First Time Fucked. SeXStoRY

This is the true story of the first time I was ever fucked by a guy: I started having gay sex when I was 18. My first experience was with a guy I met through a female friend with benefits while I was still in high school. He was not the first guy who fucked me in the ass. He did teach me how to fuck a guy in the ass with my cock though. He taught me the importance of holding back until just the right moment to cum. He also gave great blow jobs and taught me how to give them and how to swallow cum without gagging. I had sex with him and other men as a top for about 2 years in the early 1990's. Fast forward to about 1992. I was attending a small business college in Des Moines, Iowa where I lived at the time. I rode bike to and from school. One day on the way home I was going down a hill on the trail I was riding on. As I applied the brake to slow my descent the brake malfunctioned and the pad wedged under the rim, stopping the front of the bike instantly, throwing me over the handle bars superman style. Thankfully I hit the grass and dirt, but chest first as I lifted my chin as I made impact with the ground as to protect my face. As I hit and bounced my heavy back back, which had slid back while I was in the air flew forward and smacked me in the back of the head, pushing my helmet over my forehead and eyes. This area of the trail is an access for other trail users with parking. Another guy who had just finished a run saw this happen to me and came running over to see if I was alright. I was trying to get up but could not see and my chest hurt as it was very hard to breath. He told me to lay still in case I was seriously injured. He didn't push and hold me down, but put his hand on my back to calm me. I calmed down and didn't move, except to put my arms under me to hold up my upper body while I lay there on my belly. It was then I realized why I could not see. I rolled slightly to my side and to move my hand and arm up so I could take off my helmet. He saw this and helped. I again tried to get up some more but he told me to hold on. He started asking me questions, who I was, did I know what day it was, etc. He asked if anything hurt to move or if I lost any feeling anywhere. I answered his questions and told him I can feel everything. He helped me sit up and take the back pack off. At this point I had caught my breath and it did not hurt as bad to catch my breath. So I stood up and looked back at my bike. Which was about 10 feet from where were standing. I checked it out and it was not in ride-able condition. Keep in mind this was before cell phones. Even so no one was home to come help transport me home. He asked where I lived and I told him another 5 miles on the south side. He lived just a mile or so away and told me I can come with him so I can get cleaned up and call home when someone was going to be there. I was a mess after hitting the ground. He had a truck, so we loaded my bike in it and went to his place. When he said get cleaned up I did not think he meant I could use his shower. He did and I changed into the regular clothes I wear at school as I had bike clothes on at the time. While I was in the bathroom I noticed some gay porn magazines in an old antique magazine rack. I didn't think anything of it, since I like gay sex too. These showed a lot of older men fucking younger guys though. While it turned me a bit I was in no shape to jerk off or have sex. After my shower I called home, but no one was there but knew someone would be home soon. He invited me to wait and talk with him. He told me what he does for a living and how old he is. He was 60 at the time, I was only 21. I decided to take a chance and brought up the gay magazines in the bathroom. He was not embarrassed or anything and asked if I like gay sex. I said I do. He asked what I do. I told him I like to suck, get sucked and fuck. He asked if I fuck bare back or with a condom. I stated I prefer bare back. It feels better for me and the other guy when I cum, but will wear a condom if the other guy asks me to. He then asked if I have ever been fucked. I stated no. He asked if I ever thought about letting a guy fuck fuck, I stated I had not given it much thought. At that point he advised I call home again. I did and someone answered. I told them what happened and that the guy who helped would bring me home. On the way to my house I asked him what he likes to do with guys. He told me suck, get sucked, get fucked and fuck. I stated I wish I was in the mood for sex. He advised better to wait until I feel better but invited me to call when I am ready. He dropped me at home. The next day I figured out he was right about waiting. I was very sore and bruised. It took a good week to feel better. Then one day before I left school I called him and asked if I can come over for sex. He said yes and could not wait. I arrived at his house. When he answered the door he was naked. He was beautiful. Nice, thick, uncut cock, it looked about 5 inches when soft. I had never been with an uncut man before and could not wait. I stripped naked and got down on my knees. But he wanted me to shower first. So I did. When I was done he was in his bed waiting for me. I got into bed with him and we started stroking each other. He then sucked my tits and squeezed my ass, then moved to my cock. I knew I would cum if he was half as good at giving a blow job as he was at sucking my tits and stroking my cock. I warned him I don't want to cum yet. He stated he wants to swallow it. He took me deep in his mouth. After a few pumps into his throat I emptied my balls and he swallowed every drop. After we lay there but i was disappointed it was over so early. He got up and so did I to get dressed. He said no, we were not done and stood there with his hard 8 inch cock before me. I went down on him taking as much as I could in my mouth. I discovered very quickly I loved the feeling of the foreskin of an uncut cock sliding up and down in my mouth as I performed oral sex on him. this turned me on so much I started getting hard again. He started moaning with pleasure. I knew he was getting close so I backed off. I wanted to control when he same. After a little while of bringing him to the brink and then backing off I finally let him cum in my mouth. He tasted great. His cum was thick and creamy with just a hint of saltiness to it. After we recovered from that he wanted me to fuck him, bare back. I got behind him, entered his ass and started fucking him. While I was fucking him I noticed he moves his ass like a woman does her pussy. He was squeezing his ass cheeks together, move back and forth, etc. This felt incredible as i have never had a guy do this when I fucked one. It did not take long for me to cum deep in his ass. After we both took a shower and I went home. After that we saw each other at least once