My Neighbor the Dirty Old Man: True Story
by Juliehourglass
If you are under 18... blah blah blah then go do something else. Don't read this or you my might get some perverted ideas.. oh my!
A brief description of my looks : about 5'7", italian slender athletic build, gorgeous legs and ass, adorable pouty lips and cute face. When I would dress up, I prefered wigs and makeup so didn't keep my hair too long but when I did it was shoulder length and curly brown hair.I love to wear pantyhose, heels, skirts, corsets, etc. No need to lecture me on morality. Save it for your church. I'm a well adjusted grown up male who has enjoyed my sensual pleasures in life. My true stories are shared for your enjoyment.
When I was 19 I lived in a small apartment downtown New York. The building was an old run down aparment building on the lower east side with a wide range of tenants. One day when I was coming into the building I ran into an old man struggling with his cane and a bag of groceries. He was a rather large unattractive grumpy old man with smelly breath, a few days beard, and run down ragged clothes. I offered to help him and he accepted. As we made our way slowly up the 3 flights to his third floor walkup he told me a bit about his living situation. He lived alone and rarely had visitors accept from the department of social services to look after his medications and he preferred his hermit like existence to being bothered by many people. In spite of this, he seemed glad to make my aquaintance although very cautiously. After all this was New York. I helped him get into his apartment and put his groceries down for him. His place was an absolute mess and smelled as you might expect a musty old man's apartment to smell. There were clothes strewn about randomly. Old newspapers lay in stacks along the dirty walls. A small television sat on top of a small table in his living room. There was a large green lazy boy chair and a long old brown sofa along one of the walls. For some reason I began to feel a certain twinge between my legs and a very definite kind of arousal began to take place as I was about to leave. Even though he was a cranky old guy, I could see him checking me out in a somewhat unappropriate way through his thick large glasses.
One of my many perverse enjoyments is to be fondled and ogled by a dirty old man... and this was certainly a dirty old man, but I was not so sure he was dirty in the right way. This thought occured to me as I was about to leave him. I didn't want to push anything with him since he did live in the same building as me and I didn't want to create any problems for myself with any neighbors. I thought it best to continue with him at a different time and said good-day.
A week had passed and I hadn't seen him at all. I wondered how I could find a reason to knock on his door and see if he had any interest beyond what I had seen so far. I thought of an innocent enough reason to knock on his door. I would stop by and tell him I was heading to the local market and could pick him up something if he needed it. This would make it possible for me to know if he'd talk to me again, and also to tell him when I could come back - which would be much later in the evening - under the pretense that I would be out for a couple hours. I knocked on his door and he shouted loudly "GO AWAY!". I think he must have thought it was someone intending to harass him. I said, its me J, your friend from upstairs Mr. Olmert. I came to see if you needed me to pick up anything from the store for you. Then there was silence. Suddenly I heard the door chains being removed and the door unlocked and opened.
There he stood looking even more unruffled and disoriented than last time, however he said "oh its you..." he studied my face through squinty eyes. "I could use some milk ..? I said no problem and would it be ok if I came by around 10pm to drop it off since i'd be out for a couple hours?"..... since my plan was to make my femme self available for him later, if he should want to partake.... He said that would be ok but he usually wasn't usually up that late. I still couldn't tell if he was interested or not... so I'd have to be extra careful how I handled myself later. So off I went with only one thing in mind. I picked up the milk and returned to my apartment to pick out just the right outfit to wear!
