My First Anal Experience
As a continuation of my prior story, Tom and I get into a routine everyday after track practice rushing to his house before his parent’s come home and pop in a video tape from his father’s porn collection. He has over a hundred on all subjects (straight, gay, tranny, lesbian, midgets, BDSM). Each day we choose a different tape never actually finishing one entirely. I still thing about this time because no one ever talked to me about sex growing up except my father telling me “wear a raincoat” with my old girlfriend - I learned a lot from watching those tapes.
After we put the tape on, we start to masturbate and eventually one of us is sucking the other or we jerk each other to see who could last the longest or shoot the furthest (Tom always could shoot the furthest). For me I always loved the warmth and taste of his cum. As we gain more experience with each other, we began to experiment more and start 69-ing and massaging the taint and asshole as we worked on each other. Massaging the taint just right would always gets my pre-cum flowing. I called him “Magic Hands”.
We actually talked about anal but did not attempt it due to the time and our fears of being caught. As the days went on, our fears subsided and we talked more about how hot it looked in the tapes. Finally it is Friday before President’s Day and we have off from school due to teacher’s training. We also have no track practice since we have a meet on Saturday morning.
I come over his house after my morning shower and after his parents left around 9AM. We go up to his bedroom. This was the first time I was in his bedroom as we always played around in the basement. He has a large bed, desk, dresser and various band posters on the wall. We have some small chit chat and start kissing and caressing. I am nervous but excited. He takes my shirt off and starting kissing and biting my nipples - they are so sensitive – I am so turned on and get fully erect. He starts rubbing me over my pants and I pull off his shirt. I slowly drop to my knees, suck on his nipples a little and then pull his pants down. He is also erect. I swallow his cock head and begin to work it. I now have gotten accustom to his size (9” long and 4.0” circumference – yes, we measured our cocks – mine was 6” and 4.5”, both cut) and just love the taste of his pre-cum while sucking his big purple head. I eventually pull his pants completely off but continue to suck on him with my right hand gently working him. I got a gag reflect and could never deep-throat him.
After some time (I had no concept how long), Tom pulls me up and slides down my pants and pulls them off. He starts sucking me and then pushes me back on the bed. We eventually rotate around getting into the 69 position. We both start playing with each other’s taint and asshole. I lick my fingers and start to slowly slide my index finger into his ass. He says, “Slowly please”. As I gently move in, he starts to moan and breath in a louder regular pace. I eventually slide in two fingers and he completely stopped sucking me, now moaning softly. I a gasping breathe he says, “fuck me – I got some lube from my mother’s vanity” pointing to his nightstand draw.
I am so erect and hard, excited, and nervous with anticipation. I flip him on his belly with his legs partially off the bed. I grab the lube and rub it generously over my cock. I slowly move in, and with my thumbs, I part his ass cheeks. He repositions himself getting on his knees and me standing. I slide the tip into him ever so slowly asking him is he okay and he simply nods his head. I finally get fully in him and I cannot believe the tightness around my cock. I slowly thrust back and forward his moans are increasing. Surprising to me, I am in my no cum mode – some days I can stay hard for over a hour – and today is one of those days – I am thrusting slow – hard – slow for a long time. He is moaning with pleasure. I am only focused on the task with my hands around his hips. I am enjoying watching my cock slide in and out. Finally, in a heavy breathe, he says “stop” and I pull out. My cock is dirty and I notice the sheets are a mess with his cum and anal fecal residue. I did not cum but am still erect.
We had a great time but now have a mess on our hands. Tom is a little panicked about the mess. I tell him we will wash the sheets and put the clean sheets back on the bed. Luckily, I grew up doing the laundry – one of my chores. After we loaded the washer, we went into the bathroom and showered together. In the shower, we are kissing and rubbing each other clean. He masturbates me eventually making me cum.
We are two brown hair tall lean guys (very twinky in today terms) that were totally inexperienced and naïve about anal sex. No real prep work – not cleaning ourselves inside and out- before tackling anal sex for the first time. Just a lot of passion. We also used an oil-based lube that stained the sheets.
As we waited for the clothes to dry, I read the label on the lube. It was for rectal thermometers and had a desensitizing agent. We laughter no wonder I could not cum, and I said something – like we will be better prepared the next time smiling at him. Thankfully, the sheets got cleaned. What surprised me was that we fooled around continuously for over three hours and is still a fond memory.
Over the next two weeks, we suck and masturbate each other daily. We finally got another day off; we plan to explore further and I am really excited. I actually did some reading in the school library about anal sex. It surprised me because they had about 20 different sex education books with a lot of information. This was before all the information on the Internet.
