When I was a younger man I lived in a wooded area out side the city of Vancouver Washington. I used to love going out into this tree farm and masturbate. I would wait until it was dark in the summer time and put on a pair of shorts with no underwear on and go out amongst the tree's and take them off and walk around nude from the waist down. I so enjoyed the feeling of being free like that, I would eventually get hard from that feeling and jack off. My masturbation evolved as time passed by, I started wearing a cockring that I made out of a couple of brass rings, one smaller than the other and connected together. The larger one would go all the way around my cock and balls. The other smaller one went around the base of my shaft. I loved the feeling walking around nude with my ring on. Usually by the time that I got to this tree farm, I would already have a hard as rock cock. Once I was like that it would be impossible to remove that ring. I could only get it off after I ejaculated, so I usually would cum before I put my shorts back on. I didn't want anyone to see me walking down the road away from the tree farm with a big lump in my shorts.
On one of my outings I found this old stump that was in a small clearing. I had started carrying a small tube of Vaseline with me when I went out. Once I got to the tree farm I would walk in as far as needed, not to be seen from the road, pull off my shorts and head toward the stump annointing my member as I went with the Vaseline. Once I got to the stump I would get on top of it a squat down with my legs spread and work myself over, sliding my hand up and down my slicked up pole. When I was about to cum I would stand bolt upright with greased pole in hand, ring tight around my cock and balls, and see how far I could squirt my load. This was my favorite thing to do in life. There was know one around and I just loved cumming out there, the release was fantastic.
I had probably gone out to the stump at least 50 times over the course of a couple of months, rain or shine I would do my little routine with my homemade cock ring. One night or should I say, late eve, I had made my way back. to my favorite spot, was doing my standard squat and thrust routine with my solid brass rings on. All of a sudden I felt a hard pinch behind my balls and a severe tug on my cock pulling me to my knees and hands. I resounded with a yell and my heart jumped! I was startled beyond anything that I have ever experienced, I was scared to be honest about it. With my ass up in the air, on my hands and knees I heard a womans voice say, "Put your hands behind your head". Thinking it was the police for some reason, I did what I was told, besides, whoever it was had me by the proverbial cock and balls. When I put my hands up, I felt something go around my left wrist, a tug on my right hand by my assailant pulled my two wrists together and a strap of leather synched my two arms together tying my hands high above my back. Next I felt a strap of leather pull up inside my ass cheeks and more pressure put on my cock, which was bigger than I think I ever felt before, locking the ring on me harder than ever. With my hands tied up and the strap connected to my cockring, some sort of clip and a strap that went up in between my ass and connected to my hands so if I tried to move my arm over my head it pulled harder on my member. " STAND UP!" She shouted at me, and I struggled to my feet and she pulled me from the stump and pointed me towards a dense section of forest where a foot trail made itself evident the closer we got to it. She must have had the strap doubled up in her hand, putting pressure on my arms and on the ring, she could move me where she willed. She pushed me down the trail on my toes with my ass popped up because the strap was up my crack. As she forced me downthe trail, she had another strap of leather that she lashed my buttocks with as I walked down the trail. It was painful with my cock pulled down between my legs banging back and forth every step I got more engorged than it ever had been. Another strapping across my backside as I pranced along. "I am going to teach you a lesson for trespassing on my property, you will wish you never came here." I was beginning to wish that already. " I am sorry," I whined at her, " I will leave right now if you let me go", I whimpered. "SHUT UP!" She yelled an strapped my butt with the strap three times quick and hard stringing me bad. She would whip me and I would try to walk forward thinking that was what she wanted me to do, then she would tug back on the strap pulling my cock almost all the way back to pointing backwards, slowing me down. I think she want to go slower so that she could strap my buttocks more. It hurt, but for some reason I was very aroused by the whole thing.
