My first time with Jack
Introduction:
It was unbelievable
Not sure how to start this.I want to tell the true story of how I spent my first night with a guy…a guy I met in a hotel bar. I had never been with another guy in my adult life. I am a healthy, middle aged guy who works out all the time, is reasonably good looking, and has a strong sex drive. I have been married and have children but now I am single and have been for five years.
This story begins I guess with a relationship I had with a girlfriend from long ago who had a particular fondness for anal sex. She would come time after time always wanting me to hold off coming as long as I could. Back then we didn’t have drugs like viagra, so I had to do everything I could to keep from coming inside her ass, which was so soft inside. She knew how to contract on my dick and would ride me while I was deep inside her. While it felt great for me, she was over the top with ectasy and would typically come more than once as I thrusted my cock inside her. I always wondered how she came without me stimulating her clit. It lead me to experiment with my own anus when I was alone.
First, I must tell you that she really enjoyed douching herself before we had anal intercourse. Once she was clean she would ask me to watch and she would fill her anus with hot water with a hose attached to the shower and would let out deep moans as she let the water rush from her backside.
So, one time when I was alone, not dating anyone, and feeling really horny I decided to try douching myself and seeing if I could fit a cucumber I had into my ass. I had a shower pic that allowed me to fill my anus with hot water and though I was a little grossed out at first, I kept at it and got myself completely clean. I greased up that cucumber with some vasilene and began to try and insert it into my ass. It took a while but I finally got the huge ten incher inside me. I was on my back, legs spread, and began to ride up and down on it, going faster and deeper with each thrust. It felt unbelievable. I started to stroke my very hard seven inch throbbing cock and had one of the most amazing orgasims ever…it lasted for a couple of minutes as I kept slowly humping it, pretending I had a huge cock inside me.
That was just the beginning of my anal fixation. I never thought I was gay or anything but I began to fantasize having an affair with a guy. I have dated women all my life and always will but I started to imagine what it might be having sex with another guy. When I was out of town I would go to adult stores and go into video booths that showed both straight and gay videos. I would get so hard watching two guys fuck and suck each other that I would search the dildo section for a big 10” hard cock that I could take home and fuck myself with. I admit that I did not ever want to be caught with it which was why I always waited until I was on an out of town trip. It got so that every time I went away, if there was an opportunity, I would spend hours fucking myself.
Lately I have taken my fixation to another level. I joined an online dating service that included a gay section. You could post pictures and videos of yourself on the site and try to find a match. I listed myself as a bi-sexual guy looking for another like minded male. I knew in my mind what I was looking for. I began to take pictures and videos of myself naked and riding a big dildo. I am not very hairy, have great legs and a pretty nice body so I got a lot comments and emails from guys wanting to hook up. I never showed my face, not wanting to ever let anyone recognize me and find out my secret desires. I could fuck myself for hours, pounding large dildos, the bigger the better. It never hurt, it felt unbelievable. I began to look at gay sites, looking for videos of two lovers sucking and fucking each other. I was especially fond of certain guys like Brent Corrigan…if you know who he is you know hot he was.
My love life was still hetro. I knew that I never wanted my two kids to find out my secret so I had to be careful and pick my times. I am getting horny just writing this. I began not to care about thinking whether or not I was gay, I knew I would always want the company of a woman, but I really wanted a real guy. More and more I wanted to feel a real man’s cock inside me, wanted to feel him unload his sperm into me, wanted to lick and suck him, even began to think about what it would be like to kiss him passionately while he was thrusting himself deep inside of me. My orgasims were really intense. I had to make a move so I began to frequent gay bars when I was out of town.
The gay scene kind of turned me off, I didn’t relate to the overt swishiness of most of the guys. I wanted an athletic guy about my size…and I knew he had to be hung. I would not compromise on that.