a week. We would pretty do the same things sexually but did change it up on occasion. We even had a few 3-somes with other guys and even a few women. Then one day when I arrived for one of our hot sex sessions he brought up the magazines I first saw the first time I met him. He asked if I remember what was in them. I said sure, older men fucking younger guys and asked why. He then asked, since I have been with him if I thought about being fucked. I did admit I had thought about it. We talked about it for a bit. It was then I decided to let him fuck me and deflower my virgin ass but was worried it would hurt too much. He said not to worry he has a technique that is painless. Here is what happened: He had me lay on my back, legs together. He lubed the entrance to my butt hole. He told me he will talk me through the whole thing. He also said to control my breathing while he penetrates me. He said, when he tells me to, take a deep breath and let it out very slowly as he enters me and when I run out of breath he will stop s I can take another and breath out slowly as he penetrates me until he is all the way in. He straddled me and put his huge cock head right against my butt hole and pushed in a little to open my cheeks and hole just a little to make sure he would not slip out of position. I could feel the heat from his massive prick, it felt like it was blowing into my tight virgin hole. He told me to take a deep breath and to start letting it out. I did so. As I let it out he started penetrating me. First the tip of the head of his cock opened my hole and entered me. Then I could feel his entire hear in me. It felt intense, very hot, as in the physical feeling of heat, there was a lot of pressure, but no pain at all. He got about a quarter of the way in and i ran out of breath. I quickly took another deep breath and he continued to penetrate me. I could feel the thick veins on his cock against the inside wall of my rectum. i also felt ever ridge and bump on his cock. Soon he was all the way inside me. He stopped and did not move. He asked how I feel I told him there is no pain, just a lot of heat and pressure. He said when he fucks me he will only pull out as far as just before the head comes out and push back in and will continue this until he cums. So he did so. He fucked me, and fucked my virgin hole good. I could feel his foreskin move back and forth or in and out as he fucked me. That first time he was pretty steady. But I did indicate I was enjoying it by pushing back onto him as he fucked me. He increased his thrusts into me until he finally exploded his cum in me. It was the most intense and hottest thing I have ever felt to this day. After we were done I fucked him and we lay there in each others arms until I had to go home. After that we had sex at least twice a week. Our relationship continued until his company transferred him to a different state. I have had the pleasure of using the technique he used on me to deflower other virgin men. I may not be as big as my former lover, but before he taught me that technique, when ever I deflowered a virgin guys ass there was always pain. After I learned it there has not been.

first time fucked SeXStoRY

I was only 18 when i was used for the first time . i was watching a game that night so i was late for home . when i was in a hurry to catsh the bus i was attracted by someone who was walking in front of me . he had a femenine walk with flexible body and very tight jeans . he seemd like a girl from behind but he was bold than i recognized he was a man. so i slow down and followed him a little while from behind without taking his attention . i figured out thats he is a gay men ,i was turned on by his walk and his femenine style . he stopped in front of an appartment . he was living there , he noticed me walking toward him so he gave me a sexy look . i stopped and asked him about time . and protended that im waiting for a friend . iwant to fuck his tight ass so bad . he said that he will wait with me . we talked for a while then he invited me to his appart and wait there because it was freezing outside . i gladly accepted the invitation. we entered to this dark building and we tooked the stairs to rich his room on the 6th floor. he opened the door and we get in . we sitted on the couch next to each other .we talked a little then he started to kiss my lips so softly and waiting my reaction.i liked it so much so he invited me to his bedroom. i laid on his bed and we started kissing then i take off all my clothes and so was he . he had a great ass and huge shaved cock. he start to suck my cock and i enjoyed it so much it was my first time . i thought that the next step was to put my cock inside his ass and fuck him but he surprised me when he stood up on bed and put his big cock next to my mouth and wanted me to suck him. i was attracted by his big cock so i liked the idea and started to suck his cock . he f***ed it inside my mouth i felted . it was so hard and big to the point that i couldn't continue but he insisted . then he put in a doggystyle position and told me that i have a very sexy ass that was maided to be fucked and that he couldn't resist it . i told him that i was virgin but he told me thats is gonna be ok and that i will be a very sexy gay men with fuckable ass then he puted some lotion next to my asshole and started to put his finger inside my ass then he puted his cock slowly untill it was inside my asshole then he fucked me faster and faster . i felt good . and i was screaming like a reel slut .suddenly two of his friends were knoking on the door . he told not to get worryed then he returned and said to me thats two of his gay friends were visiting him and asked me if they could join us . i was thrilled by the idea . i accepted . they were to femenine gay men also. they tooked off all clothes and joined us . he returned to fuck me in doggystyle and one of them puted his cock in my mouth and the other was watching and playing with his cock then they switch roles . i was fucked by all the three of them the whole night and sucked them all . two of them came on the same time. the bold one came while his fucking me he come inside my asshole and the other when i was suking him so he came in my mouth the third one camed also inside my mouth . and i tasted his hot cum and make me swallowed . at that i was cuming also. it was a great sensation. i was like a bitch to them they fucked so hard and without mercy. it was late so he told me to spend the night. in the morning we changed numbers and i left not believing what just happened last night. he told that i was the perfect gay that every men want to fuck. i' ll never met him again .but i lived many other exiting experiences that you will never beleive . i will post other stories later. i hope you will enjoy my stories and excuse my english . i did my best.

