Although when a child you have those moments you show your friend your dick and what not, this is my first real sexually experience with a another man. First off let me say I consider myself straight, although technically I have been with men so I guess that makes me bi even though those days are over with. However I always wanted to every since I think I was around 13. I was always curious about it but never acted on it other than masturbating.
When i got around 15 or 16 I started chatted on aim chat rooms that was m4m. I don’t believe that back then craigslist was around like it is today. When I was a senior in high school I was 17. That is the age I started sexually experimenting with both girls and guys which lead to the loss of my virginity from both. Early that year in the fall, I first lost my virginity to a girl. Then when spring came I finally decided to start looking into doing it.
I could not risk looking for someone I know out of fear that people would find out so I never even considering looking in that direction, which is why I chose to look at the aim chat rooms. Overtime, I would arrange meeting with men of all ages but I would end up ditching them by eventually not responding or just not showing up and never speaking to them again. I was absolutely petrified to do it; I thought I’d regret it and be known as a gay person; I was very conflicted with it. Eventually my courage and temptation rose to a breaking point: I decided to finally go through it and not be scared and back out for the 900th time.
After looking through the chats after a while, I ended up chatting with a man named Tim who was a 45 year old bisexual white male. I told Tim I was 18 so he wouldn’t get scared and not want to do it even though I was 17, I would eventually tell him this later in the future which he had no problem with. I saw his picture and let me say if i thought he was very ugly I not have done it, I wasn’t doing it with just anyone. Tim I believe worked for a sporting company or something in that ballpark and traveled a lot and lived in an apartment with a roommate if I remember correctly. I forget how long I actually talked to him but considering how scared I was, I would have probably of talked to him for a couple months stalling a lot.
Eventually I decided it was time, we talked for a while about where to meet, I believe he did offer his apartment but I believe I wasn’t comfortable enough thinking he was a serial killer or something. Eventually we decided to meet up in the library parking lot that was across the street from my high school. The day that we ended up doing this was on a Sunday and I know i cancelled about 4 times or more, I do remember that much. We set a time and waiting up to that time I was almost having a heart attack from the fear and anxiety of doing it. When the time to go to library was near, I left about 30-45 minutes early.
Although you probably already think that I was fucking stupid for doing this, I still had street smarts (I think so at least). I told him to park in the back so I parked further to the left of it that was crowded by cars so he wouldn’t see me. If I would have gotten a really bad feeling about it and backed out for the 900th time, I would do so. So I always had an exit strategy and some brains for this situation at hand. Eventually the time approached and the fear level was through the roof, I kept debating in my head whether or not to get out of there.
Tim was about 15 to 20 minutes late which I expected considering he lived further up in the main city of the county I lived in. While I was debating this Tim’s van drove in and parked in the back, it was a blue old 90s style van with a ladder and a spare tire that was attached to the back of it. When he parked I immediately pushed my car into drive and started to drive away saying fuck this and never talking to this guy ever again. Almost to the exit of the library I put my brakes on and turned back around and parked a little bit closer to the van but not noticeably. I was going through with this and I refused to wimp out and repeat everything again and most likely again after that. It was put up or shut up time and my temptation and curiosity reached a point where I couldn’t put it off any longer.
I sat there almost having a panic attack stalling for time. I remember how horrifying it was opening my door and getting out, I’ll never forget that feeling going through out my entire body. I put my keys in my pocket and left my cell phone and wallet locked in the car. Walking up felt so surreal as if I was having an outer body experience. As I walked up to the van Tim saw me and rolled down his window and I nervously said hello to him. Tim said hello and asked how I was doing which I told him I was good and then he told me to get in the passenger’s seat. Walking towards the passenger seat I felt like I was about to go into another a portal to another dimension. I opened the door and got into the passenger seat, and as if a portal had closed, so did my passenger door when I closed it.
Tim and I spoke for a few minutes and he then asked me to go sit in the back. In the back the blinds to the windows were all down and it had two separate car seats and a couch that could turn into a bed for traveling. I went to the back and waiting while Tim reclined the couch with a button in the van. I sat down with him and we spoke briefly and he then told me to lay back. I froze in horror as this was going on saying “oh my god” in my head 5000 times fast. After I lay down he started to unbutton my pants and pulled them down with my boxers following exposing the bottom half of myself. I was frozen in fear while I watched him put my penis in his hand and moved his mouth towards my penis.
