Grad Student & Mature Neighbor Bond

Background:

This story is a look back at one of my fondest memories/experiences from my college years. The majority of the story is true, with some of that truth being stretched. This is also my first story so please be kind, yet critical in your responses. I had a difficult time choosing a topic for my first story. I want to know if I should continue with this series/plot/characters or if I should branch out. I have plenty of experiences, as well as fantasies to write about.

Story:

I took an extra year of undergrad and I was about to turn 24 when I began grad school. After graduating from a college close to home, I chose a program at a different college out of state, where I could have a bit of freedom to do my own thing. It was also the only college that offered me a job as a graduate assistant baseball coach for their team. I had played for three years in my undergrad and wanted to be on a coaching staff somewhere.

I found a fully furnished apartment to live in about 3 miles from campus. I signed a one year lease even though my graduate program would last two years. I felt that I'd maximize my time in a new area by finding a new apartment for year number two.

My neighbors were friendly, but I noticed that most were not around my age. Many were young couples with kids or dogs, but there were also a number of older, retirement aged people living nearby. So I only interacted with a quick "hello" or greeting of some sort.

I didn't meet many people in my first week or two living there... I was busy on campus preparing for classes and meeting with the coaching staff as we prepared for the fall season. As practices began, I became even busier. Luckily the fall season only lasted 4 weeks and I'd have more free time after that. Though I enjoyed it, the days were long and my personal time was at a minimum.

One Saturday evening, I returned to my apartment around 5:30 PM after a day full of practice/games. I parked a few houses down from my apartment and reached in the back seat for a pizza box. I felt too tired to cook so this seemed like an easier route. As I stepped out of the car in my uniform (baseball hat, pants, team shirt), I noticed my neighbor sitting on her porch relaxing in the sun. She lived two doors down and looked to be similar in age to my parents at the time. My guess was she was in her mid-fifties. Though she was older, she was quite pretty and I had noticed her a few times in the previous weeks. She was a shorter woman, probably about 5 feet 4 inches, with naturally curly auburn colored hair. Her curves were delightful. A thicker mom build with large breasts and a round bottom. Definitely not immune to thick thighs and a cute belly.

In my first week at the new apartment, she was working in her garden and I was drawn to her ass in her tight yoga pants. I thought to myself "I've been around a lot of college girls this week but this lady might have one of the nicest ass I've seen." After that moment, she continued to catch my eye. My cravings for mature women, which were not new, only increased.

I had yet to meet her and did not want to be rude as I passed by. Unsure of what to say, I commented on the weather and how nice the sun had felt that day. She smiled and noticing my uniform, continued the conversation saying "what a great day for baseball", before adding in "I always thought those uniforms looked great. A handsome young man like you only confirms my thoughts" with a sly yet confident smile.

My heart was racing. The comment was innocent enough, but it also carried with it a fair amount of sexual tension. Perhaps it was just me and my cravings that caused me to feel this way. Again, not sure how to respond, I decided to play the sympathy card.

I said "If only the college girls I have classes with felt the same way!" with a laugh. Her face turned from a smile to a bit more serious when she responded and said "they don't know what they're missing out on! Don't waste too much time on them honey."

I smiled and there was an awkward pause as we both gave each other a good look over. Finally the silence was broken when she said "by the way, I'm Darlene. I've lived in this neighborhood for years. Don't hesitate to knock on my door if you need something." With that, she began to get up and walk toward the door. I took this as a last chance to size her up. Her butt seemed to jiggle as she moved and her tits seemed larger than I had previously thought based on the tighter shirt she was wearing.

I took this as my indication to finish walking to my place. As I started toward my apartment I responded by saying "Darlene, my name is John. You are very kind and I hope to see you around!"

Moments later I reached my front steps and entered my apartment. It was dark and quiet. I was hungry, tired, sweaty, and now horny from my conversation with my sexy older neighbor. In my mind, I debated what to do first - eat a slice of pizza, take a shower, or hunt for some MILF porn to watch. I chose to quickly eat a slice before heading to my room.