Soon we came to the top of a small incline and there was a small house and a big barn. Pushing me towards the barn, she tugged me around so she could get ahold of the latch on the door. I heard the hinges squeak as the door opened, she then pulled me into the dark of the barn backwards, then spun me around once inside and pushed me forward until I ran into a hitching post that hit me about at the waist, she bent me over the post, she then connected my binding to a rope that was overhead and pulled up on it holding me bent over the post, strapped up like a horse, she tied off the rope and I was completely immobilized, with my arms tied and the same strap connected to my cock ring probably with a big brass clip that you connect to a horses halter. My wrists were bound and the strap went down to a clip that she had connected to my cock ring behind my balls. A light was switched on and I could see the inside of the barn with all the tack hanging on pegs on the wall. I looked up and could see the pulley with the rope through it keeping my bindings tight and me on my toes. My cock was pointing almost straight down and most likely purple by now, it was so engorged!
She walked around in front of me so that I could see her for the first time. She was short thin and wrinkled old gal but quite strong, obviously from handling horses all of her life. I begged her to let me go as she walked over to the tack on the wall and pulled a riding crop down with about a 2 inch square folded piece of leather on the end of it. I said nothing as I was afraid of getting spanked more. My cock started to go limp, but was no where near limp enough to get loose. She noticed it too and went to a cabinet and opened the door pulling out a tin of Bag Balm. Getting a generous portion of it and rubbing it on both of her hands, she walked around behind me and started messaging my shaft and scrotum, pulling down and squeezing me and working the balm into my skin, making me even harder straining against the rings to the point were it hurt but the pleasure kept making it harder still until the point that I thought it was going to explode. I was about to cum and started to moan, "This is the beginning of your lesson". She stopped milking me and picked up the riding crop and took a swing at my hind quarters. I could hear the crop wooshing through the air and a load snap as the leather square slapped the inside of my left butt cheek flicking ever so slightly the back of my balls. I screamed out loud and she swung again. Five times she swatted the inside of my ass with the strap up it. She moved to the other side and did the same on the right cheek, just on the inside part of the cheek and occasionally flicking my ballsack with the two inch square piece of leather attached to the four foot long stiff but flexible rod with a handle. She was a pro at it, I had forgotten about my prick as my ass stung like hell. My cock starting to soften again from the whipping, she started messaging my genitals again, tugging down in the same milking motion, bringing it back to life and another engorged session. Pumping up and down on my shaft and squeezing my jewels. She worked me to the point of cumming again, very close this time, but now she backed off and full on slapped the back side of my nut sack with the riding crop. I screamed in pain and ecstasy as I came harder than I had ever in my life. I pranced around and cried like a little girl. She grabbed my shaft again, she pumped me again milking the white stuff in long hard gasms that seemed to last for seconds at a time. I could not stop the urge to thrust my pelvis which tugged more at my cock extenuating the orgasm. I could hear my load hitting the hard dirt under my feet. When it finally ended I slumped over the post in exhaustion still strapped up like a stud horse. Sweat dripping from my brow and my cock still trying to squirt, oozing the last bits of siemen. "We aren't done yet there buck," she said and got another copious amount of balm an started in on me again. Masssging and tugging, pulling it down and milking it as if it were a big horse cock (that's what it felt like at the time). It was painful beyond belief, but just as pleasurable, in a way like I never felt, it grew again, bigger and bigger. She worked it hard a methodically until it was huge and throbbing. Again she picked up her crop and whipped my already stinging ass and balls. I was in. almost a trance now as she did her work, I actually spread my legs so she could smack the inside of my cheek. she whipped me with 20 swats this time, the weird thing was I could feel myself climaxing again just as she stopped. She pumped me again for a moment then stopped just short of me cumming again. Off she went to the tack wall bringing back a thin leather lace, she pulled on my balls and wrapped it around them about ten or twelve times and tied it in a bow, my nutsack was tight, rubbing them for a moment then going back to pumping my shaft until I was about to scream and cum. She worked me over until I could not hold myself, at that moment she took her middle finger and flicked my tight strapped up nuts. That put me over the edge, the orgasm climaxed squeezing hard and long, pumping over and over with another load cumming out, it was strained though as there was not as much cum this time. I am pretty sure that it was harder than the first time, I could feel the knob on my cock flexing bigger with every pump my tied up balls tried to push out. Collapsing again over the post in exhaustion, body limp from the primal stimulus. I passed out.
