I have always been intrigued by anything to do with sex. When I was 5 or 6 years of age I would find myself looking in the Sears catalog at the women’s bras and panties section. I don’t know why but it was just so interesting to me. Then, when I was 8 I hit the mother load. My parents had a collection of adult cartoons as well as playboys and other type nudie magazines.
I remember reading them and staring at all the pictures of both women & men. Some of the cartoons had pictures of humans with a****ls. That too was very exciting to me. I never really had an orgasm when I would look at these magazines, but I would get a hardon.
As I got braver, I found myself looking up my aunt’s skirts and even at my mother when she would get out of the bathroom in only a towel. I would sneak peeks at here ass when she wasn’t looking.
This kept on for several years. Till one day, I was helping her get our laundry together and I noticed a pair of her panties, which had a smeared stain in the crotch. It wasn’t a stain like the usual sk** marks most k**s have. It looked like she had wiped something off on them. I don’t know what possessed me to do it but I took the panties from the laundry basket and held them up to my nose and sniffed. It smelled sweet yet tangy. Then what I did next amazed myself and I was careful not to get caught. I stuck the tip of my tongue out and tasted my own mother’s soiled panties. I could feel the bl**d rushing through my head as I began to get a hardon. Yet, I still had to learn how to masturbate.
For the next several months I found myself helping mom with the laundry every weekend. She was the only female in the house, so I had never smelled any other woman’s panties. Although, every time I would go visit my cousin’s who were girls I would go to the bathroom and look for theirs or their mom’s, (my aunt’s) panties to sniff. But there was always the fear of getting caught that kept me from doing anything other than sniffing.
Until, the summer came around and I had the good fortune of being asked to watch after our neighbor’s dog. The fortunate thing about that was that it was only for the weekend and my neighbor had 3 daughters. My neighbor herself was an incredible looking woman with blonde hair, a nice butt and huge breasts.
Fortunately for me, since they were only going to be gone for the weekend, they had apparently left in a hurry. And because of the rush to pack and leave they hadn’t done any of their laundry. I recall going over several times throughout the day to check on their dog. Each time I would rummage through their laundry sniffing all the crotches and even sucking on them. It was incredible.
That is when I got the idea, I remembered the times that I had peeked in their window late at night during the summer and seeing my neighbor stark naked, and how beautiful her body had looked. I wanted to know what it would feel like to be her. So, I began to undress, since there was no one around to worry about. I stood in front of her full length mirror and looked at myself. I was 5′ 4", maybe 110 lbs., flat stomach, nice legs and butt, and a hardon. Being that I was only 13 I still had very little pubic hair. So, there I was, butt naked in my neighbor’s house. I was loving every minute. Something inside me told me to try pushing my cock back between my legs. So, I slowly tucked my cock back till it as well as my testicles were out of view if you were to look at me directly from in front. I turned to see what it looked like from behind. And giggled at the site of my hard cock, pointing up, yet upside down, between my butt cheeks. I turned back around and faced the mirror. If I hadn’t have known I would have thought I was a naked little girl with a small chest. Because of the way my cock was tucked, the few pubic hairs were shaped just as a woman’s pussy looks. It was such a turn on. I squeezed my thighs together and pushed my ass back to make it look even more feminine.
That’s when my imagination took over. Suddenly, I found myself in front of the mirror thrusting my ass back and then thrusting my pelvis forward. I began to grow weak in the knees, and slowly laid myself down in front of the mirror looking at myself, with my feet spread far apart but my thighs still clenching my cock. I looked at the mirror and watched as I thrust my pelvis up and down in the air. Because of the view I had I was able to see my cock wedged between my butt cheeks, it was incredible. If I looked straight across my stomach. I felt like I was looking at my very own little pussy. I kept thrusting and thrusting feeling my pleasure grow. Then, without warning, I felt my body begin to convulse, which scared me. I thought I was going to pass out. I started to panic and that’s when I felt the fluid squirt from my cock onto the back of my thighs. I had cum for the first time in my neighbor’s bedroom all over the floor. I continued to do this as soon as my cock was able. I must have cum at least 3 times before heading back to my house. This was just the beginning of how I became addicted to sex.
