the whole detail of what Derrick told me. Blaming his perversions on how it was affecting my mind and that it was only an experiment and I felt very, very guilty about it. I was talking fast and panting while walking back and forth in the living room, begging her to forgive me for what I just did.
"I will never do it again," I said. "I swear it, never, never, never again. I didn't even enjoy it"
My mother laughed at that last comment. "Oh, please, don't lie."
"No, it's true," I said.
"Honey, I just saw you. You were really enjoying yourself, especially when you finished it off you had a big smile on your face. Now don't you lie to me and at least admit you liked it."
I sat down on the chair that was across from her and took a deep breath.
"Ok, I admit it. I did enjoy it. I knew it was wrong but it felt really good nonetheless.
"Kyle, its ok," she said. "I believe you. This was just a one time mistake."
"Yes, I do," she assured me.
"You seem really calm about all of this. Why is that?" I asked.
'To be honest, I was shocked at first, but now I'm kind of flattered."
"You are?" I asked with much surprise.
"I know it sounds strange, but it's kind of flattering to be desired like that, even by my own son. I still think it was wrong, but I just can't help being flattered by the whole thing."
"So we're good then?"
"Yes we are," she said.
She stood up from the couch and walked up to me. She bent down and gave me a kiss on the cheek. I knew I shouldn't be doing it but I couldn't help looking down her shirt when she kissed my cheek. She said she had to go back to work and left leaving me wondering what I should do now. Eventually I decided to go upstairs, get of my playboys and jerk off to a photo of a big breasted blonde.
The next day I was hanging out with Derrick at his place watching a baseball game. His mother wasn't home so he felt it was ok to continue the conversation we had yesterday with some extra details.
"Last night I jerked off to my mom while she was fucking one of her boyfriends," he said.
"Why am I friends with you?" I asked.
"Her door was slightly open; she didn't even know I came home early. She was on top of her boyfriend riding him hard. I only saw her from the back but I can see the sides of her big tits bouncing around. So I dropped my pants and began pounding my meat and—"
"Please, stop," I interrupted. "I want to watch the game."
Really, I wanted to forget about what happened to me yesterday.
"I'm telling you dude, you should try it," he said.
"Not going to happen," I said.
There was no way I was going to tell him that I already tried it and the result of the situation. I still couldn't believe that my mother forgave me so easily.
I got back home a few hours later and found my mom in the kitchen drinking coffee and looking at her old modeling portfolio. I got a soda can from the fridge and sat across from her.
"What are you up to?" I asked.
"I was just looking through my old photos," she said and then looked up at me and smiled. "I was inspired to look through them again."
"Oh, jeez," I said and took a sip of my soda.
She laughed as she turned the page in her portfolio and pulled out the photo I had of her yesterday.
"Remember this one?" she asked and laughed.
"You're having fun with this aren't you?"
"Of course," she said. "Listen, can I ask you a personal question?"
"Ok," I said.
"It's about what happened yesterday."
"Dammit," I said and sighed. "Ok, ask me."
"That was an old photo of me from when I was much younger. Would you have done the same thing with a present photo of me?"
"Oh, jeez," I said.
"Please, I have to know. I haven't been feeling all that attractive lately, haven't been out with a guy in a long time. I need to know this.
I took a deep breath and looked her straight in the eye.
"Mom, you're very attractive. In fact, you're hot," I took another deep breath. "If I had a present photo of you in a bikini, I still would've done the same thing."
"Thank you honey," she said with a big smile. "That really made my day."
The next day I was hanging out with Derrick again. I tried to keep the subject on sports or music but he just went on and on about how he spied on his mother in the shower and jerked off to her again.
"Dude, you need to get a real girlfriend," I said.
"Listen, dude, it's just for fun. Hell, she probably knows I do it. She may even like to watch me, or even fuck me."
"Oh, jeez," I said. "I doubt that."
"Why not? She's kind of a slut anyway, that's what her third husband says."
Derrick's mother married a man who only used her as a trophy wife. In fact that what was implied in their prenuptial agreement; that this wasn't about love, but to have a hot woman on his arm. Seriously, that's what it said, Derrick showed me a copy. The prenuptial agreement also stated that they could still sleep around on each other as long as she kept it quietly and maintained her figure, and get breast implants. It also said that the marriage would end when she turned 35 so he could marry another young trophy wife. It was ok with her because she got a house and huge cash payout from the marriage. It was an undisclosed amount, as part of the agreement, but it was enough that she never had to work again.
"Dude, I'm telling you, you should try this," he said.
"I'll pass," I said.
I got back home a few hours later. My mom rushed outside the door, she was in a hurry to get back to work. But she stopped just quick enough to give me a kiss on the cheek before she left. When she kissed me she leaned in close enough that her breasts pressed up against me and I felt a stir in my pants. Again I pushed it out of my mind and went upstairs to get out my porno to distract my mind with other girls who weren't my mother.
On my way to my room I had to walk past my mother's bedroom and I looked inside. On her bed was her old modeling portfolio with some of the photos tossed around the bed. I assumed they were there because she was still obsessing over the past. I walked into the bedroom to take a closer look and saw that many of the photos were from her old lingerie ads. Looking at them got me hard real fast.