Since I'd have to appear to be dressed like a boy but also leave the option open for more, if it came to that... I'd have to look like I was just hanging out dressed in my calculated outfit...It was easy to keep my legs and clitty smooth and hairless. The rest of my body had only minor hair which was not noticable. I mostly wore khaki pants in summer no one noticed the exceptional smoothness of my legs. Also my hair was somewhat long and curly at the time and so this lent itself to looking very femme when i put on some light lipstick and mascara if I wasn't going to wear a wig....which i wouldn't wear this evening. I applied enough to look like I wasn't wearing makeup, but give my face a decidedly femme and smooth look. For an outfit I chose to be simple and somewhat femme. I had a pair of very tight and short denim cut-offs that just covered my perky ass cheeks and hugged my slender hips. My smooth legs looked absolutely stunning in them, although I wouldn't dare just walking out in public dressed in them. However tonite I was intending to look as if this was how I dressed around the house without appearing to have put any effort into it. My bare feet are smallish and pretty and also tan so it was natural that I might also be barefoot. For this adventure, I would use some pale pink nail polish on them. Underneath my cut-offs I wore a pair of tiny black satin panties which hugged my boy clitty like a snug glove. I wore a button down tapered blue pin stripe shirt which hung just to just above my ass cheeks, leaving the back of my creamy thighs totally bare. This allowed me to conceal the guazy black bra I wore underneath when I walked down the two flights of stairs to get to his apartment. I looked in the mirror and saw that I had succeeded in creating the illusion of a very femme looking boy with very girlish features, but not dressed as a girl. Now the next part which had me really nervous... how to walk down the two flights of stairs to his aparment.. I'm sorry if this story is too long but each part of this erotic adventure is needed to setup the frame in which it took place. I was scared to death that I might be discovered accidentally by a neighbor if I walked out in such a femme and revealing outfit.. especially barefoot and with pinkish toe nail polish highlighting my delicate tan feet. So I waited another few minutes and I grabbed the quart of milk and slowly opened the door, listening for any noises in the tiled hallway and stairs... it was silent!
I was so turned on at the thought of what might happen I almost had an orgasm right in my panties. I stepped out onto the cold tiles of the hallway and began moving toward the stairs. Quickly I made my way down the two flights, and delicately made my way down the darkened hallway that led to Mr. Olmert's apartment. I could feel the snuggess of my panties and the femme feeling of my bra rubbing against my nipples and the shirt. I was so turned on as I got to his doorway, I almost had an orgasm there too! I breathed in and tried to relax my quickly beating heart, then I knocked lightly on the door. Again he yelled "GO AWAY" to which I responded quietly, "Its J and I brought your milk." Again, silence then the familiar chains being unlatched and the door opened. He looked as if he had just awakened. He was wearing a long robe and some pajama bottoms and slippers. His apartment was dark except for the television in the background. He looked at me not saying a word. Then he said, "thanks... how much was it?" I said it was only a dollar. He reached into his robe pocket and asked if I could wait a minute while he got money and opened the door to let me stand in the doorway. As he ambled over to the table he told me he was dozing in his chair when I knocked and apologized for yelling at me.. then he said in a raspy cranky voice, "you've got really nice legs, did you know that? They look like a girls legs." Then he started looking more closely at me, squinting and his eyebrows appeared to cross and he started to look like he was getting mad... but he was struggling to understand my appearance. His mouth started to open a bit, then he became more awake with a slight smile.
I was a bit embarrassed by his comments since the door to the hallway was open as he spoke although not that loudly, but I was afraid someone might hear it and detect what I was up to. I started to feel like I wasn't getting the response I wanted and thought I should just get going and play out the rest of my sordid fantasy in the privacy of my apartment. I guess he may have been a bit drunk or simply loopy from being asleep, but then he said I should step in and close the door while he got my money. Then I knew he was interested.
I closed the door behind me shutting out the dim light of the hallway, and removing the risk of the neighbors possibly hearing our conversation. With my bare feet I could feel the dirt on the floor as I moved deeper into his apartment. I felt even more femme as slowly made my way into his dark apartment, not knowing where he'd gone to get my dollar. I don't know why, but I was so turned on at that point, all I wanted was for him to yank down my cuttoffs and suck and fuck me..
Soon he came back from his dark bedroom and handed me a dollar. He thanked my for doing him the favor. Then I was shocked by what he did next. He put his hand into his pajama bottoms and appeared to be rubbing his cock while looking at me. He moved toward his chair while rubbing his cock and sat down. His robe was open and I could clearly see that his pajama bottoms were quite worn and rested loosely over his hand as he did this. He said, "you look different than you did earlier. You look alot like a girl. Come closer so I can get a look at you... " And with that I slowly made my way toward him giving up any pretense of a neighborly favor. I could only hope that he would not reveal this to any of the neighbors.. at least for my safety, but it was way too late for that kind of thinking now... my fantasy was coming true. This was so delicious.