After my first day of learning how to masturbate by placing my cock between my thighs and rubbing them together. I was addicted. I would find myself going to the bathroom for long periods of time and actually, lying on the floor with my legs squeezed around my cock. It was such a great feeling. I assumed that this must be what women feel, when they orgasm. Because of the feminine way I looked, with just my pubes showing while my cock was back between my legs.
It was because of this assumption that I began finding myself more & more intrigued with everything that had to do with femininity. I would often steal a pair of either my cousins or my mother’s panties and wear them while having my cock tucked. It was such a nice feeling walking around and feeling my thighs rub against my cock.
I was a very thin yet attractive young man at the age of 13, and was into running. I was about 5’4", 110 pounds, with very strong muscular legs, with thick thighs, round hips and a plump but toned butt. I would jog around the neighborhood, in really short shorts and tank tops or no shirt at all. I would notice the second glances I would get as I jogged from the neighbors. Most of them just kinda would smile & I’d smile back. I have really great dimples and was not shy about showing them off. There were a few neighbors mostly men who would jog with me. We didn’t talk about much. But I could feel them checking me out. It was such a turn-on when I jogged because I usually had some skimpy french-cut panties, or a jock. I knew that the area where my legs met my butt was exposed to those who would watch me run by. Usually I ended up with my shorts wedged up between my butt cheeks as I jogged. I never would tuck my cock when I went jogging. It wasn’t as pleasurable then. However, the shorter the shorts the better. I could feel the air against the exposed part of my butt and it was nice.
I started to notice that there was this one gentleman that would make it a point to be outside no matter what time of day I would jog. I knew he had to have been watching for me, because several times he would hurry out to the edge of his lawn near the street just as I approached his yard. He must have noticed me as I would come over the hill and down into a gully right in front of his house. He’d find some reason to be near the street and would wave to me as I passed by and smile. Most of the time I would wave back and continue on by, but sometimes, I’d start to walk just as I was coming up to him and take a little extra time as I would head up yet another hill on the other end of his yard. He got a really great view of the little bit of my butt cheeks that were peeking out from my shorts. On the days that I had stopped to walk by. I would get home and walk into the bathroom and turn my back to the mirror and then look back over my shoulder to see what kind of view he had. There were a few times that you could see the shinny silk from the red or pink panties I was wearing. I would also bend over and look back between my legs to see what kind of a view he had on the days that he was near the street on his knees working on the yard. This was such a turn on, that I would drop to the floor and tuck my cock back between my sweaty thighs and work myself into a delicious orgasm. I thought to myself this is the power that women have. No wonder they have so much fun teasing me & other guys.
But I wanted to learn more about the pleasures that women felt and started to experiment with the idea of having someone enter my ass, just as they would a woman’s pussy. When I would shower, I would start by lubing up a finger with lots of soap. Then I would slowly work it in my virgin asshole. It felt nice.
I soon learned to combine tucking my cock back while fingering my asshole and increasing the intensity of my orgasm. Once that started, I had to do all that I could to increase the pleasure. I started to use more than one finger and moved onto experimenting with vegetables and fruits.
I would get home and grab a carrot out of the refrigerator and run to the bathroom before anyone got home. I’d take out the vaseline and lube up the carrot and would slowly start to fuck myself in the ass. Sometimes I’d wear panties and fantasize that I was a woman being deflowered. I’d simply pull the panties to the side, while tucking myself back and then slide the carrot right up there. However, I still felt that I could handle something larger than a carrot and in fact felt I needed something larger.
I had noticed in some adult magazines that my parents had that were there were women who had photos of themselves with carrots, bananas, & cucumbers. Having already tasted the pleasure of the carrot, I decided it was time to move on to bananas…it was a painfully sweet experience. Especially afterwards when I would peel back the skin and eat the banana.
