I have always heard that it is socially unacceptable to date someone less than half your age. Well, I have never really concerned myself with society in general. In my opinion, people can either deal with me or fuck all the way off. I did not ask their opinion; nor did I want one either. That has always been my way of living life. I take what life gives me and I really don’t care what people think.
So, I guess some background would be good. My name is Jeff. I was married to the love of my life, Abigail, for over 27 years. We raised two children, who now have families of their own. Unfortunately, our time together had an expiration date on it. Five years ago, my wife died after a year long battle with liver cancer. I helped her as much as possible. In the end, I had to do everything for her. And, I held her hand as she left this world. I swore I would never seek out or attempt to replace her in my life. However, fate decided otherwise for me. This is that story.
I work evenings at huge hospital. I have worked here for the last 25 years. The job itself sucks. But, it’s a paycheck and I like my co-workers. So, I have dealt with the never ending flow of shit that management seems to send our way almost monthly. The one thing I have never liked about my fellow co-workers is how they treat our janitor staff. The only time they even talk to them is when they need something cleaned, picked up, or thrown away. Me, on the other hand, I have gotten to know each and every janitor that has ever worked at my job.
Over the last 9 months, our janitor has been this sweet, 19 year old named Jena. Jena looks like she could be Zendaya’s little sister. Same skin tone, same body type, same hair color and style hair with smallish boobs. Over the last nine months, I learned that she had moved out of a very toxic home life during her 11th grade year in high school. Although she got her GED, she has confessed that it has been a real challenge to find a good paying job. Jena lives with her boyfriend, who is two years older. They live in a small, one bedroom apartment; which she calls the “Shithole”. Also, her boyfriend is a drug dealer and a real piece of shit at times, according to Jena. But, she stays with him because she had literally no where else to go.
I had not seen Jena in over a week. Then, the following week, she showed up. Jena was about to start her rounds when I noticed that she had been crying. Eyes were all red and her checks were streaked with tears. I asked her what was wrong, but she couldn’t even get the words out without crying. So, I took her to the old equipment room. Once she was calmed down enough to talk, Jena told me that her boyfriend had gotten himself thrown in jail and was going to prison for distribution of heroin. She also got evicted from her apartment because of her boyfriend dealing drugs out of the apartment. So, she was now living in her car.
After another couple of breakdowns, Jena said she didn’t know what she was going to do. She had no where to go. Now, I don’t know if I felt sorry for her, or just wanted to help. But, I told Jena she could live with me until she had saved up a good amount of money. She perked right up at this point. “Jena, I live alone and have two extra bedrooms. You can help out in whatever way you can. All I ask is no visitors. I like my solitude. How does that sound?” Jena hugged me, kissed me, and hugged me again.
After work, Jena followed me home from work. I showed her the room she could use, the bathroom and the kitchen. She thanked me again and headed straight for the shower. I cranked up the hot tub and outdoor sound system. Poured myself my usual and jumped in to relax. Almost 30 minutes later, Jena came out wearing a towel wrapped around her small frame. Jena asked me if she could join me? I told her to grab a drink if she wanted. She pulled out a beer from the backyard frig, dropped her towel and got into the hot tub butt ass naked.
She proceeded to sit right next to me. “Jena, staying here has no conditions attached to it. You don’t owe me anything.” Jena reached up my swim trunks and grabbed my cock. It immediately started to get hard. “Jeff, that is exactly why I want to. You didn’t put any restrictions on me staying here. You did it because you are a kind and caring person. So, if you want me to stop, I will. I can’t pay you much. But, I can love you if you will let me.”
I didn’t know what to say. Jena was so beautiful; but, she was younger than my youngest daughter. That really didn’t matter at the moment. My body was responding to her touch. My heart beat was going a mile a minute. With nothing to say, Jena took that as an affirmative and leaned up to kiss me. It was my first kiss since my wife had past away. Jena pretty much took over at this point. As our tongues danced, she pushed my swimsuit down and off. Then, she mounted my lap, reached down between us, and guided my cock up inside her pussy. It had been well over seven years since I had last had sex; which I told Jena. She went slow; but kept kissing me the entire time. Her warm pussy enveloped me. It was pure heaven and she was my angel.