Being abruptly woken up with a cold bucket of water followed by a couple of sharp straps across my ass is something that I never want to experience again. Dripping wet and shaking, hanging by leather bindings, exhausted and on the edge of tears she untied the rope and relieved the pressure and grabbed the back of my straps, turned me towards the door and said, "MARCH"!!!!. Knees knocking I walked back toward the door and out into the night we went. "I don't want you coming back to my property. again". This was followed by a strap across the buttocks again, making me jump foward tugging on my swollen member still engorged but not hard, just big, slapping back and forth between my legs keeping it huge.
When we got back to the stump where she captured me, she picked up my shorts that were left on the ground and put them under her arm. She removed the clip from my ring, releasing me from the bottom and then my wrists. My arms dropped to my side, and I could hardly stand. One more swift whip from her riding crop, I jumped just out of reflex and tried to turn around, she was already gone. She had taken my shorts! I could not go back and get them from her, who knows what she would have done to me then? I was resigned to making my way home naked from the waist down except for tennis shoes. My swollen cock in a set of rings that I could not get off from being so swollen and all slicked up and shiny with bag balm. How was I going to get home, and if I even got there how would I get my house, the key was in my shorts. Had to think about it for a while, I can certainly make it most of the way home without being seen, what the last couple hundred yards though peoples yards and around their houses. I live in a duplex there was a little lady 65 years old named Isabel, she was always nice and I had given her my extra key in case she needed to get in for an emergency, well, this was one of them. I negotiated my way through the woods and to the edge of the development. No cars coming I snuck from property to property hiding behind cars and corners until I got to Isabel's back door. It was dark back there and I hoped it would stay that way. I drew in a deep breath and knocked on the door. there was a pause and then you could hear steps coming. I was so tired that I was leaning against her house with one arm, hanging out in all my glory with my brass cock ring on, purple and swollen, she opened the door a little bit to crack to see who was there, "ISABEL", I said in a strained voice, "Please shut off the light." she opened the door for she recognized my voice, the first thing she did was look down at my crotch, her eyes got big as coffee cups. I wasn't sure, but I thought I saw a little curl up of a smile on her lips. "What happened to you?" she asked. I slid inside her doorway to get out of the light, " I need your help Isabel, " my voice was obviously shaking, I slid into her kitchen and sat on a yellow vinyl chair with my legs spread because my cock and balls hurt, she looked directly at them and could not take her eyes off of them. She was such a sweet old gal, always wanting to help. "Who did this to you sweetheart? You poor baby, that looks like it hurts, let me make some tea and get you a cold washcloth. " She went over to the sink and ran the water to cool it of and got a nice big kitchen towel and wet it under the fawcett and rang it out. She turned and started the burner under the water for tea.she always seem to have something for me,, I mean she had a thing for me, she would often answer the door with hardly anything on and show me her nipples through her nightgown. She always talked softly to me, I must admit, she was pretty good looking for 65. She returned with the towel and gently put it on my tortured member, it was like heaven having the cool towel on it, the swelling seemed to start subsiding a little bit, I leaned my head back against the wall and closed my eyes.
"I have never seen a young man so big before, what are you wearing down there anyway? " I was so embarrassed and humiliated, I figured I might as well tell her everything, since I was letting it all hang out in her kitchen, so I told her the whole story over a cup of Earl Gray. She sat and listened to the whole story intently looking into my eyes , the problem was she knew my parents and all my aunts and uncles, my auntie owned the duplex, now I was sitting in her house with a big throbbing cock in a cockring with a cold towel on it. She picked up the towel and looked at me again. "My you are a big one, let me get some aloe for you and get you out of that contraption! " Putting the cold towel on it again she disappeared into the house to get some aloe. " Isabel, I was just looking for my key so I can get inside my place."