The real challenge came when I tried a cucumber for the first time. I thought I’d killed myself. I had lubed the cucumber as much as possible and began trying to squat on it. When my sphincter gave way and allowed that huge cucumber into my ass, I felt what women must feel when they lose their cherry. I had to have hopped from that thing like someone had just put a flame against my butt. I had, in fact broken my own cherry asshole because afterward I noticed that there were traces of bl**d blended together with the vaseline on the cucumber. I was frightened that I would be in need of medical attention, but fortunately it didn’t bleed for long. The next day I could hardly sit up straight. I was so sore. Yet the soreness was a reminder of how much fun I had the previous day.
Having learned how much fun this was combined with my constant teasing of my neighbors. I decided to step up my fun as the summer started to come to an end. I took a couple of pair of old pants that I had and asked my mom if I could make them into shorts since we were probably going to buy new clothes when school started. She agreed since they were already too short in length for me. The previous year I had only been 4’9" and had grown during the school year and during the majority of the summer. She asked me if I wanted her to cut them and hem them so that they wouldn’t fray. But I told her I’d go ahead and do them myself, since I was growing up and had to start learning to do things on my own. Needless to say, I cut them very high on the backside and didn’t bother to sew a nice hem, the frayed look was what I was wanting. I washed and dried them several times, to get just the right type frayed look. When they were just right I put them on and looked at my butt in the mirror.
They were perfect! You could easily see the white untanned roundness of my asscheeks as they met the tanned firmness of my muscular thighs. I then tried them on with my jockstrap so that my cock wouldn’t fall out of the front. I had to do something about the bands that wrapped around my thighs though. It was obvious that I was wearing a jock. I solved this problem by sliding the bands up my buttcheeks and notice that they actually helped to pull my cheeks apart ever so slightly and I could actually feel some cool air blow up the shorts and across my puckered asshole. As I looked back again, I had to grin at myself in the mirror. It was just too nice. The white frayed threads of the faded blue jean shorts, against the background of my well-tanned thighs and the virginal whiteness of my butt.
By this time, I had gotten into a routine of going jogging after my parents left from the house, both in the morning, and after they had come home to eat lunch. This allowed me to take my time and there wasn’t as much traffic. My friendly neighbor must have figured my schedule out as well. Because, he had become quite the lawn man at both those times of the day. Apparently his wife left the house around the same time that my parents were gone. Both he and his wife were in great shape. I didn’t realize that he was married till the middle of summer when he and his wife both started working on the yard. After that I’d see them on my weekend jogs and they’d both check me out and they even jogged with me a few times, not really saying much. Sometimes, he would jog, sometimes it was here and there were only a few times when they both jogged along. I felt that they were sizing me up.
Well, having made my new cut-off shorts, I did to see their reactions. So, I wrapped a bandana around my forehead and put on my socks & jogging shoes. I didn’t bother with a shirt. Then I headed out the door. I had to see his reaction first so, I did this during the middle of the week. I was coming to the top of the hill in front of their house when I felt the twitch in my puckered asshole and the butterflies in my stomach. I started to wonder if I’d have the guts to jog past him in these most revealing pair of shorts. I decided that I had come to far to turn back. I came over the hill and sure enough there he was sitting in the lawn watering his flowerbed near the front of the yard.
As I approached his yard, he started to stare. I know he must have been intrigued by the cuteness of the frayed cut-offs. He waved and I was waved back. I continued forward, with my head starting to spin and the butterflies churning in my stomach. I could feel my asshole began to pucker even more. Just as I was within a few feet he greeted me with a friendly hello. I responded by saying hello as well and I stopped jogging and began to walk.
As I neared him, he said, "You look a little winded today."
I thought to myself, "No, not winded, just really nervous". I smiled and said, "I guess it is the heat."
He looked up to the sky and there wasn’t a cloud in sight. He said, "Yep, no clouds to give you a break from the heat today." Then he added, "But it’s helping your tan, that’s for sure."
I said, "Thanks, I was hoping to go back to school looking like a lifeguard."
To which he responded "Well, you definitely got the swimmer’s build and tan. Plus, your legs look really nice and powerful."