"Oh, the hell with it," I said and picked up one of the photos. "Just one last time."
I took the photo to my room and propped it up on my desk. This picture had her standing wearing a black lacy bra with matching panties. I took all my clothes off and sat down in my chair. My dick was hard like a steel rod; I grabbed my dick and stroked it fast and hard. I got the same satisfaction that I got from the first time. I imagined my mother dancing for me and getting naked. I thought of her taking my dick in her hands and stroking it for me and putting it in her mouth.
"Now that is something," said a female voice behind me.
Like before I jumped up from my chair and covered my dick with both hands.
"Mom!" I yelled. "I am so sorr—"
I stopped talking and let my draw drop as I saw my mother standing in my doorway wearing pretty much the same thing from the photo.
"I knew you couldn't resist yourself," she said with a wicked smile and then walked into the room. "I told you I was flattered, didn't I? Now please continue."
I didn't say anything it was like I was in a trance. I sat back down in my chair and resumed stroking my dick. My mother started dancing around for me; she was shaking her hips, rubbing her body with her hands, licking her lips. I couldn't believe what was happening. This was even more exciting than sneaking behind her back to jerk off to her body because having her part if it was even more taboo which made the sensation even more intense.
She took off her bra, her tits were better than I imagined them to be. She dropped her panties, her pussy was shaved and I can her starting to get a little wet. She got close to me and I reached up with my free hand and grabbed one of her tits. I never felt tits like that on any other girl I've been with. She bent down and gave me a gentle kiss on the mouth, and then she opened her mouth and slipped her tongue into my mouth. I let go of my dick and put my arms around her to bring her close; our bodies pressed against each other as we locked in a passionate kiss. She broke that kiss and began sliding downwards on my body until she was on her knees and her head was between my legs. She opened her mouth wide and took my dick into her mouth. She sealed her lips firmly around the shaft and began bobbing her head up and down. She moaned as she sucked it hard and deep. I grabbed the back of her hair and gently pulled on it a little, she seemed to like that. She deep throated me a few times, gagging each time.
I pulled her head from my dick and got her to her feet. I took her by her hands and pulled her out of my bedroom and into hers. I wanted to fuck her but I wanted to do it on a bigger and better bed than mine. I threw the modeling photos that were still on the mattress onto the floor and tossed my mother on the bed. I jumped on top of her and began kissing her lips again. We rolled around on the bed for a few minutes kissing then I moved down to her breasts on her fully erect nipples.
I had her on her back, her legs were spread open. I took my dick and guided it right into her pussy. She yelped from the pain as I put myself inside her body; her pussy was wet but tight, she hadn't had a good size dick in her for a long time. Usually I take it slow because with a girl but this time I didn't even bother with that and just went as hard and fast as I could and despite the pain she definitely didn't mind. She began breathing heavily and her eyes are closed. She began to shake as an orgasm coursed through her body. I grabbed her by the hair and pulled her to my lips as he gave her a good hard kiss.
We rolled over and she was on top of me now. Her hands were firmly placed on the head bard as she began to grind her hips around my cock as I in turn pushed myself upwards for good measure. Her moans grew louder as I had one hand tightly squeezing her left ass-cheek and the other hand on her right breast. I gave her ass a few good hard spanks which she loved and asked for more, which I did.
I got her on her back again and I grabbed her hands and held them firmly over her head. I forced myself to push harder into her and faster, I never felt this way before. She moaned wildly, both in pain and in passion, and before she knew it another orgasm shot through her body as she let out an ear-piercing scream of ecstasy. I kept going for several more minutes like this, trying to make this last longer than it should, but eventually I couldn't hold back that much longer. I pulled my dick out of her and prepared to cum on her body. She then told me that she was on the pill and begged me to put it back in and cum inside of her. I put it back into her pussy, pumped my dick in her a few more times before I shot my entire load into her body.
Afterwards I pulled out of her and lay down next to her. She moved over to me and put her head on my shoulder as I put my arm around her.
"That was fantastic," she said.
Over the next week made love several more times before we decided to settle it down and make some rules. We knew it wouldn't last forever and we needed to see other people so we had to take it slow. We agreed to have sex no more than twice a week, with extras on birthdays or special occasions.
Two weeks later I ran into Derrick on campus and he looked really upset.
"My mom kicked me out of the house," he said. "She caught me jerking off to a photo of her."
"Wow, sorry to here that," I said sympathetically.
"She probably would've forgiven me and let me stay if I didn't suggest that we fuck each other. That's when she lost it and kicked me out and she cut off my allowance."
He went on to say how he was staying at another friends house and his mother agreed to let him back into her house after he sees a therapist for about six months which she would pay for. Also, he had to get himself a job and raise his college GPA.
"Dude, forget about what I told you before," he said. "Don't jerk off to your mother, its not worth the consequences."
"I totally agree," I said trying to hold back a smile.
"My mother is an evil slut and she threw me out of the house. You're mother is sweet, who knows what she would do to you."
I told him I had to go finish a term paper, when really I went back home to fuck my mom again.