My Midlife Awakening Pt. 01

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My Midlife Crisis with Stepson.
1.8k words
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Part 1 of the 4 part series

Updated 06/11/2023
Created 07/08/2022
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My name is Lesley and I am in my mid 40's I have had quite an experience over the last 5 years or as I like to say my midlife crisis.

A little background about myself before I begin my story, at the time my so-called midlife crisis starts I was divorced and married to Bob who had a son named Steven. I came from money and my first husband was well off so when we divorced I was taken care of, and Bob also did very well for himself. So I did not work but did a lot of volunteer work and charity work to make up for it.

As for sex well, I grew up with strict parents so never had that fun or the fun college life. My 1st husband was very boring in that department, and Bob was better but a once-a-week missionary person, with little to no foreplay.

I am in decent shape I am 5'5 and weigh about 120, with 34b. I hit the gym 3 to 4 times a week and have a personal trainer to maintain my diet and exercise.

That's enough of my background now on to my story.

Bob and I have been married for about four years, and as I look back at it now it was a mistake marriage. I jumped into it fast after my divorce as I was not used to being alone, Bob was older by about 10 years and was very into his work and I think got married so he wasn't alone either. His son Steven would only stay with us part-time on weekends and he was no trouble at all, and I did my best. But as I approached 40 or as I said above my mid-life crisis I had a sexual awaking in myself.

Around this time I also met Jodi thru the volunteer work I was doing, she was also a helper, she was around my age divorced for many years, and single and loving life. Jodi and I became fast friends at first having lunches together and eventually shopping and going to each other's houses. Jodi talked a lot about her sex life something new to me but helped me crave something I never felt before.

I started to think about sex a lot, and discovered porn and sex stories online, causing me to spend a lot of time masturbating, making up for a lot of lost time, and also leading to toys I purchased. I tried to push Bob to have sex more but it never worked it was just not him.

Around this time Steven moved into our house after he graduated, his mother moved away, he was now 18 and planned to stay with us for summer and was going to go to community college to get credits until he decided where he wanted to go.

Steven turned into a very mature 18-year-old, but it was not hard to notice him glancing at me when he thought I was not looking, and I must admit I loved the attention since my husband was not giving me any. One night we were watching a movie sitting on a couch, and a sex scene came on the screen, it was nothing serious but somewhat erotic, and I noticed a bulge in Steven's shorts. I was in shock but at the same time it excited me and made me wet, I believe he noticed me looking and tried to cover it up. Bob was traveling which he does a lot, so after the movie, I went straight to my room where I masturbated with thoughts of Steven. Afterward, I couldn't believe I thought of him doing that, but after a while and getting horny again I thought of him again.

Thoughts of him kept going thru my brain, I even started to look up stepmother porn and stores driving myself crazy, along with checking him out around the house. But it wasn't until I spied on him that drove me even more crazy. About 2 weeks after the movie incident and driving myself crazy thinking of him every day I went into his room when he wasn't home and looked on his iPad, and in his history, I found that he was watching stepmother porn. Right there on his bed, I fingered myself, yes on his bed watching the porn he was watching.

After finding that my mind went into overdrive with wanting to be with him, wanting to make a move already. It was the following week when Bob was traveling and got myself nice and horny all day, and planned for a movie again. We were on the couch watching and I piked something that I knew had a sex scene, nothing hardcore but enough to turn him on like the previous time. And just like last time when the scene came on I noticed his bulge, he saw me look at it, and then I looked at him in his eyes without saying anything. Then without thinking I put my hand on his shorts over his dick, making him moan. We just looked at each other until I pulled his shorts down a little and grabbed his hard dick with my bare hand jerking it a couple of times until he shot cum all over the place. I kept jerking looking at him, I wanted more but started to feel guilty and could tell he was embarrassed. I just got up and left and went to my room.