So, one weekend I was away on business and was staying in a downtown hotel in Baltimore. I was finished work and decided to go look for an adult store and buy a gay video and huge dildo so I could go back to my room and fantasize about a gay encounter. I found one and purchased the goods. On the way back to my room I stopped in the hotel bar for a glass of wine. I should stop and tell you that I loved to smoke pot and that whenever I would fuck myself I would get stoned…it intensified everything, especially my imagination. I smoked a “J” before I went out and was still very high and extremely horny when I sat down at the bar. There were ten or so people there, a few women and five or six men, one of whom was sitting alone. He was dressed in bluejeans and a designer t-shirt, and he had a nice build. I guessed him to be about mid-thirties. I sat down next to him and started up a casual conversation. We both were sport fans, he was a huge Philly guy (I was an unabashed NY giant and Yankee fan)and we talked sports. He was buzzed when I sat down and I brought him a couple of beers. Conversation got around to sex and I found myself becoming attracted to him. I was getting really aroused but did nothing overt enough to let it on to him. But then it happened. I excused myself to get up and go to the men’s room. I was hard as a rock and trying to hide it. When I got up I brushed against his thigh and I knew he could feel my manhood. It sent shivers up me. I caught a quick look at him and he looked back at me and laughed. I quickly went to the restroom, wondering what he could have found amusing. I can’t begin to tell you how horny I was getting and how bold I was beginning to feel. But I figured that I would probably just go up to my room and pleasure myself like I always did
When I returned to the bar, Jack, that was his name, was still there. I sat down and told him I was on my last glass of wine and would be hitting the hay. He said he would be doing the same. As we were finishing up, I felt a sudden urge to touch him. I figured I would never see him again so who cared. I slid my hand over onto his lap and slowly rubbed his crotch. He didn’t push my hand away and in fact moved his hips ever so slowly so as not to attract too much attention. I was over the top aroused but nevertheless pulled my hand away embarrassed. He then casually reached over and very discretely rubbed the inside of my thigh. I was wearing shorts and when his hand touched my bare leg I knew that this might be my first gay encounter.
I told a white lie and said to him, “Jack, I’m not gay but I do it with guys from time to time, any interest?” He nodded yes and we made plans to hook up. I told him my room number and said to give me a half hour.
I went straight to my room, smoked another “J” and went into the bathroom to douche myself. My heart was beating a mile a minute. I dressed in an undershirt and shorts with no underware on. I let my bulge stand out, actually I couldn’t help it if I wanted. Then the knock on the door came. I had the lights out but the trickle of light through the curtains lent the room to a sexy atmosphere. When I opened it Jack was also wearing shorts and a t-shirt. I think we were both hot as could be.
Jack entered and he came right up to me and put his hand over my crotch and began to rub me. Oh my God!!! Then he put his other hand around my neck and pulled me close, so close that I my face was inches from his. He kissed my lips ever so lightly and we pressed our bodies close together. Jack asked if I was sure about this. I was almost too hot to answer but I nodded and said sure! I turned from him and walked over the king sized bed. We were both hot and breathing hard. jack then said to me, “I have a secret to tell you. I am gay and I really live in Baltimore. I just broke up with my boyfriend and was feeling lonely. I didn’t want to go any gay bars because I knew I would run into guys I know and I am not in the mood to talk about Jimmy, my ex. When I met you in the bar I was just looking for casual conversation but, you know how one thing leads to another…Anyway, I find you attractive and when you reached over and touched me first, I thought this could be cool!!! So here we are.”
My next move was to lie back on the bed and pull him to me. We were lying side by side facing each other and he put his arms around me and we began to kiss, deep French kisses, intertwining our tongues and we grinded our hips rubbing our cocks against one another. I was living my fantasy. I pushed him away and reached for his shirt which I pulled over his head. I said, ”Jack, lie back and let me undress you.” He helped me unzip his pants and I pulled them down kissing his nipples and stomach and finally the tip of his large and very thick eight inch dick. This was the first time I had ever done this but I felt like I was a pro because of the fantasies I had when I was alone and making videos and fucking myself.
I put his cock in my mouth and began to suck on it, licking the underneath of his shaft and his balls. He was shaved and smooth and I couldn’t get enough. I wanted him to come in my mouth and I kneaded his balls with my hands and passionately kissed, licked, and sucked his throbbing cock. We began to get into a rhythm and I could feel him getting more and more into the moment. He was thrusting his manhood up and down inside my month. It was so tasty and not hard like my dildos but rigid and soft to the touch. I was making love to him and it felt like he was really liking what I was doing. He shouted” Oh my, don’t stop, I’m coming!” and he started to shake and lifted his hips high in the air. I took him in my mouth as far as I could and he began to shot his load into me. I took it all and we spent the next ten minutes together, me licking every bit of his sperm and caressing his shaft and balls.
