My name is Gerard and I am twenty-two years old. What happened to me happened five years ago. I had just turned seventeen when I went to visit my neighbour. She is no longer one of the youngest, but despite her forty-five years, she is still very pretty. As a teenager, I often masturbated while fantasising about her in the most horny way. I found and still find older women much more attractive than younger ones. For me, though, it is a condition that they still look delicious and really feminine. But usually it is something about an older woman that attracts me, her clothes, her smile, her hair, her breasts or her legs in tights. With my neighbour, Jenny, my ideal was complete.
She is a very intelligent woman with a beautiful body. Long hair, always smiling, a pair of big breasts and she always wears skirts with stockings underneath. She usually wears thick high heels, because she is a small woman, but a woman with the necessary courage. I went to see her that day because my parents were away for the weekend, and as I don’t like to cook, she let me have a bite to eat with her. She was divorced, so she had nothing against a bit of company. Everything was just right for me that day, she was wearing a blouse, skirt, tights and my now favourite stiletto heels.
When she bent down, her bottom was tight in her skirt and when she walked, her breasts moved back and forth. So I was very happy to help her wash the dishes. She wore a delicious perfume, and sometimes we would play together, and I would rub against her. Then we would sit in a chair, where she would smoke a cigarette, and we would chat and watch television. Suddenly she had to go to the toilet and tried to continue the conversation from there. I didn’t understand any of it, of course, so I went into the hall to stand opposite the toilet.
I just assumed that the toilet door was closed. But when I entered the hall, my eyes fell out of my head in amazement, and my dick had an immediate reaction, it went hard in no time! She had left the door open, so I could see her sitting on the toilet. She had pulled her skirt down to her stiletto heels and I now saw that she was not wearing pantyhose, but real nylon stockings! I heard her pee clatter into the toilet and she smiled at me adorably. I was mortified and apologised, but she said it was no big deal. I wanted to leave, but what was unfolding before my eyes would not let me go. I tried to concentrate on the conversation, but I couldn’t. The urination had stopped.
I could see her pubic hair and pussy.
She immediately stood up so that I could see her pubic hair and pussy. My mouth fell open in surprise and excitement. “I don’t suppose you’ve ever seen that before?” she said, smiling defiantly. “I have,” I replied. I explained briefly that I had met a girl at a local party, that after the usual tonguing, I had fingered her pussy, outside, behind a wall, while she jerked my cock. We hadn’t gone any further because we were too scared to get fucked. She asked me if the girl’s pussy was nicer than hers. “Hm, I said, she had shaved her pussy smooth and her labia were also thinner. And she hadn’t pissed, but she was still as wet as you are now”.
She laughed hornily and then said, “Oh, my pussy is starting to drip, don’t you want to dry it off so you can feel for yourself how wet it is.” “Um, what do you mean?” I stammered. She said, “Just because this stays between us, just wipe my pussy dry.” “Okay then. “I took some toilet paper, bent down and slowly wiped her pussy. Meanwhile, I put an arm around her waist to support me. She stroked my hair. “Go on if you want,” she said, “you’re obviously horny, and I know from experience that a man always has to come when he’s horny.” I asked if she was serious and she confirmed again. I threw the piece of paper into the pot behind her and started stroking her pussy. My first blow job, and even then with her, it seemed like a dream.
But it wasn’t. I tasted her urine and it made me even hornier. She started fidgeting with my trousers. She opened the zip and unbuttoned my trousers. “Anna,” I said, “I don’t have any experience of eating pussy. Am I doing it right? And where is the clitoris on a woman?” “You’re doing quite well,” she said, “look, you have to pull my labia away with your hands. Yes, pull it, it doesn’t hurt, on the contrary. And now you have to run your tongue through my pussy and along my labia. Suck my pussy juice. Sometimes hard, sometimes soft, you have to respond to my panting and moaning. Give me your hand. I gave her my hand, which she guided to a bud in her pussy. “That’s my clit, horny boy. If you want to get a woman’s pussy really wet, if you want to turn her into a horny romper, you have to lick this bud and massage it between your fingers.
So if you want to make it a fun night with me, you’ll have to work my clit now, because I’m going to be in heat like a bitch. You bitch!” I didn’t let her tell me twice, I was horny as hell and wanted to do anything with her. She seemed to want it too. I licked her pussy and rubbed her clit between my fingers. Anna, who was sitting on the edge of the pot, pulled my t-shirt off. She started panting and moaning. I asked her to pull her feet up. This allowed me to remove her skirt and blue thong, giving her more room to spread her nylon-clad legs. It was the greatest moment of my life: Anna, sitting on the pot, wearing only her blouse, her nylons down to her thighs and her stiletto heels still on. I bit her while my cock was dripping with pre-cum, and she started to pant more and more. She was getting really horny, becoming a bitch in heat, as she had said herself. I stood up and asked her, “Anna, we have been alone all evening and all night. That’s why I’m asking you if you want to be my sex teacher tonight. It will stay between us, it’s our secret. Will you teach me everything?” “To teach you everything, I will definitely need a whole weekend. But I really want to teach you everything. I’m horny, you made me so horny, now I have to keep my promise. Do you have the whole weekend?”