Once in my room I felt very guilty and couldn't believe what I did, yes he was 18 but it was wrong. I took a shower and then lay in bed but after a bit, my mind returned to thoughts of Steven and what I did on the couch, and before I knew it my fingers were buried in my pussy deep moaning. So it was a shock when I heard him call out my name and I opened my eyes to see Steven looking at me masturbating in my bed. I stopped by didn't say anything and looked at him with my fingers still in me. It's then I noticed he was naked as he got into the bed, I removed my fingers and it was replaced with his dick sliding into me. He went fast and came quickly again, coming inside me, as I also came wrapping my legs around him tight as we screamed in joy together. We held each other for a couple of minutes until he got up and left for the night, I never even got up to clean up as I fell asleep with a smile.

I awoke the next morning feeling guilty, embarrassed, and not sure where we go from here, Bob was away for another day, and Steven was already out of the house as he was working part-time. Right before he came home I decided to go out as I didn't want to be home when he got home. When I returned home I saw his car, and as I walked into the house I became very nervous, what would I say, what would he say, as I was in the kitchen I quickly found out how he felt. Steven walked into the kitchen and I said hi and tried to play it cool, but he came up behind me hugging me from behind and trying to kiss my neck. I said we can't do this but at the same time, didn't push him away or even say no. He started to kiss my neck and rub my body as I became instantly wet, he then pulled my head back as our mouths met for the first time and we kissed with passion.

Any guilt or wrong thoughts were gone from my head and I was only thinking with passion at this point as we were kissing and rubbing all over. This was new for me and never felt like this before, so I did was I have seen in videos and read about in stories, and fell to my knees, pulling his shorts down and pulling his cock out. I tried to suck Bob once which lasted seconds until I stopped, he was not into I was not into it, but I was so into this now. I took Steven's cock and did the best I could for this real first time, sucking his cock, licking his balls. After about 2 minutes he yelled he was going to cum and I did my best to swallow with the majority spilling out of my mouth. Tasting it for the first time was not bad and I cleaned his dick off driving him nuts as he stayed hard.

I then got up and grabbed his hand as we headed to the bedroom, and once in there I stripped off my clothes and laid down and asked him to eat me. I never received oral before so I had nothing to compare so at that time it was amazing, I look back now and I give him credit for trying but this was his first time so he didn't know what he was really doing. After a couple of minutes, I asked him to fuck me which he did and he was able to last longer but still shot quickly. But once he came he stayed with me in the bed as we fooled around performing oral and having sex all night long in bed and in the shower.

This affair would go on for a couple of months at first we had no clue what we were really doing but we got better at it and had the most amazing sex. When Bob traveled we fucked all over the house, and when Bob was home we would sneak around once Bob went to bed or before he came home.

One day out of the blue Bob confronted me about the affair, he had suspicions and he confronted Steven who told him the truth. Bob was furious and who can blame him but was more concerned with people finding out and protecting his image with work. He told me that he sent Steven away and he was moving away to where he has been traveling for work, I can have the house if I agreed to never talk about this and sign papers around it and never contact them again. I was hurt I had feelings for Steven but also knew they wouldn't go anywhere and agreed.

Bob made the divorce happen quickly and just like that at the age of 41, I was divorced for the 2nd time. But I felt different this time freer, a new sexually feeling was woken inside me that I had to experiment with now.

My story continues as I hang with Jodi, and also get a new boy toy.

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4 Comments
cumslowlycumslowlyalmost 2 years ago

The story is much like many others. Try to make your stories unusual. something out of the ordinary. I hope it was based on your own experience. That always makes it exciting.

AnonymousAnonymousalmost 2 years ago

Good story for a first time. It felt rushed, especially the first two times with Steven. I do look forward to reading more

AnonymousAnonymousalmost 2 years ago

It’s a very good story, and believable if not true. I would have loved it to have been a bit slower, with more details about both the individuals worked into it (physical descriptions, etc.) and the acts that they participated in. Please keep writing!

AnonymousAnonymousalmost 2 years ago

Good for you. Life is short!

HAVE FUN WHILE YOU STILL CAN!

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