In my room I have a personal laptop and a television mounted onto the wall. I use the laptop to stream sports and shows up to my TV so I don't have to pay for cable. I also use it to stream porn onto my TV and that was the plan for tonight.

I propped up the pillows on my bed and sat there rubbing myself through my baseball pants as I searched for videos of mature women fucking younger men. After finding one, I pulled out my hard cock and balls and began stroking. The musky scent from my compression shorts and sweating all day only made me feel even more horny. As I stroked my cock and watched a mature milf suck on a younger guys big cock, my mind continued to wander to my neighbor. I really tried hard to imagine the characters in the video as Darlene and myself.

Whenever I masturbate, I like to take my time. It feels so good that I don't want to stop. I like to tease myself and prolong the enjoyment. After about twenty minutes of stroking to this video and fantasizing about Darlene, I decided to take a short break.

I was in the mood for some dirty talk to increase the enjoyment during my stroking session. In the past, I had used dating sites like Tinder to find dirty minded girls/women to chat with. I had been so busy in recent weeks that I hadn't been on Tinder since moving. I decided to check it out.

When I opened the app, the first thing I did was check out the profiles of a few previous "friends." These were mostly girls I had matched with or met in college. I sent a couple messages but didn't have much luck. I decided to check out some local profiles to see if I could find a new match.... I was interested in both someone to talk dirty with and/or someone to meet and hook up with or even seeing where things take us! But communication and getting to know each other was important. Especially sexually. I have many desires, kinks, maybe even fetishes. But I get off on mutual enjoyment and providing pleasure as well.

After a bit of scrolling and swiping, I put another MILF video up on the screen. And then it dawned on me... I could adjust the age range on Tinder. I changed it so that I was looking at women ages 35-60. It was always set at 21-30 but I was curious and figured there was no harm. I was in a new area and the fear of revealing my identity to a friend of my parents or older sibling no longer existed.

Between scrolling for older women on Tinder and watching MILF porn on my big screen TV, my cock was pulsating and my balls were begging for release. At this point, my cock felt so heavy, hard, and thicker than usual. The head especially. Filled with fluid and ready to erupt, my fat swollen head glistened with precum. I don't produce a lot of pre-cum, but after restraining and prolonging my orgasm, I build up a thick and milky cum shot.

I knew I could cum whenever I wanted to but then the fun was likely over for the night. It was only 7:00 PM and I didn't have any plans for the rest of the night. I would stroke for a bit longer, watching porn and scrolling/chatting on Tinder, before giving myself the great satisfaction of a powerful orgasm.

I had received a response from an old flirt and was catching up, but mostly focused on checking out the profiles of potential hot mature women that were nearby. It had only been a few minutes, but I was not having much luck. I had swiped to the left on a bunch of profiles I wasn't interested in and only right on two profiles. I had an idea or a criteria in mind as I looked through these older women. The honest truth about my fantasies and desires for mature women comes from a time much before meeting Darlene earlier in the night. My sexual interest in mature women comes from years of fantasizing about high school teachers, a close friends mom, and even my own mother. Perverted as it may be, she had many of the physical attributes I loved on a woman, especially a MILF. Pretty, dark haired, large breasts, big butt. So as I swiped my way through Tinder, it was these horny and naughty thoughts that guided me.

Since Tinder provides profiles based on proximity, there was a hope that if Darlene had one, her profile would appear eventually. I suppose my intentions on Tinder had changed slightly. Regardless of the knowledge that Darlene could pop up on my feed, I was shocked when it happened after only about fifteen minutes on the app with my recent age adjustments. The fact that she was on the app was a great sign.

So there she was. My excitement was electrifying. My heart was once again racing at the feeling that my mature neighbor had created within me. My cock quickly grew to full length and a nearly painful stiffness as I studied her profile and slowly stroked myself.

