First of all I want to say that I’m not one of those promiscuous girls who sleeps with every cute guy I meet. It was safe to say when I was younger I was actually very prude. I’ve had several opportunities since then to explore different situations and positions with men. Still I’m not the type of person to give in to every desire or temptation that comes my way. Fortunately I have the luxury of choosing who I want to be with.
For the past couple months I’ve been wrestling with a new curiosity of mine. Since I recently moved to a new place here in California, this new fascination has chiseled away at me. The thoughts and ideas of it have constantly beamed to the forefront of my mind. It wasn’t until recently that a friend pointed out in a conversation that I should explore this fascination and see what could become of it. Reluctantly I agreed with his idea in hopes I could quell the torturous thoughts that I’ve been entertaining. You see, I’ve always wondered what it would be like to sleep with an older man. I’m 28 years old and not exactly young but not even close to being considered old. I feel I’m in my prime right now. I’m in fantastic shape and I feel I’m the sexiest I’ve felt in years. I’m very conscious of my body and I do everything I can to keep my physique in prime shape. I’m not blind to the way it makes men feel and I always enjoy them noticing me. I don’t mind the attention ever. I mean who wouldn’t like to be desired and wanted.
That’s part of the reason for this new wile of mine. What would it be like to be with a man much older than me? I’m not talking about a man in his 40’s or even his 50’s. I’ve experienced that before and I know there isn’t much difference with that age. They are just as lively and strong as a 21 year old. What I’m really curious about is how a man would perform at an age that was far more accelerated. That’s where my neighbor comes in.
Ever since the first day I moved here I’ve noticed him. At first he really creaped me out by the way he stared and followed me around. Every morning when I’d go for my run, he was there in his front window staring at me. If I went to get my mail he would find a way to talk with me. If I were at the pool sun bathing he would always wander over with his dogs and pretend to not stare. It just made me so mad at first because I knew he went out of his way to catch a glimpse of me, which made me feel like such a victim. That was until one day when I started to wonder how he would react if I teased him and gave him a little to see. At first I started stretching in front of his window before my runs. Some days I would lie out by the pool and oil my body just to drive him crazy. If he came outside to walk his dogs in the courtyard, I’d open my front blinds and walk around with just my little shorts on and a sports bra. It was so exciting and so thrilling trying to get his attention. I could tell it just drove him crazy. I kept thinking how he would react if I did something sexual with him or made an advance.
Finally one afternoon I couldn’t take it anymore. A friend and I were talking and he coerced me into exploring the possibilities. He said what could it hurt. He could say no or he could say yes. I wasn’t sure I could make the leap to sleep with him but I wanted to see how far I could get myself. I changed into my cute white cotton skirt. One that was short enough to show off my thighs. I put on a skintight yellow tank top and straightened my hair out. I wore a little bit of lip-gloss just so my lips would glisten and I rubbed some lotion on to make my skin glow. I was a bit nervous but the excitement propelled me to his door. As I knocked on it I quickly came up with a reason to come inside. I had just gone over earlier in the day and asked for some sugar so I knew I couldn’t use that excuse.
When he answered the door I asked if I could use his telephone really quick. I told him I had to return a phone call and it was really important. I would use my phone but for some reason it wasn’t working. Trenton was so sweet and really gullible so it was a breeze getting inside to use his phone. He walked me over to it and told me to call whomever I wanted. I dialed my house phone and pretended to leave a message for a friend. Luckily the walls were thick enough that you couldn’t even hear my phone ring back. My mind raced as I stalled to come up with the courage to make my move. Trenton just stood there, watching me as I played with a pen on the kitchen counter. He kept looking at my legs and staring at them with his mouth open. While I waited for my answering machine, I decided to sit on the stool next to the counter. I pulled the skirt up my legs a little and rubbed my thighs with my hand. I watched as his eyes locked onto the movement of my fingers gliding up and down my legs. Finally I hung up phone up and told him no one answered. We kind of stood there for a moment as things became really awkward. The silence was deafening as Trenton struggled to think of something to say. I knew I had to instigate a conversation or my adventure would be over with quickly. As I stared at him in his little boxer shorts and white t-shirt I could only imagine what his body would look like underneath his clothing. He seemed a little emaciated and thin and I only guessed he would be frail underneath. The thought of sleeping with him grew dimmer and dimmer. I couldn’t imagine doing that with him. The only thing that encouraged the thought was the fact Trenton would be so amused by it. I’m sure the thought of his dick inside such a young woman would be a dream come true. The thought just wasn’t enough to push me though.
“So Trenton, what are you plans for the day?”
“Well not much Leah. I guess I’d watch a program or two.”
Poor guy, I guessed right when I thought he had little to motivate him.
I’m sure seeing me everyday was better entertainment that what was on the television.
“Oh that must be fun.”