"Nonsense, you need tending to, besides, you don't want me to tell your parents do you?" Grinning while she said that I was red with embarrassment, I felt my prick shrivel a bit more, " Now let me take a look at it honey," pulling the towel away. She picked up the leaf of the aloe plant that she had laid on the. table, squeezing all the gel out of it she rubbed her two hands together evening out the aloe in her hands and reached down gently massaged the aloe into the skin, the cool of it felt so good, the problem was that I was getting big again and I could feel the ring tightening up. "My, that is quite the jewelry you have there! I don't think I have ever seen anything like that before." I was still surprised at myself for being so calm, normally I would have freaked out if she saw me naked before. Although she had tried to many a time beforehand to view me. I caught her once peering in the window, when I asked what she was doing she said she thought she something flash in the window. Now she was massaging my genitals and I was starting to enjoy it as she had such soft hands. I opened my eyes and looked down, she seemed to be enjoying it as much as I was. I asked for the key again and thanked her for her hospitality. " Oh it is no problem honey, I am glad to help. I am not going to give you back the key until I get what I want, just come in and lie on the couch."
Now another old lady had me, this time there were no bindings needed, I don't think I could have survived the embarrassment of her telling my folks about this.
"Now I am going to get what I have always wanted from you ever since you moved in. " She said it in a way that was innocent and old fashioned. It was a bit cute, I took her advice and got up from the chair and walked into the living room with my dick banging back and forth, I realized that my ass was still stinging when I laid down on the couch. I closed my eyes and Isabel came over and sat on the floor next to me and kept slowly and carefully massaging my cock and balls. Normally I am about seven inches long, but I noticed when I looked down at myself, my red cock with a big purple knob was about 8 and 1/2 inches with all the action it had seen during the night. Isabel started talking to me, "Listen my big strapping buck, I want you to put that thing in my and give me a good fucking, it has been so long since I have been mounted by a man."
"Isabel, please don't make me do this, we are neighbors." "You'll do it or I will tell your parents and auntie what happened tonight." Well I decided at that point that I did not want to suffer anymore embarrassment from anyone that I knew. "Alright then," I said, "How do you like it?" "Anyway you want to give it to me honey." I was feeling a bit of energy coming back so I got up and stood in front of her, she kept her hand on my shaft as I did it. I turned her around at the shoulders and marched her around to the back side of the couch, she seemed to like me taking control of her. I bent down and grabbed ahold of the bottom of her nighty and lifted it up over her head. She had about D sized boobies that hung down from the years and stopped in the middle of her tummy. She had big long hard nipples that I reached out and gave a good pinch to, lifting up her tits a little an letting them flop back down on her belly. "OOhh" she said, I took her and spun her again and bent her over the back of the couch. Her titties swung down and almost slapped her in the face. I spread her legs and reached down and touched her pussy. It was soaking wet from the excitement, it had been a long time for the poor old girl.
I lifted my cock and pressed it against her, she moaned as it spread her lips and I entered her slowly, the head of my cock entered her and she let out a little moan. I worked it back and forth a little to let her get used to it and to get my shaft wetted, then I started to penetrate her with my overly engorged cock that got harder and harder with every thrust. As I entered her deeper and deeper she moaned louder and louder until I was all the way in and could feel. my knob on her back wall. She shuttered and quivered as I held it all the way in. "Oh my God you are so big!" She said. Normally I was not that big, but under the circumstances I understood how she felt, I felt big to me too! I slowly started to move my hips back and forth with her wailing now out loud. Her titties were swinging back and forth so I bent over and reached down and cupped her big breasts and pinched her elongated nipples at the same time. She let out a loud coo and I started to really work her over, holding her down with my upper body and cupping and pinching her, she had no way out as I slammed my groin into her ass which quivered with every slap of my pelvic region. She cried out in ecstasy with every thrust as she had not been pleasured like that in so long.