I fell back, and just laid there. He was so handsome, his body perfect. I wondered what would come next. I knew that I wanted to get fucked by him. He asked if I liked him coming in my mouth and I told him “Oh yes!!! It was unbelievable!!” He said to me, “let’s make love to each other, I want to be inside you!” I answered by pulling him to me and kissed him on his neck, his ears, and then put my tongue into his mouth. He pulled away and started too undress me. When we were naked together on the bed he rolled over on top of me and began to kiss me again, grinding his hips into me. His hands were all over my cock and I said to him, “Jack, I have wanted you inside me ever since I met you.” He rolledme onto my stomach and he put his hands on my ass and began to play with my hole. He wet his fingers and gently forced one into me. I moaned and as he was going in and out with his finger he reached under me and stroked my cock and balls. His tongue then found my hole and I couldn’t believe how great it felt, his long soft tongue darting in and out of my hole. I was beyond hot as he lifted up and placed the tip of his rock hard penis in my ass. I pushed up against him. It was easy to penetrate me as I had fucked myself so many times before with large dildos. He was lying flat on top of me as I pushed up against him and slowly let him inside me. It felt so much better than anything I could have imagined and I grinded up against as hard as I could. We started to get into a rhythm together and he was pounding me hard. I said, “Jack, roll me over I want to see you!”
I was now on my back and Jack took me, completely. I spread my legs and offered myself up to him. As he knelt between my thighs, he leaned down and kissed me deeply. I took his cock with my hands and put it inside me. I could not contain myself as he pushed all eight inches into me. We stopped and just laid there for a long time. He was all the way in me, and my legs were wrapped around his waist. My arms were holding him tight and we began to make out like lovers, our hips moving together, him slowly making a circular motion with his cock all the way in. I could feel him in me, so hard, but soft at the same time. We were both breathing harder, and began to move together, in perfect motion. I whispered to him, “I love you Jack” and we started to come together. I could feel him pulse inside me, squirting his load into me. I was in a complete frenzy and my cock started spurting come all over our two bodies. “Ahhhhh, my god Jack, don’t stop!!”
We stayed locked together for it seemed like an eternity. Both still hard. Both sated. Both knowing that we just did something really special together. I knew then that my days with a dildo would be a lot fewer. I now knew how great the real thing felt. And I knew that whenever I came to Baltimore, Jack and I would be lovers, no matter who else was in our lives. We made love another time that night and again in the morning. We were intertwined during the night as we slept…my balls and cock throbbed the whole time. It was truly an unforgettable trip.
This story begins I guess with a relationship I had with a girlfriend from long ago who had a particular fondness for anal sex. She would come time after time always wanting me to hold off coming as long as I could. Back then we didn’t have drugs like viagra, so I had to do everything I could to keep from coming inside her ass, which was so soft inside. She knew how to contract on my dick and would ride me while I was deep inside her. While it felt great for me, she was over the top with ectasy and would typically come more than once as I thrusted my cock inside her. I always wondered how she came without me stimulating her clit. It lead me to experiment with my own anus when I was alone.
First, I must tell you that she really enjoyed douching herself before we had anal intercourse. Once she was clean she would ask me to watch and she would fill her anus with hot water with a hose attached to the shower and would let out deep moans as she let the water rush from her backside.
So, one time when I was alone, not dating anyone, and feeling really horny I decided to try douching myself and seeing if I could fit a cucumber I had into my ass. I had a shower pic that allowed me to fill my anus with hot water and though I was a little grossed out at first, I kept at it and got myself completely clean. I greased up that cucumber with some vasilene and began to try and insert it into my ass. It took a while but I finally got the huge ten incher inside me. I was on my back, legs spread, and began to ride up and down on it, going faster and deeper with each thrust. It felt unbelievable. I started to stroke my very hard seven inch throbbing cock and had one of the most amazing orgasims ever…it lasted for a couple of minutes as I kept slowly humping it, pretending I had a huge cock inside me.
That was just the beginning of my anal fixation. I never thought I was gay or anything but I began to fantasize having an affair with a guy. I have dated women all my life and always will but I started to imagine what it might be having sex with another guy. When I was out of town I would go to adult stores and go into video booths that showed both straight and gay videos. I would get so hard watching two guys fuck and suck each other that I would search the dildo section for a big 10” hard cock that I could take home and fuck myself with. I admit that I did not ever want to be caught with it which was why I always waited until I was on an out of town trip. It got so that every time I went away, if there was an opportunity, I would spend hours fucking myself.
