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Click hereMost guys fantasize about being with a girl when they jack off. I did too, but I also fantasize about being with a guy a lot. Thank god for the internet; knowing other guys were thinking the same thing made it seem all right. Having just turned 18 I wanted to do more than just fantasize. I did not know exactly what I wanted to do or how far I wanted to go. I was worried that I was fantasizing more about playing the girl's role then the man's. I knew I wanted a man to teach me, to show me, to be the aggressor, to seduce me and treat me like his whore.
I was 5' 8" 140 pounds. Swedish parents on both sides so I was very blonde and very fair skin with no body hair. I was very slim and had a very sexy ass. I had dated a few girls in high school but never got too far with any of them. I looked a lot younger then 18 and got carded even going into r rated movies, so taking a date to the movies was out.
I read a lot of erotic fiction and spent hours at night in chat rooms, never using my real name or location. I looked at bi and gay porn and masturbated a lot fantasizing it was me doing what they were doing in the porn pictures or movies. I started to look at gay and bi personals ads on websites and the Craiglist. I got extremely turned on by some of the postings. Especially ads of older guys looking for younger partners.
After awhile I decided to post my own ad on one of the sites. It read. "Chicago area, 18 yr old looking for experienced older guy to learn from, needs to be clean, disease free, discreet, and patient".
In the morning I checked my email and was surprised to find lots of emails answering mine. Half just said my ad was hot and gave no more info then that. Many were from guys around my age looking to meet for sex. That wasn't what I wanted. I found one that I really liked. It was from a 46 year old married man named James who lived in Chicago and wanted to introduce me to the bi scene. He wrote that he understood the importance of having a good teacher for my first time and would love to be my mentor. He left his email address and I hoped he would be hearing from me soon.
I replied to his email immediately and asked him to meet me in a chat room that night. He met me there and we went private. He was married and his wife Terry was cool with his bi actives as long as he was discreet. About 10 minutes after we started chatting on line he asked if I wanted to call him on the phone. His typing was not great so I called him like he asked me to.
He had a great voice, very deep, and very sexy! We talked about everything, sports, politics, life in general, then finally getting into sex. He wanted to know what our next step was. I told him I was not sure how far I wanted to go or how much I wanted to try. He said that was ok with him, he was not pushy and that it had to be right for both of us. He suggested we meet somewhere in public first, talk some more, and see how things progressed. I was fine with that and very excited.
We decided to meet at a Mc Donald's near my house the next day. He sent me a picture of him, just his face so I could I recognize him. I went to the Mc Donald's early and nervously sat nursing a coke wondering if I was doing the right thing. I loved the tingling feeling in my cock and balls from just thinking about him touching me there.
I saw James walk in and order a coffee. He sat down at a table near me and started looking around. He was even better looking in person then he was in his picture. He was very manly looking, masculine, handsome and looked self-assured. He was tall, a good head taller then me, 6'2" or 3", which was a turn on for me.
I walked over to his table and sat down across from him. I was nervous as hell. When I sat down and he looked up, smiled and said, "You must be Bob." I nodded yes. We talked for a while and he made me feel more comfortable with every word. He suggested we go for a walk, it was a beautiful day and there was a park nearby.
We walked around the park talking about everything: my mother, his wife, my college, his job. Finally, the conversation got around to sex. He suggested we go some place private to talk. He offered that we could go; to his car, his house, or any place I liked. I said I would like to look and maybe just touch each other to start with. He nodded and suggested we go over to an area in the park that had dense bush and trees where we wouldn't be seen. We walked over to where we were deep in the trees and got off the path to make sure no one could see us.
After an awkward silence, he smiled and asked whether it was ok for him to show his cock. I nodded and he pulled his pants down revealing his beautiful long, thick and extremely hard cock. I never saw a cock that big in person before. He was 8 inches maybe 9 and very thick with a mushroom shaped head.
I decided to drop my pants too exposing my 6 inch cock. He reached over and took my entire shaft in his large hand and started stroking me. I began to tremble from the wave after wave of tingling sensation that moved over my body like a blanket. It was as if James had read my mind about the role I wanted to play. The way he moved his hand on my small cock was like he was playing with a clit instead of a cock.
I looked up in his face and then closed my eyes. He read what I wanted and kissed me on the lips hard, he kept slowly stroked my cock while I was locked in his kiss. His tongue darted in and out of my mouth and it felt great. The chills from his kiss and him stroking my cock went up and down my body like an electric charge. He had me almost convulsing with pleasure. I reached for his cock and started to run my hand up and down his long shaft. After a few minutes of kissing and jerking each other, I broke his kiss and did something I wanted to do ever since I first fantasized about male sex. I surrendered to him completely and let my feminine side out, completely out.