Time had slipped away from us and the sun was starting to rise, I kept at her for quite some time as she took every bit of me she could. In my condition I was a little numb down there so I kept plugging her for at least 45 minute. The sweat rolled down my brow and her body glowed with perspiration. She came a number of times and I could feel the pulsations of her pussy squeezing my cock over and over as well as the screams she let out.
Isabel was a close friend of my auntie and they socialized frequently. So much so that that when my auntie Ingra came over she just came in without knocking. They would sit and have tea together. Well this morning was a morning that Ingra came over and walked in the door! This made Isabel freak out and she jiggled and twitched around trying to get out from under me. This excited me to no end and I felt a climax coming. so I held her down while she squiggled and thrust my cock all the way to the hilt and came really hard in her filling her with cream while my auntie stood there with her mouth gapping open watching. I held Isabel there and squirted all that I had into her before I let her go and pulled out. My engorged cock slid out and bounced up and down a little from the motion. I turned and looked and my auntie Ingra, who was starring at my big wiener for about 30 seconds as Isabel stood and regained her composure and was looking for her nighty. My auntie finally turned around and left without saying a word. Isabel was worried about what she would think, I told her not to worry and not to say anything about it to her. Ingra most likely told my parents about what she saw, I came to the point where I did not even care. I actually like boning that old gal, it was actually one of the best fucks that I had ever had.
I asked Isabel if that was what she wanted and needed, she was so happy to have been pleasured like that, but I could tell she was a bit embarrassed of being caught. I really enjoyed it too, and for the next couple of months she would come over to my apartment or I to hers and I would make sure that I was wearing my cock ring because she had grown fond of it. I was a twenty year old man fucking a sixty five year old lady in every position that you could think of. Since the cat was out of the bag with my auntie, we didn't see any harm in it. She would come over and catch me masturbating and tell me how bad of a little boy I was and just sit on my dick and bounce up and down or squiggle her ass back and forth while we watched TV together. I would always cup her tits and hold them up while I pinched her nipples, she would always coo and moan while I did it. One night I took her to the tree farm and told her before we left to wear a dress with no undies. I took her to the stump and lifted her dress, pulled down my shorts, she ben over and put her hands on her knees, I entered her from behind again and fucked her until we both had a good cum together. I was excited by the fact that the other little old gal might come back, but I am sure she did not want to get involved with what was going on, if she was watch, and I am sure she was. Sometimes when Isabel was not in the mood, (which was pretty rare) she would have me sit on a little wooden stool in the kitchen and have me masturbate for her while she had tea. I always wore my cock ring and she always seemed to enjoy the show. I have to admit, I enjoyed it more and more as the days wore on.
I would be at work sometimes, and all I could think about was getting home to give Isabel a good servicing. I would pull up in my old Chevy pick up and she would open the door as I was going into my apartment. She would ask me to come over and get my mail. That was just her way of saying, "I am ready for you to give me another one of those fuckings!" I would go change into some shorts that were easy to remove, slick it up a little with some Vaseline, usually by the time that I went over I had a raging hard on that made my shorts poke out in front. The lady across the street was raking her yard one day when I went over to see Isabel, she noticed the tent, she stopped raking for a moment an stared. I went inside and had Isabel bend over and put her hands on a chair, I mounted her and slid it all the way in slowly, she moaned loudly as I did it, as I slid it in and out and commenced pounding her she yelled, Oooh, Ooooh OOOOOh! louder and louder until she was about to cum. Then she yelled at the top of her lungs, "FUCK ME, FUCK ME, FUCK ME HARDER!" I stuck it in to the hilt and wiggled back and forth. When she came she went OOOOOOOOOOOOHHHH UH, UH UH in little short grunts. It wasn't long after that I filled her pie full of cream. We washed each other and put our clothes back on, when we did she opened the curtains back up. I then realized that the window was wide open. Going back to my place, the woman who was raking her yard stood there and smiled a big grin at me from ear to ear. I was embarrassed again.