Lately I have taken my fixation to another level. I joined an online dating service that included a gay section. You could post pictures and videos of yourself on the site and try to find a match. I listed myself as a bi-sexual guy looking for another like minded male. I knew in my mind what I was looking for. I began to take pictures and videos of myself naked and riding a big dildo. I am not very hairy, have great legs and a pretty nice body so I got a lot comments and emails from guys wanting to hook up. I never showed my face, not wanting to ever let anyone recognize me and find out my secret desires. I could fuck myself for hours, pounding large dildos, the bigger the better. It never hurt, it felt unbelievable. I began to look at gay sites, looking for videos of two lovers sucking and fucking each other. I was especially fond of certain guys like Brent Corrigan…if you know who he is you know hot he was.
My love life was still hetro. I knew that I never wanted my two kids to find out my secret so I had to be careful and pick my times. I am getting horny just writing this. I began not to care about thinking whether or not I was gay, I knew I would always want the company of a woman, but I really wanted a real guy. More and more I wanted to feel a real man’s cock inside me, wanted to feel him unload his sperm into me, wanted to lick and suck him, even began to think about what it would be like to kiss him passionately while he was thrusting himself deep inside of me. My orgasims were really intense. I had to make a move so I began to frequent gay bars when I was out of town.
The gay scene kind of turned me off, I didn’t relate to the overt swishiness of most of the guys. I wanted an athletic guy about my size…and I knew he had to be hung. I would not compromise on that.
So, one weekend I was away on business and was staying in a downtown hotel in Baltimore. I was finished work and decided to go look for an adult store and buy a gay video and huge dildo so I could go back to my room and fantasize about a gay encounter. I found one and purchased the goods. On the way back to my room I stopped in the hotel bar for a glass of wine. I should stop and tell you that I loved to smoke pot and that whenever I would fuck myself I would get stoned…it intensified everything, especially my imagination. I smoked a “J” before I went out and was still very high and extremely horny when I sat down at the bar. There were ten or so people there, a few women and five or six men, one of whom was sitting alone. He was dressed in bluejeans and a designer t-shirt, and he had a nice build. I guessed him to be about mid-thirties. I sat down next to him and started up a casual conversation. We both were sport fans, he was a huge Philly guy (I was an unabashed NY giant and Yankee fan)and we talked sports. He was buzzed when I sat down and I brought him a couple of beers. Conversation got around to sex and I found myself becoming attracted to him. I was getting really aroused but did nothing overt enough to let it on to him. But then it happened. I excused myself to get up and go to the men’s room. I was hard as a rock and trying to hide it. When I got up I brushed against his thigh and I knew he could feel my manhood. It sent shivers up me. I caught a quick look at him and he looked back at me and laughed. I quickly went to the restroom, wondering what he could have found amusing. I can’t begin to tell you how horny I was getting and how bold I was beginning to feel. But I figured that I would probably just go up to my room and pleasure myself like I always did
When I returned to the bar, Jack, that was his name, was still there. I sat down and told him I was on my last glass of wine and would be hitting the hay. He said he would be doing the same. As we were finishing up, I felt a sudden urge to touch him. I figured I would never see him again so who cared. I slid my hand over onto his lap and slowly rubbed his crotch. He didn’t push my hand away and in fact moved his hips ever so slowly so as not to attract too much attention. I was over the top aroused but nevertheless pulled my hand away embarrassed. He then casually reached over and very discretely rubbed the inside of my thigh. I was wearing shorts and when his hand touched my bare leg I knew that this might be my first gay encounter.
I told a white lie and said to him, “Jack, I’m not gay but I do it with guys from time to time, any interest?” He nodded yes and we made plans to hook up. I told him my room number and said to give me a half hour.
I went straight to my room, smoked another “J” and went into the bathroom to douche myself. My heart was beating a mile a minute. I dressed in an undershirt and shorts with no underware on. I let my bulge stand out, actually I couldn’t help it if I wanted. Then the knock on the door came. I had the lights out but the trickle of light through the curtains lent the room to a sexy atmosphere. When I opened it Jack was also wearing shorts and a t-shirt. I think we were both hot as could be.