Once again, it is Friday – no practice and track meet on Saturday. This time I invite Tom to my house. His mother on the way to work drops him off and tells us to have good time playing video games and do not forget to eat. I can still hear her voice telling us to eat ☺
I am so horny and aroused we rush up to my bedroom that is smaller than Tom’s room with only a small twin bed and dresser with movie and sport posters on the wall. Before he arrived I took a hot bath and did an improvised enema on myself to make sure I was clean. I attack Tom as I have been thinking about nothing else but his cock since Wednesday night. Our clothes are off within seconds and our two aroused cocks are rubbing against each other as we kiss and fall on to the bed that I already took the blanket off and had some old towels on it. We are 69-ing it as this is our favorite position other than licking and kissing each other cum.
After some of caressing, rubbing and sucking, I tell him I want him – I am very nervous about his size but my horniness takes over. I hand him some lube that I got from the pharmacy. I get on my knees with elbows on the bed and feel him rubbing lube on my ass. He then slowly slides his finger (one – two I do not know) in me. No pain just chills from the excitement running over my body with a lot of nervous anticipation. He plays with my ass and asks if I am ready. Very nervous because of his size, I still say yes “take it slowly, be gentle” with a giggle. I will never forget the feeling of his cock entering for the first time – I could feel pressure and stretching but no real pain, just a little discomfort that disappears as he eases slowly into me as I breathe with every inch enters me. I could feel every inch and my asshole gripping him. He slowly begins to fuck me. I am just breathing and enjoying it with a few moans. After a number of strokes, he pulls out and flips me over on my back saying, “I want to see your face.”
He places my right leg on his shoulder and my other leg is on the floor as he stands at the edge of the bed, Tom enters me again but this time it feels completely different – no pain just arousal. My heart is beating faster and waves of pleasure come over me. He is hitting something that I never felt. With each thrust, pre-cum starts leaking out of my cock head – I never had these feelings - just waves of pleasure. Tom grabs my cock as he is thrusting faster and faster. I ejaculate hitting myself in the face. Tom keeps thrusting and leans over to lick some of the cum and kisses me. He fucks me a little longer saying “damn tight – I love it”. He pulls out and at the same time cums all over my belly, chest and face – one of his massive loads – three or four ropes. All I can think is where does all this cum come from? He lies down on top of me breathing heavy, kissing me and with his fingers feeds me some cum from my cheek.
We eventually get up and shower – no mess other than our cum on our bodies. Surprisingly we finished first and second in the 1500m race on Saturday. The first time I won a race.
Although adventurous, flexible and versatile in my sexual life, my experience has taught me that you really need to be turned on for anal sex and be into your partner.
After we put the tape on, we start to masturbate and eventually one of us is sucking the other or we jerk each other to see who could last the longest or shoot the furthest (Tom always could shoot the furthest). For me I always loved the warmth and taste of his cum. As we gain more experience with each other, we began to experiment more and start 69-ing and massaging the taint and asshole as we worked on each other. Massaging the taint just right would always gets my pre-cum flowing. I called him “Magic Hands”.
We actually talked about anal but did not attempt it due to the time and our fears of being caught. As the days went on, our fears subsided and we talked more about how hot it looked in the tapes. Finally it is Friday before President’s Day and we have off from school due to teacher’s training. We also have no track practice since we have a meet on Saturday morning.
I come over his house after my morning shower and after his parents left around 9AM. We go up to his bedroom. This was the first time I was in his bedroom as we always played around in the basement. He has a large bed, desk, dresser and various band posters on the wall. We have some small chit chat and start kissing and caressing. I am nervous but excited. He takes my shirt off and starting kissing and biting my nipples - they are so sensitive – I am so turned on and get fully erect. He starts rubbing me over my pants and I pull off his shirt. I slowly drop to my knees, suck on his nipples a little and then pull his pants down. He is also erect. I swallow his cock head and begin to work it. I now have gotten accustom to his size (9” long and 4.0” circumference – yes, we measured our cocks – mine was 6” and 4.5”, both cut) and just love the taste of his pre-cum while sucking his big purple head. I eventually pull his pants completely off but continue to suck on him with my right hand gently working him. I got a gag reflect and could never deep-throat him.
After some time (I had no concept how long), Tom pulls me up and slides down my pants and pulls them off. He starts sucking me and then pushes me back on the bed. We eventually rotate around getting into the 69 position. We both start playing with each other’s taint and asshole. I lick my fingers and start to slowly slide my index finger into his ass. He says, “Slowly please”. As I gently move in, he starts to moan and breath in a louder regular pace. I eventually slide in two fingers and he completely stopped sucking me, now moaning softly. I a gasping breathe he says, “fuck me – I got some lube from my mother’s vanity” pointing to his nightstand draw.