It was then that I realized a rather unique way to give him a better view of my backside, while at the same time giving myself a chance to see his reaction to the back view of both my new shorts. I noticed that although he had stood up, he still had part of the water hose in his hand. The nozzle was resting on a couple of rocks and trickling its cool stream of water into the flowerbed so as not to damage the stems of the flowers. I brought myself to a full stop and asked him if I could have a quick drink of water, the heat was really getting to me. He readily said for me to go ahead.
So, with a little bit of hesitation, as I thought to myself, I might not get this chance again with the summer quickly coming to an end, I turned my back towards him and bent over at the waist as I reached for the nozzle of the water hose. Since I knew where the hose was I looked back around my thigh to see if he would also seize the opportunity to catch a glimpse of my butt. Neither of us was disappointed.
His eyes, started at my waist and went down across the faded cut-offs, over the frayed threads, and directly at my buttcheeks. Having been jogging the cut-offs were farther up my crack than they had been when I had inspected myself before leaving. In fact, they were almost entirely up my crack. As I began to drink from the end of the water hose, I continued to glance back through my peripheral vision at him. I may have just as well been wearing a thong, so much of my ass was showing. His eyes didn’t leave my ass. His mouth opened as he smiled and licked his lips. I finished my drink and turned to face him.
Smiling at him, I took the hose and held it over my head and let the water trickle down my body, rinsing the sweat from my chest and back. I completely soaked my body and the shorts, then I turned away from him again and slowly bent at the waist to replace the nozzle back to where I had picked it up. Giving us both one more eyeful. I took a glance at his shorts and smiled to myself as I noticed his bulge. I thanked him for the water and walked away and began jogging again.
The thrill of that moment was so intense, that I went home and quickly stripped as I walked in the house. I went straight to the refrigerator and grabbed the longest thickness cucumber I could find. I fucked myself into ecstasy, as I gave myself one hell of an orgasm. I woke up the next day and was still thinking about that moment I couldn’t wait to go jogging.
As soon as my parents left the house, I got into my jogging gear, my cut-offs and bandana and headed out the door. I made it to his house earlier than usual because I had rushed myself out the door. He had just stepped outside as I came over the hill. He looked surprised that I was already coming toward their house. And then, made his was to the water faucet and noticed that he had rolled the hose up and that he would have to unroll it in a hurry in order to make it to the street as I passed their yard. I didn’t want to miss another opportunity at getting a drink and putting on a show, but something told me that I shouldn’t slow my pace either, or else the game would be over. I continued at my pace as he hurried to get the hose unrolled. I smiled as I noticed that in his hurry he was actually taking longer by tangling the hose.
I stopped jogging at the bottom of the hill, just as I neared the edge of one side of his lawn. Looking over at him. He gave me a look as if to say, he was sorry that he wasn’t ready. He waved, smiled and said hello but he looked like he had just lost a race. I felt flattered, but at the same time, I was a little disappointed because I knew that I was not going to be able to put on a show. He must have noticed this, as he dropped the hose. Then he gave me a very uneasy smile. I could tell he was a little uncomfortable as he spoke to me.
He said, "Sorry, I didn’t have the hose out in time".
I replied, "That’s okay," and then with a bit of a tease I added, "I guess, I’ll just have to do without a drink today, thanks anyway."
"Well, if you want you can come inside and I can get you something to drink," he replied.
I hadn’t expected this. Now I was put on the spot. I decided, it would be nice to see the inside of his house, and said, "That will be fine, if it’s not too much trouble?"
"No trouble at all" he offered. So, I made my way up his sidewalk to the front porch. He met me at the front door and led me in. As I walked in front of him into the house, he placed his hand on my shoulder blade and let it slide down to my waist.
This touch sent chills through my body. I turned to him as he followed me in. I said, "You probably got sweat all over your hands."
He smiled and laughed. Then said for me to relax as he went to get me a glass of water.