First, I took my time looking at her photos. There were three. The first was her in a white button up blouse. The photo was a portrait shot, from just below her large breasts and up to her face. A slight view of delicious and deep cleavage is available, but this photo truly features a lovely white smile, pretty blue eyes and wavy auburn hair shining in the natural light. An innocent photo but she looked like a total fox. The second photo was an image of her at the gym. Another fairly modest photo, it shows her shoulders glistening with sweat, her pretty face, and her hair straightened and pulled back for her workout. Another basic, yet beautiful picture. Finally, there was a family photo. She had two daughters and a son and three grandchildren. This confirmed not only that she was a sexy mom but she was a grandma! An added bonus was that her daughters were both quite sexy and based on looks, likely just slightly older than me.

Next, I took a moment to read her profile. It stated that she was a divorced mom looking for fun friendships and possible relationships. It also mentioned that she had tried her hand at marriage with a man her age and she was no longer interested in guys her age or older than her so she was more focused on younger men. I excitedly, and with very high hopes, swiped right. It was not an immediate match, but I could hope that it soon would be. In the meantime, I continued stroking my hard cock and searched for another milf porn video to watch.

By this time, the sun had began setting and my room was only lit by the porn video on the television and the light from my phone screen. I had not yet cum, but was extremely comfortable and getting tired. I must've dozed off for a bit. When I woke up, my hand was still on my cock and I felt the vibration of my phone on my chest. I picked it up and saw that I had three notifications from Tinder. I had matched with Darlene and she had sent me two messages.... "Oh hello young man." Followed by "funny seeing you here."

I woke up a little groggy and confused but quickly gained awareness of the situation. I saw that the first message was 15 minutes ago and the most recent one was about 10 minutes after that. It was clear that she wanted to gain my attention and now she had it. I typed a quick and simple response... "It is funny, but I consider myself lucky. And I'm taking your advice - not worrying about those younger girls! What are you up to?"

I waited a few moments for her response. My cock so hard it was twitching. Being extra careful not to cum due to my excitement level, I started slowly pumping my cock. My phone buzzed again... I read her response, "Oh nothing too exciting. I like to get on here during the weekends. It helps spice up my otherwise boring life."

Trying to be friendly while playing it cool, I respond saying that I doubt her life is very boring. I add in that "I love your photos." To my enjoyment and surprise, she responds quickly by saying "thanks for the compliment. I enjoy photography and have plenty of other photos that could be shared." Again, my heart began racing as my balls ached for release. Before I could respond she began typing again and sent a follow up message. "My weeks are boring and busy. I work part time and watch my grandkids the other part. I look for enjoyment on the weekends."

I continued stroking to this increasingly sexual conversation while watching another MILF video. Her comments prompted me to ask "What type of weekend activities do you find enjoyable?"

Once again, she responded quickly as if waiting for my every message. "How about you come over and find out, you sexy young man."

So here I was, horny as hell, still in my baseball clothes, with a chance to have a deeply rooted fantasy of mine come true. Unfortunately, I had not showered and it had been over two hours since I got home. I was about to get up to turn on the shower but decided a quick response would be smart so she would know I was getting ready. "Don't be annoyed... I still haven't changed or showered since baseball. I will clean up now!"

I got up and without turning off my TV or laptop, walked down the hall to start the shower. After starting it I returned to my room to grab a clean towel. That's when I saw a message from Darlene: "Not annoyed at all. In fact, that sounds quite delicious. Perhaps I could come help with the showering process?"

My mind started racing... "What a kinky older woman" I thought to myself. Then I responded and decided to be a bit assertive. I told her "Door is unlocked and I'm sitting on the couch inside. Let yourself in. I'll be waiting." Quickly, I walked to the bathroom and shut the shower off. I sat down on the couch in the dimly lit living room and waited patiently, but not for long.

In less than ten minutes I could hear the screen door open, followed by a gentle knock and then the main door swinging slowly open. "Come in, Darlene" I said as I slowly stood up. We walked toward each other and the butterflies I was experiencing were electric. She looked amazing. She had on a black dress that stopped above her knee. She had dark stockings underneath and a jean jacket on over the dress. Though the dress didn't show cleavage, it was tight enough to accent her curves and show off her tits.