Within just a few minutes, I warned Jena I was about to cum. I thought she would stop. Not only did she not stop; she increased her bouncing up and down my cock. “Holy Christ” I yelled out as my cock let loose with rope after rope of cum up inside this young girl. Jena continued to bounce up and down thru my entire orgasm. With my cock still buried up inside her, she bent down and whispered, “How about you show me your room.” I grabbed both sides of her ass with my two hands and stood up; keeping her impaled on my still hard cock. I walked us into the house, thru the living room and straight to my bedroom.
Thoughts of my wife shot thru my head as I gently laid Jena on her back. Jena continued to kiss me the entire time. Since I was still fully erect, I started to fuck her pussy with my old cock. If it bothered Jena, she most definitely did not show it. She was moaning out loud and had wrapped both her legs around my body; pushing me deeper inside her. After Jena had her first orgasm, so rolled us over on the bed as I was now on my back.
Jena had an amazing body. Like I said, she could have been Zendaya’s little sister. Jena really started to bounce up and down hard now. She was clearly fucking herself on my cock. This went on for several minutes. Then, she reached down and pulled both my hands to her tits. Using my fingers, she pinched and pulled her nipples as her next orgasm started. Then, she screamed out loud that she was cumming. I continued to alternate between pinching and pulling her nipples as she rode me thru another big orgasm. Since I had already cum once, I knew it would be awhile before I came again.
Jena got off me and laid down beside me on the bed. She saw the pictures of my wife and asked me all about her. So, I got to talk to someone about my favorite subject. I went thru our entire history from high school all the way to her last days. Afterwards, Jena looked at me and said, “Do you think she would be ok with this? With me bringing you pleasure and vise versa?” I paused a moment before answering. “Yes, I think she would. She was very open minded and told me not to give up on love if I ever found it again.” Jena smiled at me and kissed me.
“Good. Then, do you think you could fuck my ass? I love anal sex. But, the boyfriend took so many drugs that he could never get hard enough to get it inside me.” I looked at her and replied, “With a little help, I could very well try.” Jena immediately bent down and took my semi erect cock into her mouth. Using her talented tongue, mouth and hand, she had me hard enough to hammer nails into a wooden board. I turned her over on her knees and lubed up us both with some KY I had in the bathroom.
I pushed my cock thru her sphincter muscle with ease. Then, with just a few pushes, I had her beautiful ass up against my pubic bone. “Jesus Christ. That feels so good. Please don’t stop until you fill my ass up with your cum.” I grabbed both her hips and started to hammer in and out of her ass. Jena started to moan out loud right away. Within a couple minutes, she had another screaming orgasm. After five more minutes, she was speaking in tongues. Once I felt that my orgasm about to hit, I rammed my cock as far inside Jena’s ass as I could and released everything I had in my balls. My whole body felt like it was convulsing.
Once I was finished, I pulled out and excused myself to go clean up in the shower. Once in the hot water, Jena joined me and we took extra time to help each other get clean. I dried myself off and headed over to the bed. This old man needed sleep. I figured Jena would go back to her room. But, she crawled up into bed with me and we both fell fast asleep; enjoying the feel of a naked body against mine for the first time in seven long years.
The next morning, I was woken by a warm, wet mouth on my cock. Once Jena realized I was awake, she leaned up said smiled at me. She had made breakfast and coffee thinking I needing to refuel after last night. I told her “Thank you. But, I seem to have an erection problem. Do you have any idea how to fix this?” Jena smiled at me and returned to sucking my cock. And this time, she had me cumming in less than 60 seconds. She was very, very good at sucking cock.
We ended up talking more at breakfast. Jena asked if I had enjoyed last night? I think my smile was more than enough of an answer for her. Then she said, ” Jeff, you can have me any time you want while we are here at the house. Any time, any place and in any hole.” I laughed as the images raced thru my head. “Jena, your conditions sound more than generous. However, keep in mind I am in my 50’s. That will not be an every night thing.” Jena giggled and got up to get more coffee. “Give me enough time, I bet we can have you up to at least three times a week before too long.” See blew a kiss my way and disappeared. I just shook my head and thought, “Jesus Christ. What have I gotten myself into?”
Jena ended up staying almost 2 years. She introduced me to threesomes, partner swaps, sex clubs and all kinds of kink. But, I will say, I was in great shape by the time Jena moved on. And the last time she called me, she now had her nursing degree.