I tried to relax as I looked around his living room area, but couldn’t shake the nervous feeling I had. When he returned he had poured me a drink into a big plastic cup like the kind you get with fountain drinks at fast food places and gas stations. I smiled and said thanks. I decided I’d give him a little bit of a show as I turned to walk back to the door. I took a few big gulps as I walked away from him and finished almost all of the water. Then as I squeezed the plastic cup with my hands, which were wet from wiping the sweat from my forehead, I accidentally squeezed the cup right out of my hands and onto the floor. Fortunately for me, I had finished almost all but a few drops. I looked back and apologized as I reached down to pickup the cup. Although he had made a quick survey to see how much water was spilled. His eyes quickly set upon my buttcheeks as he told me not to worry, that I hadn’t really spilt much and that it was only water and wouldn’t leave a stain. I apologized again as I continued bending over testing the spill area to assure myself that I really hadn’t caused any harm.
That’s when I felt him step close to me and then he cupped his hands upon my asscheeks. I pulled forward, in disbelief. I had thought about such a moment, but was startled by the realization of what he had done. I looked back at him. He gave me an uneasy smile and said "I’m sorry, but you have such a wonderful ass, I just had to squeeze it." I smiled nervously and replied "that’s okay, do you really think I have a wonderful ass?" as I turned to give him another look. I looked back over my shoulder as he examined me fully, now that he had my permission to look me over. I arched my back and pushed my butt up and back towards him as I placed my hands on my waist. He kneeled down and was directly behind my ass. I looked down at him as he responded "Yep, that is a great ass, you aren’t wearing any underwear are you?"
"Well I am wearing a jock, does that count?" I said.
"No way, you are wearing a jock, where are the leg bands that usually wrap around the thighs?" he questioned.
"Um, well, I kinda pull them up like a thong, I have to wear something or else my penis will fall out the front of these shorts" I explained, being careful to use the word penis as to give the impression of being innocent.
"I really didn’t know what I was doing when I cut the pants into shorts, and had cut them shorter than I had planned." I explained, although I knew that was a lie.
He laughed and with a smile said "Well, they are short but you’ll get no complaints from me or my wife, we’ve both thought you have a great body, especially your legs."
"Really?" I asked with surprise in my voice as I turned to face him.
He went on to explain that they had enjoyed watching me walk by and really appreciated the beauty of my young body. I was surprised that to hear him offer that his wife had showed an interest in me, as well. I felt that I should return the compliment and informed him that I had thought that they both had hard bodies, and that I hadn’t failed to notice that. I then asked how old they were, he was 38 and she was 34. He asked my age and I said 13 with some hesitation. He laughed and said he wished he was younger. I had to take the chance and ask why he would say that. He said with a smile as he laid his hands on my shoulders and turned me around and guided me to the table near the front door. As my waist pressed against the table he continued to press against the back of my shoulders forcing me to lean over the table and once again giving him a great view of my ass. He then said, "Oh yes, I wish I was younger, you’ve got a great ass."
Directly above the table in front of me, was a picture frame wall mirror. I looked into it and could see him eyeing my ass. I could feel the coolness caused by the air conditioner cooling the sweat on my buttcheeks, and realized that as before due to the jog, I had worked them up so far that I had turned my cut-offs into a thong.