As I approached her I realized that at 6 feet 1 inch tall, I was about nine to ten inches taller than her. We both seemed to enjoy this as she rose to the tips of her toes and I leaned down, embracing each other in a deep and passion filled kiss. We both moaned excitedly as our tongues explored each others mouths. Finally, after what seemed like minutes of passionate kissing, we stopped and she looked up at me and smiled saying "oh man you are sexy. I couldn't be more excited that you are my new neighbor."

I laughed briefly before we embraced again in more passionate kissing. Our hands explored each others bodies. She moaned as I squeezed her ass and firmly gripped her big tits. My hand made its way to her face and neck and she appeared to get even more turned on.

Her hands were exploring my body as well, but now she was using both hands to undo the belt on my baseball pants. Once undone, she unbuttoned and unzipped them, yanking them partly down so that they sat below my ass with my cock and balls bulging out in my compression shorts. A familiar, musky scent returned to the air and my nostrils, and Darlene must have noticed this as well. She stopped kissing me and looked into my eyes with this deeply sexual and deviant look as she said "You smell delicious, John. May I get closer for a better smell?"

I returned the devilish grin and prompted her to get on her knees. I watched as she expertly approached my cock and balls. All of her teasing did nothing but add to the anticipation and make my balls ache more. From above I saw her press her nose against my crotch and breathe in deeply. Letting out a gentle moan at the end before doing it again. Then she used both hands to slowly and carefully grab the waistline. She slowly pulled it away from my body and leaned forward to smell me deeply. Finally, she yanked my compression shorts down and over my cock, causing it to spring to life before her. She bit her lip and moaned as she sized me up. Darlene had experience, and it turned me on. I loved watching this mature woman be such a naughty girl at the sight of a hard, younger cock.

With my pants and undergarments midway down my thighs, my cock was so hard it pointed slightly upward. My big, cum filled balls hung low even though I was close to cumming not long ago. My cock looked quite impressive as it was presented to Darlene. I'm not huge, but approximately 6.5 inches and fairly thick. My pubic hair was dark, but well maintained. In general, I am a hairy guy, especially my lower half. Darlene smiled once again and then leaned forward, with both hands on my hips, and opened her mouth to take my cock inside. I was already hard and at full length and it was apparent that she wanted to taste all of me.

Her mouth felt fantastic. It was warm and wet and clearly quite hungry. She was talented with her lips, tongue, hands and throat. Darlene was able to suck me deep, taking most of my cock, while gently tugging on my balls with one of her hands. She would use the other hand to stroke me as her mouth pumped up and down on my cock. She would alternate her focus between stroking/sucking & taking my cock into her throat. Rarely was her mouth not on my cock but in those moments she looked up at me and asked me dirty questions, such as "Am I getting it wet enough?" and "do younger girls do it better?"

I couldn't help but smile as I looked down and watched this talented, mature woman make love to my cock with her horny mouth. My head was spinning as she worked my cock and talked dirty. I knew if she continued I would explode. So I made the painful decision to tell her to stop. She looked at me with sad eyes so I tried to explain. "If you keep going, I'm going to cum all over and there are still so many things I want to do to you."

She smiled, keeping her hand wrapped around my cock and close to her mouth and then said to me "oh honey, I hope this isn't a one time thing. But if you want, we can switch things up. Tell this sexy older woman what you want to do to her!"

"This is definitely going to be a regular thing.... But for now, how about you stand up and help me get some of your clothes off. I'm going to take my pants all the way off." I replied with a laugh. She stood up and we began kissing again. It was wet and it turned me on tasting her saliva, knowing that my hard, sweaty cock had just been in her throat making her mouth extra wet. I broke the kiss and peeled her jean jacket off. I lifted her dress up and used my hands to direct her to turn around. From this angle, I could see her legs in the dark stockings and her round ass in sexy, dark purple lacy panties. I must've let out an audible moan because she responded by wiggling her ass and asking "Do you like what you see?"

"Oh yes, I love what I see baby!" I nearly yelled as I gave her ass cheek a firm spank. Then I leaned forward and began worshipping her big, round, mature ass. It was thick and naturally big. I was kissing the cheeks and then placed my nose between them and inhaled deeply. I moved my face down an inch or so and inhaled again. Intoxicating scents and I could not choose a favorite.