I slowly sank to my knees and came face to face with the massive head of his throbbing cock. I wrapped my hand around it and stroked it a few times then stuck my tongue out and licked the tip. His precum was hot and wet with a musky taste and the smell was beautiful. I opened my mouth and took his head in, I slowly massaged it with my tongue, and to my joy, I heard him breathe deeply, I look up and made eye contact with him, he smiled and gently rested his hand on the back of my head. I started to take more of his cock into my mouth I got about half way down to shaft until I felt I couldn't take anymore then I slowly withdrew until the tip was between my lips. I stroked my hand up and down his thick hard shaft in unison with my mouth. I never sucked a cock before and hoped James was enjoying my first attempt as much as I loved sucking him.
I could feel that he is getting close to climax, I looked up, with his cock in my mouth, and saw the look of pure lust on his face, getting more turned on by the way he looked. He ran his hands through my hair and groaned loudly. I felt his balls become rock hard to my touch. He firmly grabbed my hair and pulled my head onto his hard cock I knew he was close. I felt myself gagging as he pumped my face onto his cock. I gagged more as he began to send load after load of his hot spunk deep into my throat. Instead of pulling back away from him, I let him use my mouth to empty his load in.
I squeezed his cock with my hand to make sure I had all of his cum and then swallowed. James removed his cock from my mouth and told me on how good I was for a being a first timer. I smile and welcome his praise. He pulled me up to my feet and kissed me again full on the mouth with his tongue darting in and out of my wet cum soaked mouth that had been on his cock only seconds before. He put his hands on my bare ass and pulled me into him, French kissing me as he did.
I was still hard, slowly grinding my cock up against his naked leg. James stopped me and let me know we needed to leave before someone saw us. That brought me back to my senses. We both pulled up our pants and straighten ourselves out. We walk back into the main park, and walked back to Mc Donald's hardly saying a word. We did not go to back in the restaurant but walked straight to his car.
He asks if I wanted to go home with him or we could do some more in his car if I wanted. I was too horny to answer and just opened the door and got into his car. While driving he motioned me over close to him. He unzipped my pants with his free hand and got my cock out and stared playing with it. I was incredibly turned on knowing he found my cock a turn on. He did not ask me again about where we were going. We drove to his house, all the while he teased my cock like it was a clit. He would get me close to cumming then stop. He wanted me to save my cum for some reason.
Soon we were at his house and we went inside. He asked whether I wanted to use the bathroom or have something to drink. I was too horny for any of that. He took me by the hand and lead me upstairs to the bedroom. The room had a woman's touch, which reminded me that he was married. He must have read my mind and said it was ok she was out but it didn't matter anyway even if she was home. She was cool with his having young guys there.
We stood facing each other by the side of the bed. He moved over by me and we started kissing each other again. Soon his hands were all over my body and starting to pull my clothes off. I let him, and soon I was down to my under pants. He pushed me down roughly onto his bed with my legs hanging over the edge. He leaned over me and kisses me again running his hands over my chest and stomach sending shock wave after shock wave thru my body. While he was kissing my mouth, he reached under the elastic of my under pants and started playing with my cock.
His kissing moved to my neck and ears. He gently worked his tongue down to my nipples biting them and sucking on them. With his every kiss and bite I felt a jolt of electricity shoot from my nipples to my balls. I felt his hot breath on my stomach as he moved his face down to my crotch. He ripped my under pants down exposing my cock. He used his hand to guide my little cock into his mouth and he expertly begins to suck it. He buried his nose in my short blonde pubic hair as he took all my cock in his wet hot mouth. I feel his tongue move around my cock and I rolled my eyes back in ecstasy.
He expertly used his mouth, hand and tongue to bring me to a climax like I never had before. Afterwards we kissed again and I tasted my cum in his mouth which started getting me hot again. He laid down next to me and we kissed some more. James was the aggressor and had me in his strong arms as he French kissed me again and again. He stopped kissing me and stood up and stripped himself naked. I couldn't take my eyes off of the show he put on for me. My lover getting naked for me!
He picked up a tube of KY lubricant and brought it over by us. My heart started to race as it dawned on me what he wanted to use the KY for. He stood over the bed and looked down at me with total lust in his eyes. "I am going to fuck that virgin ass of yours" I heard him say. He wasn't asking my permission, just telling me what he was going to do to me. I just nodded yes. I was still lying on my back at the edge of their bed, he lifted my legs and pushed them up till my knees were on my chest.
I held my knees where he wanted me to and he bent down and slowly licked my balls and kissed my spent cock. Then he moved his attention towards my cherry ass hole. I felt his tongue probing my tight virgin hole. His rough wet tongue sent shivers from my asshole right thru to my cock and balls. Then I feel his KY lubed finger replace his wet tongue at my virgin opening. He kept gently rubbing the jelly in my ass slit with his finger. At first he was only able to get the tip of his finger in my cherry bottom. He added more lubricant, and inserts his finger again this time with more ease, he swirls his finger around and I start to relax my ass muscles. I began to breathe deeply and slowly and felt another finger slip into my ass. It felt so good! I wanted more and begged him with my eyes for it.