First time out, first time fucked. SeXStoRY

I was looking good even if I do say so myself. Six inch black platform heels, black hold ups, the obligatory little black dress, long red wig and my fave faux fur jacket. I felt sexy, I felt like a slut and I wanted the world to see me. I hadn’t been out before but I had been building myself up for this moment for months. I had it all planned. Wait until dark, slip on my sweatshirt, tracksuit bottoms and trainers over my stockings and dress, stick my wig, shoes and jacket in my rucksack. I’d have to risk it in case anyone saw the make up but I figured it would be dark enough for no one to notice, especially if I wore my baseball cap low. I was excited and nervous but taking a peek outside realised it was now or never. I quickly locked the front door and slipped into my car. Within a minute I was off the drive and heading towards the park on the other side of town. It was late out and there wasn’t much traffic, but the nerves were building and I don’t think I would have noticed either way. I pulled up in a dark area of the park’s car park, not too far from the entrance but far enough away that I wouldn’t be noticed getting changed. I changed quickly, putting on my shoes, wig and jacket. Quick check in the mirror and I was ready. The first thing that hit me was the breeze on my legs. I had shaved them earlier and the sensation was electric. I could resist running my hand up my stocking clad legs. I could have been happy with that but I was determined to see this through. I gently eased myself out of the car trying to look as ladylike as I could just in case anyone was around. A quick glance around told me that there wasn’t and I quickly locked the car and headed for the park entrance. The click of my heels on the pavement excited me. It was turning me on to know I was making that sound. I continued into the park concentrating on my walking and swaying my hips. I’d practiced plenty of times at home but this was different and delicious. The sound of my heels as I sashayed through the gates was extremely erotic. I was so caught up in how much this was turning me on that I didn’t notice him until he stopped in front of me. “You haven’t seen a little dog around here have you?” he asked. I quickly looked him up and down. He was late 20’s about 6ft 1, athletic with short brown hair and very cute looking. “Er, no.” I replied in my best feminine voice. “Actually, if I’m honest I haven’t lost a dog. I just needed an excuse to speak to you. Hi, my name is Simon.” He offered his hand. I was quite sure what to do. I hadn’t planned on speaking to anyone. “Erm, hi I’m Sarah”. I’ve no idea where Sarah cam e from but it was the first name that popped into my head. “Hi, Sarah. What brings a pretty girl like you to the park late at night then?” Simon enquired with a twinkle in his eye. Before I was able to reply he continued “I saw you getting changed in your car and was curious but as soon as I saw your legs. I knew I had to speak to you.” “You saw me getting changed?” Shit! I thought I had been so careful. I was beginning to panic. “Don’t worry. I’ve always been an admirer of girls like you. Your secret is safe with me.” He must have sensed my panic. “In fact I’ve dated quite a few, but I have to say you are certainly one of the sexiest I’ve met.” I was a bit surprised by his openness but also flattered by his comments. I couldn’t help but blush. “Thanks, but I bet you say that to all the girls.” I was trying to be modest but I loved the attention. “Honestly it’s true. Here feel for yourself.” He took my hand and placed it on his crotch. I could feel his hardness through his jeans. He felt big and I could feel him getting bigger as I touched him. “Wow.” I let out an involuntary gasp. “See my cock never lies.” I had never felt another cock apart from my own and it was certainly bigger than mine and seemed to be getting bigger. I wondered how big it would get and what it would taste like. “Here, come with me.” He grabbed my hand and led me towards the bushes. We passed through a small gap and were suddenly in a small clearing surrounded by bushes and trees. He stopped next to a large tree and turned and kissed me. It took me a bit by surprise but I responded eagerly as his tongue explored my mouth. I could feel his hands trace their way down my back and rest on my ass giving it a squeeze. I was in heaven and let out a soft moan as our kiss continued. He pulled me into him and I could feel his hardness pressing in to me. My hands moved to squeeze his cock. It felt so good and so big I just had to see it. I started to unfasten his belt. He realised what I was doing a broke our kiss and to unbutton his jeans. I stepped back as his jeans fell down past his knees releasing his glistening cock. It was the biggest one I had ever seen and must have been a good 13-14 