“Yes Anna, I have time, I…” I didn’t get to finish my sentence because she started to tongue me. I pulled her off the pot and flushed. She walked ahead of me into the kitchen on those horny stiletto heels. I put her on the table and asked her if she had any condoms. She did, she said, but she was on the pill, and as she hadn’t fucked since her last period last month, and I’d never fucked before, she suggested we do it without a condom. “Your cock in my pussy, without a condom, that gives much more pleasure.” I continued to caress her, inserting a few fingers into her pussy and stroking her nylons with my other hand. She had lovely long legs. She gasped and moaned harder, grabbing her blouse with her hands until her breasts were almost out of the blouse. I increased the pace of the pounding, occasionally licking through her pubic hair, sucking up all her pussy juices. She moaned louder, she started screaming and jerking.
Her pussy juice was now pouring out of her cunt. Then she came! She screamed and wrapped her legs around my head. Wow, what was that, this was not like the girl from the party. She was emotional, panting and even crying. I kissed her all over. “It’s been so long,” she said, “and you did it so well. You made me come greatly. Now I’m going to spoil you. Have you ever seen breasts other than your mother’s?” I nodded no. “I have seen my mother’s, yes, but they are not as big as yours, I think. But of course I’ve seen breasts on TV and stuff.” “And in porn books for sure,” she laughed, “have you ever bought a porn book? One of those disgusting, rancid ones where girls and women, dressed in horny lingerie, nylons and stiletto heels, let you look at their cunts with a smile?”
But now you can see real breasts.
“Yes, I admitted, and more than once. And afterwards I always jerked off, sometimes as many as four times in an hour.” “All men do that. It’s a sign that you’re healthy. But now you can see real breasts. You can touch them, hold them, pull the nipples, everything.” She undid the buttons of her blouse, took it off and I saw her black lace bra, straining under the weight of her breasts. If my cock had come at that moment, I would have shot off immediately. I fumbled with the clasp and after a few seconds her bra opened. Real breasts at last! I weighed them in my hands, my God, how heavy they were. And oh so beautiful. Her nipples stuck out hard. “Play with them, my boy”. I licked her breasts and her hard nipples, hesitantly at first, then with increasing confidence. She stroked my hair and massaged her pussy with her other hand. “So student,” she said after 15 minutes, “if you take off my heels and nylons, you can fuck me right here on the table. You can do anything to me.” “I would very much like you to keep your nylons on.
And your stilettos too. I think it’s awesome to see you.” “Ooooooh, naughty boy, is that your big fantasy? That’s your fantasy, kicking women in nylons and high heels. Shall I keep these on or would you prefer me to change? Go to the wardrobe in my room, there are many more heels. Just pick a pair, and I’ll give you a tip: take the open shoes, then you can still lick my toes if you feel like it”. I couldn’t believe my ears. What a horny bitch she was. I took off her high heels. “You’re naked and the floor is cold, my neighbour said, put them on if you can and then try to walk upstairs with them.” My feet were bigger, but not by much, and these were open heels anyway. I tried, and my cock turned bright red with excitement. “Now you’re horny,” she said. I took a step forward and almost fell over. But I thought I was really horny myself. My next steps were hesitant while she was still laughing excitedly.
From her wardrobe I picked out a pair of black patent open court shoes with stiletto heels of up to six inches. I came back to her, still tripping over her heels. “Put them on, my dear, you clearly have taste.” I put the heels on her and fastened the straps, not forgetting to lick her toes as well. I kissed her all over, fingered her pussy, then tried to crawl on top of her. Finally I was on top of a woman, a real woman. She caressed and kissed me, her hard nipples scraping along my chest. She used her hands to guide my cock into her pussy. I pushed gently and then it was in. Oh, how wet and warm her cunt was. Slowly and quietly, just like in the films, I started fucking her. Now we were both moaning. I asked her if I was doing it right and she told me it was perfect. Her legs were in the air, I could see her nylons and stiletto heels perfectly. We were both sweating and I still had her hot heels on my feet.
Despite the fact that I was almost exploding with lust, I managed to keep my cum inside me for another five minutes. But then I felt my orgasm coming on. Come on, fuck me!” she screamed, “fuck my cunt blue, squirt your cum into my cunt!” I screamed, thrusting even harder and then it came! I squirted her cunt full of cum. I squirted for over ten seconds, it was amazing. I kept pumping, I wanted to give her what she deserved: an orgasm. “Don’t tire yourself out. I’ll come and sit on your cock,” she said. Now I had a perfect view of her full breasts. I kneaded them as she rocked on my cock. “Slap them! Slap my breasts! Squeeze my nipples!” I slapped, softly at first, but silently harder and harder. She screamed, rocked harder and squirmed again. She came again. Still on top of me, I stroked her back. After a few minutes she calmed down. “Let’s have a bath,” she suggested.