I watched in the mirror as if I was watching someone else, he slowly slid his hands down my bare sweaty back and onto my waist. From there he slid them along my waist and across the roundness of my hips and down the sides of my thighs. Then he circled his hands up the back of my thighs and cupped my asscheeks. I continued to lean forward as I looked in the mirror as he watched his hands trace my body. He squeezed my asscheeks hard, and I let a gasp escape my lips. He glanced up at the mirror and looked directly at me as if to say, "Yes, I know you like this!" I couldn’t hide it, I was enjoying every bit. He must have been at least 6’2" and towered over me. He had to squat ever so slightly to be able to reach my ass with his hands. He took a good handful of my asscheeks and spread them apart in the process he lifted me up onto my tiptoes as I struggled to keep my feet on the ground. I braced myself against the table as I felt him change the position of his hands as he slowly released my cheeks. He squatted down behind me and with his thumbs on the inside of my asscheeks, slowly spread my cheeks far apart. That’s when he said, "You have a cute puckered asshole too" I could feel the warmness of his breath blow against it. Then I felt it. He stuck his tongue up to my asshole and I thought I was going to come right there, I gasped out loud. He had worked his tongue around the small piece of jeans that remained in the crotch of the pants. Before I knew what was happening he had reached in front and unzipped my cut-offs and was pulling them along with my jock down my thighs and then I surprised myself by helping him as I stepped out of them completely. Wearing only my bandana, and my socks and shoes, I leaned forward against the table. Granting him full access to my puckered asshole that was literally sucking his tongue inside. I had never thought of this. He continued to fuck my asshole with my tongue while reaching right up between my thighs and grabbing my hard cock. He started stroking it. It was incredible. Before I knew what was happening. I had shot my load into the palm of his hand. He stopped tongue fucking me and then took his cum soaked hand and slid it up my asscrack. Smearing my own cum over my asshole. It was nasty but it turned me on. He said to me "You’ll have to work on that, you don’t wanna cum to soon, it can ruin the fun. But, now it’s my turn." I thought for a moment that I was going to have tongue fuck him and I wasn’t prepared for that. As he rose from behind me, I started to turn to face him, extremely nervous. But he caught my shoulder and returned me to my position. I looked at him in the mirror as he quickly stripped. I stood there in shock as his hardon appeared in the reflection in the mirror. He was bigger than me and thicker than me also. My asshole puckered as I compared it to the cucumbers I had used on myself. As it puckered I felt my thick gooey cum that still coated my asshole. He looked at me in the mirror and said, "I thought of fucking my ass all night long, ever since the day before when I had stopped to get a drink." With that I saw him take his cock in his hand and then as it disappeared my reflection, I felt his free hand pushup and out on my asscheeks. I felt him place his cockhead against my asshole and then I felt the pressure as he began to shove it in.
Things were going farther than I had planned. Even if I may have fantasized about this, I never expected it to happen. I couldn’t believe it. I could feel his cock as it pressed deeper and deeper into my ass. My own cum was lubricating his cock. I relaxed my ass muscles as I realized that I should enjoy it and not try to fight it and risk, hurting myself. After the first couple of slow strokes. He began to develop a rhythm. I was literally holding myself up as my feet left the ground. He had grabbed my waist and was fucking me as my body hung suspended from the floor by his cock, his hands on my waist and my bracing myself against the table. He mentioned that I must have been fucked before since I was taking him without complaining of pain. I told him that although it was painful, it felt great. I had never been fucked but that I had used vegetables to fuck myself. He laughed and asked if I had ever used a cucumber? I giggled and said "yes", and then I gasped, as he thrust very hard inside of me with encouragement of my response. He pounded in and out of my asshole, as I looked in the mirror, I saw the sweat on his forehead. He said, that he new I had to have had some experience, and asked, if I liked this. I had to say yes. He said he was getting ready to cum, and pulled me back away from the table holding me impaled on his cock as he shot his load up into my ass. Because our bodies were joined at my cock filled asshole, I could feel everything his cock was doing, the spasms, and the jerking and the fluids coming up the shaft and emptying it to my asshole. He held me for a little while then lowered me to the floor. Allowing me to drop to the floor with my asshole up in the air, as his cock slid out. I laid there, in disbelief. I started to get up and that’s when I felt the cum squeezing out of my asshole. I reached back to catch it so I wouldn’t stain the carpet. He looked down and said, for me to taste it. I looked at him as I licked the cum from my palms. It tasted salty yet… bland. He then grabbed me by my face cheeks and placed his cock to my mouth. I took it in my mouth as he told me to suck it dry. I did as I was told, then I got my cut-offs and lead me to the door. After putting them on. He gave me a wink and opened the door. He thanked me and said, we’d have to do that again. I agreed and made my way back to the street and hurried home. When I got home. I still had some cum leaking out of my asshole, and sucked the crotch of my cut-offs clean. I masturbated, as usual with my cock tucked back between my legs, and relived that moment. It was incredible… and I was grateful that the summer wasn’t quite over yet. This really happened and I had more encounters like this… but more importantly I continued to experiment with all types of sexual activities… I was addicted…