He stood up and moved over to get his cock into position to penetrate my ass. He looked down at me and I looked up at him my eyes begging for it. He ran his big thick cock up and down my ass cheeks rubbing the lubricant in as he did. I felt the tip of his mushroom cock at the entrance to my virgin hole. For a moment I want to scream No, beg him not to put it in me but I didn't. I felt his cock start to enter my male pussy. I relaxed and slowly felt his cock slide into me, the big head popped in and past the tight muscles around my entrance. I let out a long pleasurable moan as he slowly pushed his thick shaft deeper into me, stretching my tight virgin ass muscle around his big cock. It seemed like an eternity until I feel his balls touching my ass cheeks. It hurt, but I felt so good knowing I was taking all of his beautiful cock in my male pussy. I thought to myself, I am making my man happy by giving my cherry ass to him.
I can feel his cock deep inside me, he held himself inside me for a while to let me adjust to the fact that I have lost my anal virginity. He slowly withdrew his 8 inches of cock until just the tip is inside me making me feel very empty inside. "Please, don't take it out" I say in a soft voice. He did not plan to take it out until he had his hot cum buried deep inside of it.
He thrust into me hard and fast, hitting me in a special spot in my male pussy. I felt a wave of pleasure start from that spot to my small cock. He started to fuck me in long smooth strokes making sure all of his cock went into me before he withdrew almost all of it. I felt a wave of pleasure with every stroke of his cock. I reached up, touched his chest and rubbed my hands over his firm body. I clamped my legs around him as I felt my climax build. Then I grabbed his ass and spread my legs so he could fuck my ass as deep and hard as he wanted.. He picked up the pace and pumped his cock into me hard and fast. Sweat formed on his brow and he let out loud groans and moans of pleasure as he continued to pound his cock into me no longer caring that it was my first time.
I soon was having another climax. James's belly rubbing against my cock made it happen. My ass tightened as my cock unloaded onto our stomachs and chests. It must have felt like a vice on his cock because it sent James over the edge. With a deep thrust, I felt his trembling cock swell and unload his cum deep inside me. He fell forward and we kissed like lovers until his cock softened and slid out of me. In the afterglow of my climax I felt so alive, so pleased with myself, happy that I made him cum so hard. I wondered if he came that hard with his wife Terry and hoped that he didn't.
We had made quite a mess on the bed and ourselves and so James told me to jump in the shower. I stood up and walked to the bathroom. I felt his eyes on me, appreciating my beautiful round ass, and smooth hairless legs. I felt his cum running out of my ass down my legs. The sight of his handy work must have turned him on. As soon after I got into the shower he came in with me, running his soapy hands over my young body. I again submitting to him and I bent over ready for my second fucking, his hard cock was quickly buried inside me, thrusting in explosive passion. The hot water ran on my back. I felt light headed because my head was down. On the verge of passing out I was engulfed in pleasure as I had another climax. Soon after my climax, I felt James unloading his hot cum inside my male cunt again. I almost collapsed but James held me up. He lifted me in his strong arms and carried me to his bed where he had taken my virginity.
I must have fallen asleep because when I woke up, I was alone and naked on the bed . My ass hurt but not as bad as I thought it would. It was still dripping cum from the fuckings James had given it. Even with the pain I felt so wonderful knowing James had enjoyed my male pussy and that he would again and again. He made me his fuck slut today, and loved it!
I’m through reading Literotica. You have a serious issue in publishing the last response to cumming out.
I'm a 58 year old I've fucked several younger guys, for most of them, it was their first time, and some screamed or cried when I slipped my thick 8"cock in their ass. The best I ever had was the son of a casual friend, a boy with Down's Syndrome. He was about 14 at the time, and a slighty chubby, hairless body. I was gentle with him, hugging and kissing before sodomizing him. He took in my cock all the way , fucking me back and making little grunting noises, absolutely the tightest and most willing fuck toy I ever had, Then when I climaxed and pulled out, he went down on me and licked my dick clean. When we had finished and were having an after-sex cuddle. I asked him where he learned to suck and fuck like that, he said his Dad and older brother fucked him frequently, starting when he was about 7.
Liked it very much (4.5 Stars).....The story includes the two meeting at McDonalds and then going to a nearby park (for a well described suck) My similar experience a few years ago when I sucked off a teenage McDonalds worker in my car at the rear of the parking lot after he go off work and the restaurant had closed. He SAID he was 18 but I suspect he was much younger and had very little experience. He was quite short and thin, with small cock about 5" erect..almost "dainty" and called me "sir" or "mister" (We didn't exchange names)..After that first time we met 3 more times and on the 3rd encounter, he sucked my 8"dick while I stuck my finger up his ass. I regret to to this day that I didn't fuck him, because I feel he was "ready", still, he was a lovely, sweet boy and I often wonder if he is still sucking old cocks.
First hook up can be scary but I got lucky
I was hooking up with a 19 year old who loved an older daddy type like me with a big thick penis. He enjoyed sucking my big cock!