We walked into the bathroom, our heels clicking on the floor in unison. It was horny and the evening was still young. She filled the tub and I took off her heels and took off her stockings, licking them all over. She sat down in the tub and I took off my heels and joined her in the tub. We caressed, kissed and washed each other. “I have to pee,” I said. “Do it here,” she said, “it’s just a little urine, nothing bad, and besides, it can be great. Okay, she said. I stood up and started to play with my still stiff cock. She watched excitedly until suddenly a yellow stream came out: I peed in the bath. She stood up and gasped at the jet. She drank my urine! It was so cool! We got out of the bath and dried each other off. We’re going to fuck again, she decided, “I’ll show you how”. We went into her bedroom. “Here I have something, especially for you!” she said as she took a pair of black nylons with a garters out of the cupboard. She allowed me to put them on. “Can I have your heels?” she asked, “then you can try on my heels.
Would you like some nylons too?” “Is that what turns you on, Anna, transvestites?” “No way,” she said, “give me a real man, one with balls, filled balls. But you can always show your feminine side with me.” I thanked her for the nylons anyway. She took a dildo out of her cupboard and handed it to me. She asked me if I knew what she wanted to do next? I told her that I might have to fuck her from behind, but that I didn’t know if I wanted to fuck her in the pussy or the ass. “What would you like to do?” she asked. I’ve already had your pussy. If you think you can have my thick cock in your ass, and if you feel like anal sex of course, I would love to do that.” She said nothing, took my cock and put it in her mouth. She sucked it and pulled on it while massaging my balls with another hand. When, after ten minutes, I indicated that I was about to come, she stopped quickly and said, “I think it will fit. You have to turn the dildo on and insert it into my pussy.
Then you have to lick my ass and insert your cock carefully. Carefully, because I have to sweat for a while. I have two big things to do. You know this position is called the doggy-style? It’s a dirty, disgusting, but horny position. The man dominates the woman, the woman lets herself be overpowered. The man sets the pace, he can fuck the woman to pieces. Now I am really your bitch, you understand, your bitch in heat. I am your horny bitch, your bitch. You have to make me feel like a whore. I am a whore, I am your whore. I need to feel pain, but most of all pleasure. You can spank me on my bottom and you can scream at me all the words you read in your horny porn magazines. Just remember that it makes me horny.
I sat behind her, stroking her nylons and licking along her suspenders. She reached for the edge of the bed. She had quickly put on her bra as the weight of her breasts had become too heavy. I switched on the dildo, it began to vibrate and move. I stroked it along her pussy, then pushed it into her cunt. She wriggled hornily. I licked her asshole. “Deeper, deeper, your cock should slide in easily. Put your tongue in my hole”. I licked as deep as I could. When my saliva ran out of her ass, I stopped. Meanwhile she was moving to the rhythm of the dildo. She was getting ready for a fantastic orgasm. I placed my cock in front of her ass and gently pushed it into her arse, thrust by thrust.
She screamed and writhed. After about five minutes my cock was all the way in. I paused for a moment, pushed the dildo that had slipped out of her pussy a little harder, and then began to move slowly. “Fuck me! Fuck me in my ass!” I did and began to fuck her arse. How amazing this woman was. So I told her. “So Anna, you like this delicious, huh, horny bitch. I’m going to fuck your ass, you won’t be able to say porridge anymore. I’m going to fuck you all over!” I was embarrassed by these words, but she actually encouraged me, saying ‘yes’ to everything and calling me an animal from time to time. She was screaming and moaning, but enjoying herself.
Cum dripped from her pussy. I licked her nylons and slapped her bottom. I almost came in her ass. And how! I unhooked her bra and cupped her heavy breasts with my hands. What hard nipples! I squeezed them and thrust incredibly hard. I came! The cum was literally pouring out of her ass. I was completely out of this world, in seventh heaven, and kept thrusting. She pulled away from me. “My cunt, I want to come! I want your cock in my cunt!”. I turned her over, pulled the dildo out of her cunt and stuck my cock in. I put her nylon legs over my shoulders and started pumping, incredibly hard. I wanted to fuck her cunt all the way through! I wanted to make her come.
After ten minutes, that was it. She was writhing and screaming. I had to fight to stay in her cunt. After she came, we lay on the bed for another 15 minutes. Then she looked at me and said, “So that was lesson 1. I hope you enjoyed it. You passed with flying colours. But tomorrow we are going to do other horny things. I’m going to dress you up like a girl, so you can feel what it’s like to wear nylons. I think it’s really hot to rub your nylons against mine. I would like you to sleep here tonight. If you are still up for it in a while, you can fuck me again. It is going to be a great weekend, Gerard” Indeed it was a great weekend and it got even better.