inches long. It looked so good I knew I had to taste it. I dropped to my knees in front of him with his cock pointing straight at me. Like a school girl unsure about licking her first lolly I stuck my tongue out to taste it. It was slightly salty but also delicious. “Why don’t you kiss it?” I heard him pant. I lent forward and gently kissed the tip of his cock. I hadn’t tasted cock before and was unsure what it would be like but here I was wanting desperately to fit it all in my mouth. I continued to kiss his cock enveloping his cock head in my mouth. I began to twirl my tongue around his cock trying to savour the taste of it. I must have been doing something right because I began to hear him moan and gently thrust his hips forward pushing his cock further into my mouth. His thrusts were gentle but were becoming more rhythmic. I had only ever sucked on a dildo before and it was nowhere near the size of Simon’s cock. I was worried I was getting out of my depth as he thrust more and more of his cock into my mouth. I slipped his cock out of my mouth and began to kiss along it’s shaft. I kept alternating between taking as much of his cock in my mouth as I could and kissing along his shaft. Although I was enjoying it, and judging by the sound of him so was Simon, I knew that I was also a little scared of trying to deep throat his huge cock in my mouth. Suddenly Simon lifted me to my feet. “That feels sexy babe but it’s your turn now.” He said turning me so I was facing tree with him directly behind me. He lifted the hem of my dress up exposing my panty covered ass. He started to fondle my ass and then I felt him move my panties to one side and start teasing my hole with his finger. I loved having my hole played with and Simon’s touch was electric. He stroked and caressed around my hole and suddenly I felt something warm and wet enter it. It took me a moment to realise that it was his tongue and he was literally tonguing my ass. It was heaven and I couldn’t stop from letting out loud moans and pushing back onto his heavenly tongue. “Oh, fuck babes that feels so good.” I said encouraging his tongue deeper into me. He was driving me wild. “Oh, god. Fuck me! Fuck me! I need you inside me.” If I had thought about it I would have had second thoughts about screaming that out but I was so turned on I just wanted to have him in me. “Fuck me Simon! Make me your slut.” I was caught up in the heat of the moment. Simon stopped tonguing my ass and stood up behind me. I could feel the heat of his cock pressing at my boy pussy. I began to push back hungry to get his cock in me. I had fucked myself with dildo’s before and regularly used a small butt plug on myself but nothing prepared me for the pain I felt as Simon’s cock head pushed into me. I screamed and Simon stopped pulling out of me. “Do you want me to stop?” He asked. “No!” I wanted his cock in me so badly. “Just take it slow so I can adjust. I’ve never had a cock as big as yours in me.” It was true but there was also some bravado in my words as I wasn’t sure I could take his cock. Simon worked his cock slowly into me, letting me adjust when the pain got to intense and get used to his monster. Eventually he was completely buried in me. I had never felt anything like it before. There was still a bit of pain but that was being replaced by a fullness and a feeling of euphoria than I had managed to fit him all into me. “You okay?” He asked. “Yes, just take it slow at first.” He began to slowly slide his monster in and out of me. The pain and concern quickly subsided as the waves of pleasure and lust for his cock I was feeling began to build. I started to push back encouraging him deeper into me and he responded by upping the tempo. “Yes, babes that feels so good. Fuck me hard make me your bitch.” The pain was gone and I was in pure ecstasy. “Faster babes. Fuck my little slut ass.” I wasn’t sure where my dirty talk was coming from but it had its desired effect as Simon began to really pound his cock into me. I braced myself against the tree to stop from falling over. “That’s it babes. Pound my tranny ass.” His cock seemed to grow bigger in me causing waves of pleasure. “Oh fuck.” Simon called out. He was really pound his monster cock deep into me and as he tightened his grip on my hips I knew he was close to cumming. “That’s it babes, cum in your tranny slut’s ass. Make me your bitch.” I had never been this turned on in my life but I was desperate to make Simon cum in me. Suddenly I felt his cock explode in me with spurt after spurt of hot fluid coating my insides. It sent me over the edge with pleasure and I’m sure I blacked out a little. Simon held his cock in me until I regained my composure. Eventually he went softer and began to slide out of me. “Wow. That was quite a show you two put on.” We both turned in the direction of the voice… To be continued.