Jack entered and he came right up to me and put his hand over my crotch and began to rub me. Oh my God!!! Then he put his other hand around my neck and pulled me close, so close that I my face was inches from his. He kissed my lips ever so lightly and we pressed our bodies close together. Jack asked if I was sure about this. I was almost too hot to answer but I nodded and said sure! I turned from him and walked over the king sized bed. We were both hot and breathing hard. jack then said to me, “I have a secret to tell you. I am gay and I really live in Baltimore. I just broke up with my boyfriend and was feeling lonely. I didn’t want to go any gay bars because I knew I would run into guys I know and I am not in the mood to talk about Jimmy, my ex. When I met you in the bar I was just looking for casual conversation but, you know how one thing leads to another…Anyway, I find you attractive and when you reached over and touched me first, I thought this could be cool!!! So here we are.”
My next move was to lie back on the bed and pull him to me. We were lying side by side facing each other and he put his arms around me and we began to kiss, deep French kisses, intertwining our tongues and we grinded our hips rubbing our cocks against one another. I was living my fantasy. I pushed him away and reached for his shirt which I pulled over his head. I said, ”Jack, lie back and let me undress you.” He helped me unzip his pants and I pulled them down kissing his nipples and stomach and finally the tip of his large and very thick eight inch dick. This was the first time I had ever done this but I felt like I was a pro because of the fantasies I had when I was alone and making videos and fucking myself.
I put his cock in my mouth and began to suck on it, licking the underneath of his shaft and his balls. He was shaved and smooth and I couldn’t get enough. I wanted him to come in my mouth and I kneaded his balls with my hands and passionately kissed, licked, and sucked his throbbing cock. We began to get into a rhythm and I could feel him getting more and more into the moment. He was thrusting his manhood up and down inside my month. It was so tasty and not hard like my dildos but rigid and soft to the touch. I was making love to him and it felt like he was really liking what I was doing. He shouted” Oh my, don’t stop, I’m coming!” and he started to shake and lifted his hips high in the air. I took him in my mouth as far as I could and he began to shot his load into me. I took it all and we spent the next ten minutes together, me licking every bit of his sperm and caressing his shaft and balls.
I fell back, and just laid there. He was so handsome, his body perfect. I wondered what would come next. I knew that I wanted to get fucked by him. He asked if I liked him coming in my mouth and I told him “Oh yes!!! It was unbelievable!!” He said to me, “let’s make love to each other, I want to be inside you!” I answered by pulling him to me and kissed him on his neck, his ears, and then put my tongue into his mouth. He pulled away and started too undress me. When we were naked together on the bed he rolled over on top of me and began to kiss me again, grinding his hips into me. His hands were all over my cock and I said to him, “Jack, I have wanted you inside me ever since I met you.” He rolledme onto my stomach and he put his hands on my ass and began to play with my hole. He wet his fingers and gently forced one into me. I moaned and as he was going in and out with his finger he reached under me and stroked my cock and balls. His tongue then found my hole and I couldn’t believe how great it felt, his long soft tongue darting in and out of my hole. I was beyond hot as he lifted up and placed the tip of his rock hard penis in my ass. I pushed up against him. It was easy to penetrate me as I had fucked myself so many times before with large dildos. He was lying flat on top of me as I pushed up against him and slowly let him inside me. It felt so much better than anything I could have imagined and I grinded up against as hard as I could. We started to get into a rhythm together and he was pounding me hard. I said, “Jack, roll me over I want to see you!”
I was now on my back and Jack took me, completely. I spread my legs and offered myself up to him. As he knelt between my thighs, he leaned down and kissed me deeply. I took his cock with my hands and put it inside me. I could not contain myself as he pushed all eight inches into me. We stopped and just laid there for a long time. He was all the way in me, and my legs were wrapped around his waist. My arms were holding him tight and we began to make out like lovers, our hips moving together, him slowly making a circular motion with his cock all the way in. I could feel him in me, so hard, but soft at the same time. We were both breathing harder, and began to move together, in perfect motion. I whispered to him, “I love you Jack” and we started to come together. I could feel him pulse inside me, squirting his load into me. I was in a complete frenzy and my cock started spurting come all over our two bodies. “Ahhhhh, my god Jack, don’t stop!!”
We stayed locked together for it seemed like an eternity. Both still hard. Both sated. Both knowing that we just did something really special together. I knew then that my days with a dildo would be a lot fewer. I now knew how great the real thing felt. And I knew that whenever I came to Baltimore, Jack and I would be lovers, no matter who else was in our lives. We made love another time that night and again in the morning. We were intertwined during the night as we slept…my balls and cock throbbed the whole time. It was truly an unforgettable trip.