I am so erect and hard, excited, and nervous with anticipation. I flip him on his belly with his legs partially off the bed. I grab the lube and rub it generously over my cock. I slowly move in, and with my thumbs, I part his ass cheeks. He repositions himself getting on his knees and me standing. I slide the tip into him ever so slowly asking him is he okay and he simply nods his head. I finally get fully in him and I cannot believe the tightness around my cock. I slowly thrust back and forward his moans are increasing. Surprising to me, I am in my no cum mode – some days I can stay hard for over a hour – and today is one of those days – I am thrusting slow – hard – slow for a long time. He is moaning with pleasure. I am only focused on the task with my hands around his hips. I am enjoying watching my cock slide in and out. Finally, in a heavy breathe, he says “stop” and I pull out. My cock is dirty and I notice the sheets are a mess with his cum and anal fecal residue. I did not cum but am still erect.
We had a great time but now have a mess on our hands. Tom is a little panicked about the mess. I tell him we will wash the sheets and put the clean sheets back on the bed. Luckily, I grew up doing the laundry – one of my chores. After we loaded the washer, we went into the bathroom and showered together. In the shower, we are kissing and rubbing each other clean. He masturbates me eventually making me cum.
We are two brown hair tall lean guys (very twinky in today terms) that were totally inexperienced and naïve about anal sex. No real prep work – not cleaning ourselves inside and out- before tackling anal sex for the first time. Just a lot of passion. We also used an oil-based lube that stained the sheets.
As we waited for the clothes to dry, I read the label on the lube. It was for rectal thermometers and had a desensitizing agent. We laughter no wonder I could not cum, and I said something – like we will be better prepared the next time smiling at him. Thankfully, the sheets got cleaned. What surprised me was that we fooled around continuously for over three hours and is still a fond memory.
Over the next two weeks, we suck and masturbate each other daily. We finally got another day off; we plan to explore further and I am really excited. I actually did some reading in the school library about anal sex. It surprised me because they had about 20 different sex education books with a lot of information. This was before all the information on the Internet.
Once again, it is Friday – no practice and track meet on Saturday. This time I invite Tom to my house. His mother on the way to work drops him off and tells us to have good time playing video games and do not forget to eat. I can still hear her voice telling us to eat ☺
I am so horny and aroused we rush up to my bedroom that is smaller than Tom’s room with only a small twin bed and dresser with movie and sport posters on the wall. Before he arrived I took a hot bath and did an improvised enema on myself to make sure I was clean. I attack Tom as I have been thinking about nothing else but his cock since Wednesday night. Our clothes are off within seconds and our two aroused cocks are rubbing against each other as we kiss and fall on to the bed that I already took the blanket off and had some old towels on it. We are 69-ing it as this is our favorite position other than licking and kissing each other cum.
After some of caressing, rubbing and sucking, I tell him I want him – I am very nervous about his size but my horniness takes over. I hand him some lube that I got from the pharmacy. I get on my knees with elbows on the bed and feel him rubbing lube on my ass. He then slowly slides his finger (one – two I do not know) in me. No pain just chills from the excitement running over my body with a lot of nervous anticipation. He plays with my ass and asks if I am ready. Very nervous because of his size, I still say yes “take it slowly, be gentle” with a giggle. I will never forget the feeling of his cock entering for the first time – I could feel pressure and stretching but no real pain, just a little discomfort that disappears as he eases slowly into me as I breathe with every inch enters me. I could feel every inch and my asshole gripping him. He slowly begins to fuck me. I am just breathing and enjoying it with a few moans. After a number of strokes, he pulls out and flips me over on my back saying, “I want to see your face.”
He places my right leg on his shoulder and my other leg is on the floor as he stands at the edge of the bed, Tom enters me again but this time it feels completely different – no pain just arousal. My heart is beating faster and waves of pleasure come over me. He is hitting something that I never felt. With each thrust, pre-cum starts leaking out of my cock head – I never had these feelings - just waves of pleasure. Tom grabs my cock as he is thrusting faster and faster. I ejaculate hitting myself in the face. Tom keeps thrusting and leans over to lick some of the cum and kisses me. He fucks me a little longer saying “damn tight – I love it”. He pulls out and at the same time cums all over my belly, chest and face – one of his massive loads – three or four ropes. All I can think is where does all this cum come from? He lies down on top of me breathing heavy, kissing me and with his fingers feeds me some cum from my cheek.
We eventually get up and shower – no mess other than our cum on our bodies. Surprisingly we finished first and second in the 1500m race on Saturday. The first time I won a race.
Although adventurous, flexible and versatile in my sexual life, my experience has taught me that you really need to be turned on for anal sex and be into your partner.
3 года назад