Gosh I didn’t know what to say and I was sure I was sounding really dumb at this point. I just stabbed at what ever came to mind in hopes I could spur a conversation.
“I hope so or else my day is shot.”
“Maybe we can have a drink or something Trenton. You know…get to know one another better.”
“That would be great Leah, I would love to talk with you more.”
Trenton and I small talked for a bit. If only he knew what I wanted. What if he knew how I fantasized about him and how I wrote stories about him and I? I’m sure he would just pounce at the opportunity that sat just inches in front of him. Finally after almost a half and hour of talking I mustered the courage to fire in a probing question.
“Hey Trenton would it be okay if I admitted something to you?”
“Sure sweetie I’m here to listen.”
“Well you see, I’ve noticed you watching me since I’ve moved here.”
Trenton suddenly grew bright red. He didn’t know how to react or why I brought the topic up. He shifted nervously in his chair and seemed to avoid making eye contact with me.
“Leah I am terribly sorry. I’d never want to make you uncomfortable.”
“No no Trenton please don’t get me wrong. I was just curious about it.”
“It’s not that I’m nosy or anything sweetheart. It’s just that I noticed you were new here.”
“Is that the only reason?”
“I’m afraid I don’t understand Leah.”
“What I mean is are you only staring because I’m your new neighbor?”
Trenton had a confused look on his face. He really didn’t understand the question. I guess I would have to be more obvious then.
“Do you find me attractive Trenton?”
He sat up quickly as his hands clutched the armrests of his chair. He seemed very flustered and surprised that I would ask such a thing.
“Trenton what I mean is do you like having such an attractive young neighbor like me?”
“Well I think you are a very beautiful woman Leah if that’s what you are asking.”
I giggled as I moved to the seat next to him.
“Do you ever imagine what it would be like to see me naked?”
I was so surprised I would even ask that. His reaction was driving me wild though. I could tell he was caught off guard and unsure of how to react. His meek little seventy-year-old frame was heaving as sweat beads rolled down his forehead. He was too much of a gentleman to answer back so I asked another question.
“Have you ever thought about sleeping with me Trenton?”
Again he just sat there and stared into my eyes trying to see if my questions were sincere. As he sat there motionless, I reached over with my hand and caressed his leg. Instantly I saw his knob twitch in his boxers. Wow I was so surprised that I got such an immediate reaction. As I continued to massage his leg, I could see his member grow and push his boxer shorts up and outward.
“Do you like this? Do you like the feeling of my hand on your leg?”
I realized there was no way he was going to be able to respond. He was in shock and couldn’t grasp the fact that a young woman like myself was coming on to him. Slowly I guided my hand up his leg and over to his crotch. By now his shorts were standing up as the fabric stood out like a tent. I reached into the slit just below his waist and found his dick with my fingers. It was surprisingly firm and decently long. Trenton bellowed out softly as I rubbed his cock with my hand. I could see his heart dance in his chest and the sweat pour from his face. I stroked his dick for several seconds as I watched his hands violently grip the armrests. He was ecstatic; the stimulation he was receiving was immense. As I jerked my hand up and down his cock, I could feel the blood pulsate through his veins, which caused his dick to grow more and more. I stared into his eyes as they almost rolled completely back in pleasure. He kept looking at my hand and looking back at my tits as they bounced lightly from the movement of arm moving back and forth. I fought back the urge to suck his cock, knowing the feeling of my soft hand was definitely sufficient.
As I stroked his cock up and down, Trenton reached over to me and rubbed my thighs. He kept caressing, feeling my calves all the way up to my inner thighs. As I gripped his cock, I felt the head of his penis stretching as it turned a deep blue. When I rubbed it with my fingers, I could see his hips jolt backward due to the heightened sensation. The feeling of my hand on the tip of him was almost unbearable. Finally after minutes of stroking his cock I felt his dick stiffen up so sharply that it seemed to drastically stretch the delicate skin, which enveloped his blood filled shaft. As I pumped his cock several more times, a load of cum suddenly came shooting out of his dick. Trenton screamed out violently as stream after stream of hot ivory cum erupted all over his stomach. His body tensed up as he jolted forward vigorously, almost causing me to lose my grip on his cock. I finally let go of him as I watched his dick slowly soften and shrivel up into his boxers. He was whipped out and completely drained from the whole experience. His satisfaction was only overshadowed by my own. The whole event was so fulfilling. My curiosity had peaked and the outcome was exhilarating. I cleaned my hand off with his t-shirt and leaned over to him as he was still seated back in his chair. As my breasts hovered near his chin, I whispered into his ear,
“I hope you enjoyed that sweetheart. Maybe next time I can taste just how sweet you are?”
I walked over to the front door and looked back to see him smiling with his eyes still shut tightly. His old, meek body shivered from the cold. Although I didn’t get to feel his cock inside me, I knew I could if I wanted to. It was completely up to me.
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