There were no commands or forceful actions he just started to run his free hand up and down my legs as I stood to the side of his chair. He pulled me toward him forcefully and began to press his fingers up under the bottoms of my cuttoffs all the while he was breathing with his smelly breath right up to my ass. My boy clitty was getting very hard and I felt as if I might cum right there from his forceful caresses. He moved his hand up under my shirt and began to feel of my chest and bra which was not filled. Then his hands proceeded down to the front of my cuttoffs. All of his sounds were very disgusting and pleasurable at the same time. His fingers were kind of fat and hard and dry.
He told me to move to the front of his chair and stand between his legs and to unbutton my shorts, so I did and let them fall to my feet and he let out a sigh of pleasure as they fell. All the while I was standing with my eyes closed enjoying his fondling, He was stroking his long hard cock slowly and pushing down his pajama bottoms. When my perfect ass was in front of his face he pushed his mouth up against it and pulled my panties down below my buttocks. He was licking my crack and biting my ass and rubbing his hard whiskers into my ass cheeks. It felt unbelievable. I began to cum in my little panties which still covered my clitty in the front. Then he put his hands on my hips and started to push me down onto his hard cock. It really looked rather long and thin. I asked if he had any lotion we might apply for a lubricant and he said " awe shit, c'mon I wanna fuck ya"..
He said if wanted to have his cock wet then I'd have to suck it first... and so that is what I had to do. In spite of the fact that he was a disgusting smelling old man, I got down on my sexy smooth little knees with my panties still around my thighs and began sucking on his smelly cock. Soon he was very hard, slippery and wet from my skillful oral service and he started to pull my hair. He pushed his cock into my mouth and the back of my throat. I almost started to gag, but also I could feel a twinge between my legs at the same time as I detected his orgasm approaching. He said he had no idea what hot bitch slut I was when he saw me the first time, but he said I turned him on when I came over tonite dressed like such a little slut... and all of this coming out of the mouth of my neighbor!
Then he told me to stand up and turn around, that he wanted me to sit down in his lap so he could push his hard cock into my hot pussy. I pulled off my panties off so now I was wearing only my shirt and bra underneath. I sat down slowly into his lap until I could feel the head of his wet nasty cockhead at the entrance to my eager pussy hole. It took a few tries but he pushed into my boy pussy with only a slight amount of pain. It was a sharp pain when it entered and I swear I saw stars briefly but it was soon followed by waves of pleasure which quickly took over my body. His body felt like a large pillow with pointer going right up into me. He was holding my hips and saying what a naughty girl I was and I was such a slut to show up at his doorway tonite... and he said my pussy felt so good. I could feel his cock inside of me as he pushed it up into me as far as I could take it. Thankfully it wasn't too big for me.. Soon we were rocking in rhythm and he was rubbing my g-spot and my own orgasm was becoming so strong I was almost falling off the chair. He reached around to fondle my boy clitty and my gently caress my shaved ball sack. I started to feel the spurts of his warm old man come shooting into my ass and my boy clitty began to spasm and shoot my juices all over my spread thighs and his robe and chair. It was absolutely mind blowing... We were both completely exhausted and I slumped back into his arms with him still inside me afterward... soon he withdrew his cock and I got off his lap. I put my shorts back on and left my panties for him.. gave him a quick peck on the cheek goodnight.. and said this is our little secret right? He smiled tired, and nodded yes..
This was much more than I had expected, but it was a most satisfying fantasy that came to life. We only met up a few more times and then he moved to an old folks place outside the city. We didn't stay in touch.. but I'll try to write about one of the other times we had a chance to play.
I hope you enjoyed my story it is completely true. If you'd like to write me, feel free. I'm sorry about my old email address.. something went wrong with it.
Juliehourglass
tgpantyhose@gmail.com