My penis by the way is 7 inches cut and very thick with veins. I reacted by looking away petrified that this was about to happen, last thing I saw before looking up at the ceiling of the van was when my cock was entering his mouth. I said to myself in my head that it’s now happening for the very first time. It was incredibly having my dick sucked; I only had oral sex twice with two chicks. Technically when I was 9 or so I let a boy put my penis in his mouth for 2 seconds because he had always wanted to. I never really considering that my first time with a guy, I looked at it as your typical boys experimenting as child’s. After a while, I eventually started to watch in curiosity as his sucked my cock with determination. A couple of minutes later he stopped giving me oral sex and pulled off his shorts exposing his 5 inch penis which had a very large head. I rose up and stopped in hesitation at first, I took a deep breath and moved my head toward his crotch and put his cock inside of my mouth. I imagined how to give him oral sex only because I had a dick as well and I knew what felt good. While giving him oral sex he put both of his hands on my head and lightly pushes down on my head while moaning. I had told him before hand to not cum in my mouth, after a while I took his cock out of my mouth and I thought I noticed precum which I asked him. Tim replied its nothing don’t worry about it which I ended up wiping it off just in case and then hesitantly put it back in my mouth thinking that I wiped it all off in case it was precum. After a while Tim told me I sucked dick like i did it before and soon after that he told me to lie back down. Tim got up and turned around and started to his legs in between my face so we could start to 69 each other. On top with his weight and his cock in my mouth caused his penis to go further down my mouth and gave me less control of his cock. We sucked each other’s cock for a while and then Tim turned back around and told me to lie on my back. Tim proceeds to stick his tongue in my asshole and rim me for a very long time. During all of this, he eventually stuck a finger in my ass. Throughout doing this he would repeatedly tell me to relax as my asshole clinched hard against his finger. I believe that he put 2 fingers in my ass when I told him he could fuck me with a condom. I could see Tim contemplating this but decided against it because of the fear of the van shaking and letting everyone in the parking lot think people were having sex. Eventually Tim told me to turn back around and started to suck my penis again. After a very long time I could feel that I was going to cum. I told him I was cumming and the first time I came from oral sex was never again like that for me. I thought I was going to cum but feeling only got stronger and stronger. After about 45 seconds to a minute I told him loudly that I was cumming and I watched as my cock exploded inside of his mouth. My dick throbbed very hard and rapidly for about 30 seconds and when it finally stopped he took his mouth off my dick and spit my semen inside of a towel. Right after he did that it was like my sexually interest in all of this was gone and I was back to reality, I no longer wanted to do this. However, being a good sport I told him to jerk off and cum on my stomach. I took my shirt off and stared at the ceiling never once looking at him while he masturbated while he stood on his knees in between my waist while I was lying on my back. Eventually I hear a moan come out of Tim followed by a shower of very warm long strings of semen went all over my stomach. I never once looked down at it while Tim gave me the towel and started wiping it off. After that we both started to put our clothes back on and we awkwardly talked for a brief few minutes. Tim told me to give contact him on Aim again when I wanted to do this again which i replied that I would. After saying nice to meet you and good bye I then exited the back passenger door and returned back to the world that I lived in, like i was exiting a portal that just had opened up for me to do so. I walked back in complete shock that I had just done this, in my head I kept thinking that tomorrow is Monday and i will see everyone I know in my classes and that none of them would ever think that the day before I had sucked a cock, let alone the cock of a 45 year old man. After I got in my car, I drove home in silence with the radio off. After I got home and inside of my house, I immediately went to the bathroom. I proceeded to brush my teeth and take a shower to get rid of the feeling of a cock in my mouth, his saliva on my dick, and what i missed of his dried up semen on my stomach. I could feel that my asshole was very sore even though he only fingered me. After that I went on with my day as if it never had happen although I thought about it for the rest of the day. Tim and I would end up meeting 3 more times after this. The second time was in the back of a batting cage which was inches away from the woods so no one could see you at night time. The baseball field happen to the left of the library and also across the street from my high school. That time I ended up losing my anal virginity to him wearing a condom, sucking his balls and nipple for the first time, and cumming on a man’s face for the first time. The third time which as a sexual experiment we did role playing where I prostituted myself for $40 dollars. We had oral sex and he ejaculated on the side of my face on my cheek, not wanting to get it all over my face. The last and finally time I ever saw Tim in my life was when he came over to my house. This time we made a sex tape with my parents black and white video camera. We had oral sex, 69’d, I attempting to fuck him with a condom but he backed out because my dick was too big, and he rimmed me while I stood on my bed and jerked off and eventually cumming on his face. This time I didn’t let him come on me but instead watched him jerk off and ejaculate all over himself. After he wiped himself off we said our goodbyes and he left my life forever. Up until about 6 months ago we stopped talking on AIM and lost touch. I will forever remember him since he was my first for everything except fucking a man in the ass which eventually would happen with a 65 year old lawyer in a motel room. I’m not into old guys, I have been with men and women of all ages and races, but that’s just how it turned out for me. I would go on to hook up with over 2 dozen men and women but I was very smart and would use condoms for everything including oral sex and get tested out of fear for AIDS and STDS. So although you all now believe I’m bisexual I still consider myself straight due to the fact I only find women attractive and gay hook ups were only for getting off when I was either not sober or couldn’t get with a chick or both. Pretty much all the following hook ups would be from men I met on aim chats and eventually on craigslist when aim disabled its chats. This was my first time sexually with a man, hope you enjoyed.
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